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Holiday Homes in Siesta Key

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    Travellers to Siesta Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 756 Rentals in Siesta Key
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    Gulf Side Siesta Key Villa~Peaceful 1st Floor Villa, 3 pools-Jamaica Royale #1001 / 35
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Ebb Tide #8 1 Bdr/2 Bath Fall Openings1 / 23
    (28)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Updated Townhouse!  Private access to Beach. Enjoy Tennis, Heated Pools, Fishing1 / 38
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    15 min. walk/3 min. drive/free shuttle to Siesta Key! Best rates for a 2bdr/2bth1 / 30
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2017
    Very clean and updated rental. Had everything we needed and more, nice screened in patio to relax on as well. Even though it’s not on beach, very close to everything to enjoy...
    Reviewed 17 November 2017
    This place was exceptional clean and well maintained. Beaches are literally right around the corner. I would recommend anyone visiting the Seista Keys area to check this place out!
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    About this property
    All new! This spacious, 2 bedroom/2 bath has everything you need for a relaxing and fun vacation in Sarasota, just minutes to Siesta Key. Relax in comfort with all the amenities: - Fully equipped Kitchen with all new appliances, dishes, glassware, etc. - Top quality, brand new queen size beds -...
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    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beachfront Getaway in Siesta Key1 / 28
    (16)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2018
    This was our second time staying in this modern, clean, and peaceful condo, just steps from the beach, beautiful blue water and powdery white sand and we loved it again! We are...
    Reviewed 25 May 2018
    Everything about this condo was perfect! It had plenty of space for our family of 5 (baby slept in a pack n play.) It was very nicely updated and decorated; we all loved the...
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    About this property
    This luxurious one story townhouse was newly renovated and has its own private access to the #1 beach in the US merely steps away from the front door. It boasts all the luxury you'd expect from a beach house! Modern kitchen, contemporary bathroom with walk in rain shower, luxurious bedroom and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Top Siesta Key Location, The Village Studio - Eat Shop Beach!1 / 32
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Patio
    • Waterfront
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2017
    We loved walking everywhere - the beach, especially every sunset; shops, great food. The condo was lovely, and the setting enriched by the other owners in the complex.
    Reviewed 25 March 2017
    We enjoyed our 3 day stay. A longer stay would require a larger place but it was perfect for this time. Our host was very helpful and had a nice gift awaiting our arrival :)
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    About this property
    A Gertrude Rentals property. Enviable location just steps away from everything! The Siesta Key Village Studio is an accommodating ground floor, one-room efficiency apartment perfectly nestled on a quiet tropical street between the best beaches, shopping and dining on the island. Wander one...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Top  Location on Siesta Key - Gertrude's Village House1 / 50
    (30)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2017
    My son booked this for his whole family. There were nine of us. The beach was just a half block away. It was beautiful with cool white sand, aqua water with warm rolling...
    Reviewed 25 September 2016
    Stayed there, the location is great. Everything in walking distance. The kitchen was supplied with everything you need. The positives beyond location varied, quiet, lots of room...
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    About this property
    A Gertrude Rentals property! Our Top Location! Leave the car behind. Richly furnished, perfectly nestled between the best beaches, shopping and dining on the Island, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. Our living room, master bedroom and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Honeymoon Suite - Gulf views - next to Siesta Key Beach1 / 21
    (6)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2018
    The suite was lovely, and the bed was very comfortable. The grounds and pool were very well maintained. Great Beach access.
    Reviewed 3 August 2016
    Me and 2 friends booked this wonderful appoartment very short-term (the day before) and the owner Virginia was just amazing. She helped us with the booking, welcomed us...
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    About this property
    Gumbo Limbo Vacation Rentals: Honeymoon Suite, 60 steps to the BEACH. NEWLY REMODELED AND REFURBISHED. Spacious 1 bedroom / 2 full baths townhouse (850sq/ft) over 2 floors, with 1 King size bed, and a luxury Queen self inflating air bed for max. comfort. This townhouse also offers 2 balconies...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Siesta Key 2 BR, 2 1/2 Bath - *Across From Beach - Pool-view* - Newly Renovated1 / 49
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Washer
    • Secure Parking
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 October 2017
    Lovely condo - great for a Ladies' Weekend Away! Very spacious and clean. It was easy to get to town and the beach using the Frog Hopper FREE taxi service! Washer and dryer was...
