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    Travellers to Siesta Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    108 Matching Rentals in Siesta KeyView all 895 rentals
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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh1 / 38
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Canal Home on Siesta Key w/ Pool, Wifi, Renovated 1950 Style Sarasota School of1 / 37
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This is a large nice home. But it needs basic maintenance. Many light bulbs out, pool deck paint peeling, caulking painting needed, etc. In addition,not enough bath towels...
    Reviewed 16 November 2018
    This house is perfect for your Siesta getaway!Close to Village and #1 beaches great pool on the CanalI would defiantly stay here again!
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    About this property
    You will Never Want to Leave this Upscale, Mid-Century Modern, 4 bedroom Pool home with Salt-Water Canal Views and seawall on Siesta Key!!! This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, 'Sarasota School of Architecture style' pool home is conveniently located...... only a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 20
    (4)Excellent
    2 Bedrooms, 3 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 19 February 2019
    We had such a great experience with this rental. The house was beautiful, perfect for a family with a small child (ours was about 15 months old). And you can't beat the location...
    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...
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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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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front1 / 20
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2019
    The location and views were great. The shuttle is easy to catch and the beach is pristine. The condo itself was not very clean when we arrived. We found candy wrappers on the...
    Reviewed 15 August 2018
    This condo is right on the beach. If you are looking for a family friendly place this is it. We absolutely loved this place and the view ..OMG is AMAZING!!! The place was well...
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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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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    The Shells Villa - Next to Beach & Village1 / 41
    (69)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2019
    We stayed here with our family, seven of us all together, including 3 children (5, 8 & 11). Big place! Lots of rooms and never felt crowded at all. Lots of stairs too but...
    Reviewed 16 May 2019
    This was a lovely place to stay! Very spacious and charming place. It was well stocked with towels and we loved having a washer/dryer on site. There were 5 beach chairs that...
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    About this property
    3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach....
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (12)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2019
    The house at Siesta Key was perfect for our family. There was plenty of space for everyone to spread out and enjoy the week. The pool and fishing dock worked wonders for the...
    Reviewed 14 July 2019
    The house was perfect for our large family! The Pool was a huge hit with the little ones on those cloudy/rainy days, well really the whole week. The walk to the beach is maybe 5...
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    About this property
    Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
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    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover Siesta Key at this three bedroom two bathroom vacation rental home located in the heart of Siesta Key tucked away in a quiet neighborhood. Hire one of the many free ride services on the key for a quick trip to visit Siesta Key village where you can find a multitude of restaurants,...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Walk to Village, Heated Saltwater Pool,  Bike/Walk to Beach, WiFi/Cable, Custom1 / 34
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Mermaid is located less then 1/2 mile and less than a 10 minute stroll from Siesta Key Village. It's a 12 minute walk to the beach and the crystal sands and sparkling waters of the Gulf of Mexico on Siesta Key. Walk to our local gourmet grocery store for freshly prepared sushi, or for a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 46
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2019
    This was our first experience using trip advisor and would highly recommend it! We stayed at this beautiful home on the beach for a week. Along with the fantastic views, the...
    Reviewed 29 September 2018
    We had a wonderful stay at Siesta Keys Florida. David ‘s home is beautiful and well maintained. It does have several bests of steps if you have any kind of handicap. My husband...
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    About this property
    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the Gulf & beach. The entire back of this house opens...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (22)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 18 August 2018
    The house was nice and spacious along with a garage for your car. You are walking distance to restaurants and stores. And just a couple minute walk to white sand beach. They had...
    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.
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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
    2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach1 / 13
    (5)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 9 March 2019
    Fabulous location! 1 block from the beach and 1 block from the Village. Very clean! Returning again next year
    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...
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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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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Palm Oasis - Relax in Comfort - 1 rental per calendar month1 / 35
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    This was a family vacation that had been planned for months. We were unaware of the red tide until a few weeks before leaving for our trip. Not spending any time at what was...