    Reviewed 11 August 2017
    The location is family friendly and close to everything . Very nice pool and very clean condos. Excellent management team . Very eager to help you to have the best experience...
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    About this property
    Steps to Siesta Beach and a Gorgeous Condo, Bring the Entire Family! #1 Beach in the US (2017) : Siesta Key is the United States #1 Beach Boasting Miles of Powder White Sand and a Charming Village loaded Shopping, Dining and Ice Cream :) Our 2 bedroom 2.5 bath unit has everything you need for...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Siesta Key -  2bdrm on the beach - amazing views!!1 / 27
    (29)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Our stay was just fantastic! Loved every minute and the condo was perfect for RNR! I will recommend the condo without hesitation. Husband and daughter loved to fish off the...
    Reviewed 5 weeks ago
    Our trip was absolutely wonderful!! The owners were very accommodating and quickly responded to any questions. We will definitely be back!!!
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    About this property
    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Beachy Chic Condo in Siesta Key - Waterfront - Free wifi - Sleeps 4 !1 / 29
    (18)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2018
    Nothing negative to say here. Location was great, condo was spacious and had everything we needed. I would definitely book to stay here again!!
    Reviewed 22 June 2018
    We will return to the Beachy chic Condo !! Loved the location, easy to walk to shops and restaurants (.25 mile away) . Sunrise was spectacular from the dock on the inter coastal...
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    About this property
    Welcome to our Condo in Siesta Key ! Located on the inter-coastal Waterway and a short walk to the whitest sand and the # 1 beach in the USA. This 1 bedroom Condo is a great retreat for anyone looking for a beautiful Island getaway! Our condo is on the 2nd floor (sleeps 4) We are on Siesta...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Island Suite ' Next to Siesta Key Public Beach'1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We thoroughly enjoyed everything. No complaints whatsoever. Can't wait to come back. So conveniently located near beach and everything. Loved it.
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    About this property
    ISLAND SUITE #5610 (sleeps 6, ground level), a 2 bedroom + den apartment of 1,200sq/feet that can accommodate 6 people comfortably in beds. This suite offers 1 king and 2 queen size beds (1 queen is in the den), 2 full baths and a large breakfast patio. We are located right across the street from...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Banyan - A Tropical Retreat in Paradise1 / 25
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 April 2018
    The Banyon is a remarkably beautiful and comfortable home. There are many private seating areas inside and out. The kitchen is fully equipped; the beds are very comfortable and...
    Reviewed 12 August 2017
    We loved this place! It was so private you felt like you were in your own world with the surrounding trees and tropical landscaping, yet close to most everything. The home was...
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    About this property
    View of Roberts Bay / Near Beaches / Great Shopping & Dining Get lost in the intoxicating relaxation of Siesta Key, in this luxurious private home. This tropical retreat is a single-family residence located at the end of a secluded dead end street in the opulent neighborhoods of northern Siesta...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Direct Beachfront Siesta Key Condo with Amazing Views of the Gulf!1 / 37
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Central Heating
    • Ocean Views
    • Balcony
    • Terrace
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    We love everything about this beautiful condo. The location is just steps to the most beautiful beach in the US. Sit on the lanai and watch the sunset and see dolphins swim by...
    Reviewed 21 March 2018
    We had a wonderful time and enjoyed our holidays a lot at the beach condo. It was super clean, perfect funitured, and it was like coming home. we are looking forward to coming...
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    About this property
    IMAGINE SPENDING AN ENTIRE MONTH TO UNWIND, REJUVENATE AND HAVE FUN BY THE SEA. HEAR THE WAVES AND WATCH THE DOLPHINS SWIM BY FROM THE BEACHFRONT LANAI. NO ELEVATORS, JUST STEPS TO THE BEACH AND THE POOL. LOCATED ON THE VERY BEST PART OF CRESCENT BEACH WITH ITS FINE, WHITE SAND. SERENITY BY THE...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2018
    I stayed over the winter holiday with my husband and other adult family.It was the perfect place to have a pleasant vacation. Close to all shops and downtown and also a short...
    Reviewed 6 September 2017
    What a beautiful modern and superbly located house. Immaculate and well maintained with everything you could possibly need. Our host Randy was excellent and answered our...
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    About this property
    Steps from the islands best restaurants, shops (in the Village area) and a short walk to the #1 beach in the USA! Great home with 2 car and 1 car private garages. Recently renovated including a screened in patio, hot tub and pool. Brand new appliances making this home a great place for monthly...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront- Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2018
    Such a well appointed condo, with a fabulous location right on the beach.Easy walking distance to some great restaurants. Our owner was very attentive and answered all...