    Reviewed 7 August 2018
    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
    Large Modernized Home a Short Walk to Beach1 / 23
    (3)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Children's Pool
    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Myself an my family stayed for a week the house was beautiful nice an clean fully equipped with everything you need
    Reviewed 10 July 2019
    Stayed here for 1 week with 12 people (6 adults, 6 kids)PROS: great location which is 5 blocks to Shell Beach, nice sized pool, spa with screen, covered outdoor area great for...
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    About this property
    Quiet and serene, but close to local attractions, you will love this large 4 bedroom, family friendly home with 2 kitchens, new appliance and modern furnishings! Separate living areas can accommodate one large family or two smaller ones. Each living area has its own living room, kitchen, 2...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    The Treehouse1 / 35
    (1)Terrible
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the relaxed vibe of Siesta Key! The beautiful white sand beaches that make Siesta Key the #1 beach in the US are not even a five-minute stroll away. Siesta Key Village and the famous 3 miles of the softest 99.9% quartz sand beaches draws thousands to enjoy the island life. This two...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Big Pass Hideaway! A three bedroom two bath private home with large lap pool located just a short walk to Shell Beach is ready to accommodate you and your guests on your Siesta Key visit. Lush tropical plants and trees envelop the nearly 2,200 square foot home with expansive living...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Cape Aqua1 / 30
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located on the closest private street to America's #1 named.The two large double doors with decorative frosted glass welcome you into this spacious home. The floor plan offers a very...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    NEW POOL! 3 Bed 2 Bath on Siesta Key   Walk to beach   POOL  Great location1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 February 2019
    I loved that we were just a 2 block walk from the beach, less than a block from Siesta Key Village filled with restaurants, bars, grocery store, etc. Everyone in the Village was...
    Reviewed 23 March 2017
    This three bedroom two bath house is located on Siesta Key near the South Bridge. It has great beach access near several fun restaurants. The owners were very supportive and...
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    About this property
    SIESTA SUN VILLAS - BRAND NEW POOL! 3 Bed 2 bath home on Siesta Key in Sarasota, FL Sleeps 6 people in beds. We are on the beautiful Island of Siesta Key. Walking distance to the number 1 beach in the USA. Full kitchen with oven, microwave, fridge, freezer, coffee maker & toaster. Large HDTV in...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Our Beach House1 / 34
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 6 November 2018
    Nice place on Siesta Key. Little smaller than some previous places we’ve rented. Everything clean and comfortable. Pool and grill in back was great. Kitchen was fine with...
    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...
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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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    The Banyan - A Tropical Retreat in Paradise1 / 25
    (3)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 19 April 2019
    We loved this house and it was stocked with all the amenities that any renter will need for the beach. We especially loved the screened in porch and the cosy set-up of the house.
    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...
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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
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spread out and enjoy this wonderfully appointed and tastefully decorated 3/2 home with private pool just steps away from powder white sands of Siesta Key Beach. Not far from Siesta Key village too where you can eat out in one of the many restaurants, have a drink and dance the night away, grab a...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy a stress free vacation at this island paradise three bedroom two bath private home with heated pool. The property has recently been renovated and finished with all new furniture throughout. Pulling up to this private home via the circular drive you will be greeted by its Key West...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach1 / 23
    (7)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
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    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2019
    Amazing. It's so close to the beautiful beach - just a short stroll across the road and a 10/15min walk to the village shops/restaurants. The property was clean, spacious and...
    Reviewed 23 April 2019
    This beautiful house is just the ticket for a large group. The location is within walking distance of the beach and village. It has a nice sized pool and the porch overlooking...
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    About this property
    This Luxury Four Bedroom plus den with a sleeper sofa bed has Four and a Half Bathrooms and will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach1 / 42
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2019
    From the magazine worthy interior decor to the outside oasis this home is a gem. We truly loved our stay at your Siesta home. The sunshine spills inside to brighten all the...