    Reviewed 14 November 2017
    We loved this condo. The beach was wonderful. Siesta Key Village was so close with great restaurants to choose from... Pavan was very nice to work with. What more can you ask...
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    About this property
    - Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you can get to the Gulf without...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front1 / 20
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Central Heating
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2017
    We absolutely loved this little condo on the beach. Our foursome vacations together at least once a year. We love the Gulf coast and are only interested in beachfront rentals...
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    About this property
    Description Details Features Inquires Similar Listings google-map-thumb Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front USD 160 Per day 6312 Midnight Pass Rd., Siesta Key slider PreviousNext Property Description Relax in this beautiful fifth floor beach front Condo...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Jamaica Royale #92 on the #1 Beach in the USA!1 / 12
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Porch
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 February 2018
    After reading some of the reviews we were somewhat nervous. The resort was clean and staff was friendly. Our condo in Tower II was found clean and had a great view of the gulf...
    Reviewed 13 August 2017
    We came in around 5pm. I thought its ok not to call because they said in the email that the key will be left in the lockbox. No key when we got there. We had to call and after...
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    About this property
    Jamaica Royale condo #92. Located at the #1 BEACH IN THE USA, this 2 bedroom, 2 bath garden view unit has everything you need! It is located in the garden area of our beautifully landscaped property. It has new furniture and is freshly painted, with tile floors in the living areas and carpet in...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grand accomdation on USA #1 Beach  - Siesta Key Fl1 / 32
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Sauna
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Children's Pool
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harbor Towers Yacht and Racquet Club Unit 503 provides one of the best views in the building (fifth floor facing south/east). The glass enclosed Lanai with floor-to-ceiling sliding glass doors provides bright sunlight during the morning and afternoon with excellent views of the intercostal water...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Newly Renovated Waterfront Condo w/Beach Access1 / 21
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Balcony
    • Washer
    • Parking
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 2017
    A really lovely apartment, very well equipped. location is perfect if you want a peacful beach holiday.Turtle beach is stunning and great for fishing, swimming and collecting...
    Reviewed 18 April 2017
    This is a wonderful 2-bedroom, 2 bath condo overlooking the bay. The nicely decorated lanai is a great place to relax with your morning coffee. The kitchen is wonderfully...
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    About this property
    Our 2nd floor, end unit condo was completely renovated over the winter of 2012– 2013. The floor plan was opened up to provide a nice airy feel and to enjoy the water view. All furniture, flooring and fixtures are new. The entry hall has a bench to store your flip-flops and other beach gear and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sunset Point Siesta Key FL  AWESOME RENTAL !!1 / 27
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Sauna
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    Could not have a better location. Steps from the sand with the village in walking distance. The beach house is a great place to stay. Everything you need. We very much enjoyed...
    Reviewed 8 July 2017
    This location is absolutely perfect! It is on the most beautiful beach and steps to an adorable village with several restaurants, shops and all the amenities you could need. It...
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    About this property
    Beach and water front on Gulf Of Mexico. A block from Siesta Key Village for lite and fine dinning, fun, shopping and nightlife. Two Master Suite King Bedrooms with Master Bath for each. Sauna, four Mexican tiled decks with panoramic views of the Gulf and beaches. Fishing Pier. Leather, stone...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Tiny House Siesta - Yellow Lifeguard Stand Tiny House1 / 32
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2018
    We were 4 adults that stayed for 2 nights. The little houses are only five mins drive from the glorious beach.Though compact the houses have everything (except a hairdryer...
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    About this property
    Imagine Yourself At (Tiny) Home: Beach life is best! Enter through the bright yellow, life-sized replica of a Siesta Key lifeguard stand, and drop your beach bags on the two stools beneath our surfboard-shaped breakfast bar. Passing through the living room, decorated with just a touch of...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Best in Siesta Village! 1.5 blocks to best beaches! - Casa Van Lopik (Canal)1 / 48
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Waterfront
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2018
    This was the perfect place for eight fabulous women who were celebrating life. The beds were comfortable and the rooms spacious. The hot water plenty. It was a plus to have...
    Reviewed 7 March 2017
    Location is the best thing about this condo -- short walk to beach and to Siesta Key Village. Very convenient. Another big "pro" was Daniel. The owner is very...
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    About this property
    A Gertrude Rentals property! Large 3BR home perfectly located between the best beaches, shopping dining and entertainment on Siesta. Leave the car behind. After the beach, you could wander to town for fresh oysters and seafood, drinks, live music or ice cream, or just relax in a tropical garden...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment1 / 16
    (23)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Porch
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2017
    Siesta key is a wonderful place to stay ,And this apt was the cherry on top, minutes from the beach and village area,Not only where the accommodations great , they have bikes...
    Reviewed 29 April 2016
    Traveled with business associates & spouses, combining business & pleasure.Great ;location for both business in Sarasota as well as amenities of Siesta Key.Very well...
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    About this property
    This lovely 2BD/1BA apartment is located just 1 mile from beautiful Siesta Key Beach. Siesta Key was rated the #1 Beach in the United States by Dr. Beach (2011) and the #2 Beach in the U.S. in the 2013 TripAdvisor Travelers Choice Awards. Siesta Key was listed in 2014 by Smarter Travel.com as...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Key West Suite next to Siesta Key Beach1 / 32
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Jus stayed one night and it was really enjoyable. Accommodation was really nice and just across the road from the beach. Hope to return someday.
    Reviewed 3 weeks ago
    We loved our week in the Key West Suite at Siesta Key. The apartment is the top half of what probably used to be a garage for the larger house beside it. The suites share a...
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    About this property
    2 apartments to choose from: Key West Suite A relaxed beach experience. This cozy two bedrooms & den apartment, full 2 baths (1 King bed + 2 Twins + 1 Queen) 1,200 sq/ft. suite on second level with two private balconies and partial Gulf view from the den. This apartment is fully furnished and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach Walk Townhouse1 / 16
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We had a great time. Very close to beach and within walking distance to many restaurants. The place was clean and as advertised.
    Reviewed 21 May 2018
    The space was great. Very close to Siesta Key Beach. The only thing is that it is a 3 floor duplex and it makes it kind of difficult bringing your stuff up the stairs.
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    About this property
    Spacious Beach Getaway (sleeps 6), Calle del Otoño unit D, a 3 bedroom / 2.5 baths townhouse of 2,000sq/feet which is located right next to Gumbo Limbo. It offers 1 king, 2 twins and 1 queen size bed, brand new carpeting (January 2016), a balcony with partial Gulf view and a heated pool. This...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Charming Siesta Key Condo, Walk to Beach, Pool1 / 29
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Wi-Fi
    • Parking
    • Sauna
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 May 2017
    The location is perfect, the beautiful white beach of Siesta Key is on your doorstep. If you feel energetic it is a brisk 25 minute walk into the village from the condominium or...
    Reviewed 11 July 2016
    Very short walk to the beach! Sue is so friendly! The condo was in excellent condition! We will definitely stay here again!
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    About this property
    Spacious Condo on Siesta Key with 2 Queen Beds is beautifully furnished, all new, and super clean! WALK RIGHT OVER TO THE #1 BEACH IN AMERICA, you do not need a car on this vacation stay. And if you want to see the rest of Siesta Key you can take the free shuttles, and the new Siesta Key Trolley...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    -Hide-A-Way Suite- next to Siesta Key Beach1 / 18
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Waterfront
    • Patio
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 April 2017
    Great location to beach and town. Well maintained and attention to your needs. Onsite pool and outdoor space is beautiful. Great stay.
    Reviewed 13 April 2017
    Very happy with choice, across the street from beach, and very close to the village! Found some wonderful bars and retaurants!
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    About this property
    HIDE-AWAY SUITE # 664B (sleeps 4, ground level, sqft 580.00) this apartment has been completely remodeled July 2015. This 1 bedroom / 1 bath apartment, offers a king bed plus and a luxury self-inflatable Queen size Air-bed and 2 flat screen TV’s. This suite offers a full size new kitchen and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (2)1 / 43
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 February 2017
    What a wonderful stay! To start, Daniel is a very down-to-earth guy....ALWAYS responded promptly to phone calls and emails, and always was always courteous and complete in...
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Hibiscus Suite -Best Beach Location of Siesta Key-1 / 16
    (1)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    We were there for 5 days for our honeymoon and the place were very nice! Looks just like the picture and was very clean. The first two days were a tues and Wednesday so it was...