    Reviewed 12 August 2017
    I travelled to Florida with my fiancee for work and decided to extend our stay to enjoy a little R & R. We have used AirB&B in the past and we found this gorgeous home to...
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    About this property
    Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace, feed the ducks in the lake in our backyard or enjoy a dip in the...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Lovely Siesta Key & Sarasota 3 bedroom home - Less than 3 miles to Siesta Key1 / 23
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
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    • Private Garden
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2018
    There couldn't be a better house or location to stay at! It's only a short 10 minute drive from Turtle Beach and Siesta Key Beach and dead in the middle of everything that you'd...
    Reviewed 6 July 2017
    Perfect location for SIESTA KEY and THE Greater SARASOTA area. Shopping Centers, Restaurants , and The Beach are nearby. The Home is Great and Modern . Perfect for Families...
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    About this property
    From the beautifully landscaped front yard with the unique Rainbow Eucalyptus Tree to the spacious living areas, and the fantastic layout. As you enter this home, you will be impressed with the lovely touches this home has. It is tastefully updated, with recently installed new laminate floors, new...
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    Siesta Key, Florida 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    2 Bedrooms, 2 Bathrooms, Private Suites Sleeps 6. Ocean views on private lanai. Relax with your morning coffee with beautiful white sand and ocean breeze, so peaceful. Condo complex is right on the beautiful white sands of the #1 beach in the USA. So convenient, walk right out and put your toes in...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Retreat to this very spacious vacation home located on and overlooking the beautiful scenery of Philippi Creek, and only minutes from all the Siesta Key beaches. Relax with plenty of space through this large two bedroom and one and half bathroom home. Located in a quiet neighborhood with a great...
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    Siesta Key, Florida 34231
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury Condo Ground Floor Across the Street1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 9 June 2018
    This condo was perfect. It had everything we needed to feel right at home. It was clean and well-maintained and the owner was very responsive. Beaches were within walking...
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    Location! Location! Location! Walk out the door, across the street and onto the # 1 ranked beaches in America! This beautiful condo is on the ground floor, no steps, with a tropical enclosed lanai. It features 3 televisions, Tommy Bahama furnishings, a barbecue grill and high speed internet for...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    About this property
    Location, Location, Location! This 3 bedroom modern home with swimming pool is in the perfect location being less than a 5 minute walk from the soft white sands of the #1 Siesta Beach and only a 10 minute walk from all the shops and restaurants of Siesta Village. Located on a quiet street grants...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    The Henry1 / 47
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Reviewed 30 May 2019
    Have you ever been to a place that just feels right? A place where you don’t want to leave and can’t wait to come back again on Siesta Beach? A place where you dream of going...
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    The Property Live your travel lifestyle in the luxury stylings of The Henry. This one of a kind private accommodation on Siesta Key, features immaculate hand-picked designer furnishings staged to maximize the comfort, utility, and aesthetic appeal of each living space. From playing cards in the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Hot Tub
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    About this property
    Ocean Beach Gleason home rests on Siesta Key near Siesta Key Beach and Siesta Key Village. This is a stunning 4 bedroom or 3 br w/den, 2 bath updated and custom home all on one level with a saltwater pool (heat optional) and spa that over looks a small lake. Bring your well-behaved Fido with...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Looking for a custom home on the Canal with a private boat dock, where you can enjoy an amazing sunset every night?!....walk to Siesta Key Beach?!...., swim in your own private pool?!....be able to bring the whole gang?!.... desire serenity, peace, quiet!?......It's all here waiting for you on...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    There's a little piece of heaven nestled into a quiet neighborhood on Siesta Key ready for you......a stunning 4 bedroom, 3 bath home we call Siesta Isles. It's a spectacular pool home on Siesta Key just a short bike ride or a 15 minute walk to famous, #1 rated Siesta Key Beach & Pavilion with...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    If you are looking for a private home on Siesta Key that's only 460 feet from the Siesta Key Beach Access; then this is your vacation home to come to! It rests on a quiet street in a beautiful upscale neighborhood on Siesta Key just steps from playing in the sand with your kids, or reading a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Gated, 3b/2b Single Family Oasis 1 Block to Siesta Village 3 Beds/2 Baths, Sleeps 8 Welcome to your oasis on Peaceable in the exclusive Treasure Boat community, only 1 block from Siesta Key Village. This beautiful and updated 3 bedroom pool home with 2 baths sits on a private lot and includes an...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *** NEW *** Looking for that perfect location on Siesta Key? Look no further than this beautifully updated home and enjoy the relaxed vibe of Siesta Key! The famous 3 miles of the softest 99.9% quartz sand beaches draws thousands to enjoy the island life. These beautiful white sand beaches that...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Smoking allowed
    About this property
    This is spacious house, located in Monterey Street, close to downtown and beaches. With 3 bedrooms, 2.5 bathrooms, a private swimming pool, equipped kitchen and TV equipped living room, it can perfectly accommodate a family or group of friends of 6 guests. The house is located in a residential area...