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    About this property
    HIBISCUS SUITE # 662B (sleeps 4, ground level, sqft 580.00) - Spacious 1 bedroom studio apartment(580sq/ft) ground floor, with 1 King size bed plus and a luxury self-inflatable Queen size Air-bed and 2 flat screen TV’s Bath features a walk-in rain-forest shower and washer and dryer. This...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)1 / 49
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Balcony
    • Patio
    • Wi-Fi
    • Porch
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2016
    While ratings and reviews are subject to personal taste, we found this property average at best. The positives included a nice size home, 3BR, 2BA, 2 blocks to the beach and...
    Reviewed 4 December 2015
    Our extended family of 7 with 4 adults and 3 children, stayed 4 nights at this property. We were thrilled to see that the grocery store was at the end of the street, as were all...
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    About this property
    Casa Van Lopik (jardin), our garden facing suite, is a large 3BR home. Brought to you by Gertrude Rentals! Perfectly located between the best beaches, shopping dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but always...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (21)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2018
    Had everything we needed. We appreciate Joe the maintenance guy checking on us. He was very helpful. Would stsy here again.
    Reviewed 6 June 2018
    Firstly, let me say we've never booked a place which wasn't a hotel or a resort. So this was new for me. I found tripadvisor very helpful and Sandy Toes Siesta Key was a...
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    About this property
    A short stroll down a private road to the #1 Beach in the US. You will love the location - you are located in the Resorts of the SaraSea community and can walk to everything you might need or want... Grocery, restaurants, ice cream, pizza, sports rentals, drugstore or boat rental. You have your...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedroom  2 Bath  Home in Siesta Village1 / 9
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • DVD Player
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2017
    This was by far the best place we have stayed at in Siesta Key. The house was clean and had everything we needed to have a great vacation. We could not have ask for a better...
    Reviewed 10 July 2017
    Our family of 6 stayed for 3 nights and we couldn't have been more pleased. This is a clean and very nicely equipped home with just about everything we could need for a beach...
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    About this property
    This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located within the heart of Siesta Key Village and a block away from the famous Siesta Key Beach. Walk to everything, yet have privacy of a home. It is newly renovated with all new furniture and beach house décor. This home is equipped...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Crescent Arms 703S, Beachfront Penthouse, Gulf View from Every Room! 2BR-BA1 / 40
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2018
    This condo is in a great location, steps from the beach with an amazing view of Point of Rocks. This is our second year renting from the owners who are great to work with. Very...
    Reviewed 18 June 2018
    Pavan and Tracy are very attentive and accommodating. During our stay we needed nothing. the Condo is well appointed, nicely furnished and had everything we needed, including...
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    About this property
    -Accommodations: Condo, 2 Bedrooms + Convertible Bed, 2 Baths (Sleeps 4-6) -Expansive, panoramic gulf view from every room of this 7th (top) floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Spacious 4bed air-con villa on Siesta Key1 / 26
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Parking
    • Grill
    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2016
    This lovely 4-bed villa was well proportioned and kitted out for our party of 6 adults but deciding who should get the biggest and best bedroom with the only en-suite could have...
    Reviewed 22 July 2015
    We stayed two weeks here and had a wonderful time. The villa was very spacious with large bedrooms, eat-in kitchen and living rooms. Most impressive was how well equipped it...
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    About this property
    Very spacious, air-conditioned 4 bed detached ranch-type Villa on Siesta Key Bayside. Sleeps 8, 1 King, 1 Queen, 2 Full and 2 twin beds. 1 month minimum Jan-March, 2 week minimum April -Dec. Maximum 3 cars . Large Heated Communal pool, Own Outdoor patio area with BBQ , Table, seating and sun...
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    Location Information
    Siesta Key, Florida FL34242
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (3)1 / 42
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2018
    This place was amazing and could not have been more perfect to stay at for an extended vacation!!!! The unit was cozy and comfortable- it had everything that you could possibly...
    Reviewed 9 April 2018
    Great location! Only steps to beach access. Our unit was very clean and had all we needed for 2 people. The owner Daniel, was great to work with. He always replied to any...
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2018
    Everything was great. The condo was updated, clean and spacious. It had what we needed to really enjoy our week. It was a quick walk to the beach, restaurants and shops. We...
    Reviewed 26 March 2018
    We had so much fun. It was so nice that the kids had their own space , own TV, own bathroom. The beach is amazing. The owner provided beach towels, chairs and umbrellas. I...
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    About this property
    A spacious 2 bedroom 2 bath Townhouse, with a 2 car garage and extra guest parking. Stroll down a private road (about 300 yards) to the #1 Beach in the U,S. You are in the Resorts of Sara Sea and just a couple of blocks from restaurants, grocery, sports rentals and ice cream ! The Great room has...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Villa Palma - 35% Off Late Summer Special1 / 21
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 November 2016
    We had a great time at Villa Palma. The villa is very clean and it has everything you need for your stay. It is very close to the beach, we ended up only going to the beach. The...
    Reviewed 11 August 2016
    What a LOVELY place to stay!!! Sean was flexible, attentive and accommodating, and there was even fresh fruit, sparkling water and a personalized welcome sign waiting on the...
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    About this property
    Villa Palma is a stand-alone single story villa located in the beautiful Polynesian Gardens community, on the beautiful barrier island of Siesta Key, Fl. The home is chic and hip in its mid-century modern beach cottage decor and schictyle. The newly renovated kitchen is sleek in design and...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Bay Views - Private access to Beach. Enjoy Tennis, Heated Pools, Fishing1 / 50
    (12)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Grill
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    • Sauna
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 December 2017
    Beautiful beach and spacious condo with all amenities at your doorstep, enjoyed tennis , pool and exercise room and outdoor gas grill right across street yet still very private...
    Reviewed 21 November 2017
    We had a wonderful vacation stay in this condo. It was spacious, clean and had beautiful views of the waterway. We really enjoyed having our morning coffee watching the boats go...
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    About this property
    Gulf & Bay Club Bayside is a gated resort community is across the street from our private access to - Siesta Key Beach with the world renowned white sands - rated one of the top ten in the US! FREE High Speed Wireless Internet ! - just bring your Laptop. Watch the boats float by! Just steps from...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Beach, Pool  And Walk To Siesta Key Village1 / 36
    (6)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Grill
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2017
    I could not believe how close this is to everything we wanted to do! It was quiet and serene! Sunsets were amazing, just around the corner and short walk to a cute little beach...
    Reviewed 22 August 2014
    all people are going to take this one way or the other .we wasnt looking for a fancy place with wifi and all of that because u are on vacation . and its a time to enjoy . not...
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    About this property
    What a great location! walk to Siesta Key village or relax on your small Gulf Beach or fishing on the pier at Sandy Cove. This 2 bedroom 2 bath unit is a 2nd level condo with pool views from the balcony. Enjoy breakfast after a short walk at one of the villages' quite restaurants before...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Excellent Location - Gulf/Beach View - Siesta Key1 / 26
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 November 2017
    The condo at Sunset was fantastic. The location is right across the street from the Siesta Key beach and you have a view from the condo as well. The white sand is beautiful...
    Reviewed 24 October 2017
    We thoroughly enjoyed our stay at this beautiful condo unit. The location was fabulous, directly across the street from the beach! The condo was very clean, beautifully...
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    About this property
    This vacation rental offers a full view of Siesta Key Beach/ The Gulf upon entry; relax and enjoy from your lanai or master bedroom. The property has been newly transformed to accommodate our guests best welcome to Siesta. From the comfort of the home décor to your fully stocked kitchen: cookware,...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated1 / 21
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Housekeeping Included
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2018
    The Sea Club condo was fabulous!! The location, being on the inner coastal, watching the boats every day and night go by, was perfect. Loved to watch the others fishing off...
    Reviewed 17 June 2017
    The apartment is on the waterway side of the key and is great if you want to fish. The walk to the beautiful beach is only a 10 minute walk away. The apartment is clean and...
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    About this property
    Our condo has just been remodeled with granite counter tops, stainless steel appliances, dishwasher, cabinets, new tile, new bathroom, and new furniture. It is a second floor unit. We have included all the essentials for a family that likes to have the flexibility to make meals at 'home' or...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (1)1 / 47
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Patio
    • Cable/satellite TV
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Wonderful, relaxing, perfect location! On the quiet side of the key, easy close access to gorgeous crescent Beach. Easy quick walk to bus stop and local market, restaurants as...
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    About this property
    Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8). Brought to you by Gertrude Rentals! Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Top Floor End Unit Directly Across the Street from Siesta Key public beach1 / 10
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 February 2018
    Very clean, great owner, super location, great value. My family with kids loved this space. Pool and clubhouse was nice as well.
    Reviewed 15 July 2017
    We loved our stay here, the owner was very nice and easy to work with. Her place was clean with lots of amenities. Great view of the beach and short walk to the white powdery sand.