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    Siesta Key, Florida 34231
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Reside at this elegant retreat for your extended stay on beautiful Siesta Key. Enjoy the islands' miles of #1 rated beaches and laidback lifestyle of Siesta Key Village within walking distance or a quick bike ride. This single story 4 bedroom 3 1/2 bathroom canal front home features a large...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Key has grown in popularity over the years as a vacation hot spot. This is due not only to the islands' beautiful beaches but diving into that 'island lifestyle'. What better way to take advantage of both then to stay at a property just a couple blocks from Siesta Key village and less than...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Welcome to the Oxford house on the barrier island of Siesta Key. Tucked away in the center of the island in one of the only lush tropical wooded areas on the island, resides this recently updated home. Siesta Key has become popular over the years for its beautiful beaches and island villages....
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Get the best of both locations with this beach property. Located across the street with direct access to Siesta Key beach and just a few blocks from Siesta Key Village. Enter through the front door and step into the large living area of this beach cottage. Bright and sunny seating area, living...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Key is a popular island destination voted #1 for its beaches and top 5 places to live numerous times by Dr. Beach, TripAdvisor, and USnews. The home is located towards the north end of SIesta Key affording guests a prime location for quick access on and off the island. Siesta Key Village,...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DIRECTLY ON NUMBER ONE RATED BEACH IN THE USA SIESTA BEACH!!! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Beachfront home on Siesta Key Sunset Point. Siesta Key Beach is the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a look at this spacious canal front home on Siesta Key with heated pool. This home is great for a large family or even two families with its open floor plan. Enter the home through the double French doors and down the foyer into the heart of the home; the open family room, living room w/...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay at this large Key West style Siesta Key vacation rental home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool and Jacuzzi hot tub. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Siesta Sunsets Treat yourself to an exquisite getaway at this Sarasota condo, part of the high-end Harbor Towers Yacht & Racquet Club. Boasting a variety of upscale community amenities - including three lighted Har-Tru tennis courts, an on-site fitness center, a pool and hot tub, and an unbeatable...
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    Siesta Key, Florida 34239
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    About this property
    This single-family home offers three bedrooms and three bathrooms; no need to share here! Two of these are large suites with brand new bathrooms, one with a king-size bed and one with a queen-size bed. The main living area is open from the living room to the dinning room to the kitchen giving this...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Terrace
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    About this property
    Peppertree Perfection *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. This second-floor condo offers privacy, seclusion, a view of the bay, and a host of other great amenities. You will enjoy...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    lovely house in the private yard.The deck is covered by a lanai and is surrounded by tropical plants including key lime, coconut, and banana giving complete privacy, the pool enjoys the sun all day, shady areas can be sought on the large deck. There is a full sized double garage and driveway...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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