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    About this property
    2 bedroom/2 bath top-floor end unit steps from the #1 beach in the County and #3 in the World (voted by Trip Advisor Feb. 2016). Sarasota County spent almost $30 million renovating all of the public facilities - new concession, bathrooms, SunDeck Restaurant, playground equipment and picnic...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Our Beach House1 / 17
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2016
    Just back from our trip to Siesta Key with my Husband and 4 kids where we spent a lovely relaxed week at 'our beach house'. The house was fully equipped with everything a...
    Reviewed 9 May 2016
    "Our Beach house" on Siesta Key is a very comfortable, very clean and well taken care of property. It is in a quiet residential neighborhood with beach access just...
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    About this property
    OUR BEACH HOUSE (right behind the Cottage) (sleeps 6) Fully renovated in the late summer of 2013, this spacious, enchanting 3 bedroom/2 full baths ground-level property of 1,100sq/feet offers 1 King, 1 Queen and 2 Twin beds. You will be in close proximity to Siesta Beach and to Siesta Village. The...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Palm Oasis - Relax in Comfort -1 / 35
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    For a large family that has not been on vacation sometime, this was ideal. Walking distance to beach and to village as well as the amazing salt water pool. With 3 children under...
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    About this property
    The Palm Oasis is a 4-bed single family home with 2,000 sq. ft. located only 1 block away from Siesta Key Beach. This home is on one level and has all the amenities including a brand new salt-water pool which is the center of the backyard and a outdoor BBQ grill with a bar to enjoy your fabulous...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Children's Pool
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Patio
    • Sauna
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a large, bright and clean 2 bedroom and 2 bath first floor Condo. Being first floor gives you extra entrance through patio or lobby. Also one of the few condos with a private patio with new furniture to enjoy the beautiful weather and view. Condo clean and bright and beautifully decorated....
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Steps to Sand Path of Siesta's Best Beach! - Old Man and the Sea Inn (4)1 / 47
    (34)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2018
    Great location. Steps away from beach, short walk to restaurants, free shuttles to the village. Clean condo.
    Reviewed 12 September 2017
    We stayed for a long weekend and couldn't have been more pleased. Their team has thought of everything- all you need to do is sit back and enjoy the amazing location and town...
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    About this property
    A Gertrude Rentals Property! Rated 'The World's Finest, Whitest Sand' at the Great International Sand Challenge. Perfect for travelers in search of uncomplicated seclusion. Residing in Siesta Keys most 'private' non-private beach neighborhood and just one marlin's length (5 steps) from yard to...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Exceptional townhouse - Royal Palm Suite - with Gulf Views from all 3 balconies1 / 26
    (24)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2017
    Great fit for small or large group with two bedrooms and a third semi-private on the top floor with its own balcony. There is a balcony on each of the three levels and all have...
    Reviewed 31 March 2014
    Six of us, ages 7-70, stayed in the Royal Palm Suite, #662 of Gumbo Limbo for 1 week during Spring break. The house is clean, comfortable, has lots of space and views of the...
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    About this property
    The Royal Palm Suite (sleeps 6) is a 3 bedroom luxury townhouse of 1,850 sq/feet over 3 floors, 2 kings and 1 queen size bed, 3 balconies (each has a Gulf View), almost all rooms have a Gulf view, a kitchen with granite counter tops, master bathroom offers a bathtub with Gulf view and a bidet....
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Crescent Cottage1 / 16
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2016
    Very cozy but good for 1-2 people. Walk to private beach and pool. Only thing - can be quite noisy at night with the bar across the street but otherwise great
    Reviewed 6 July 2016
    Old Florida vibe, love it. Short walk to beach! Perfect size place for my husband and I and our 60 lb lab. The private fenced grassy area in backyard was perfect for our dog...
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    About this property
    PET Friendly! This one bedroom and one bathroom beach bungalow is located 150 yards away from the beach. You can walk to restaurants, shops and a great pool area. Queen bed and a sleeper sofa make it possible to sleep four. Enjoy your morning coffee on your private screened porch or while you walk...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1
    Siesta Key Holiday Rentals

    Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key holiday rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theatre, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.

    Lions, Tigers & Circuses

    When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.

    Gardens & Aquariums

    Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.

    Locomotives & Science

    Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theatre, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.

    History & Baseball

    From your money-saving Siesta Bay holiday rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.

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