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Holiday Rentals with Pools in Anna Maria

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    Travellers to Anna Maria are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    45 Matching Rentals in Anna MariaView all 182 rentals
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    Crescent Wave1 / 40
    (24)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    5 Star - Private Pool & Dock - May Availability - Special Pricing1 / 39
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Gorgeous views,spectacular home!1 / 92
    (30)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Anna Maria Island Nantucket1 / 58
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2018
    My extended family stayed here this past December, and it was perfect. The place is showing it's age a bit, and there is a rather steep set of stairs to get to the main floor...
    Reviewed 11 April 2017
    We rented this home over Spring Break with my brother and his family. The layout of this house is great as well as the location of the home on the island. There were 2 master...
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    About this property
    3 Story 'Nantucket' Style - 4 bedroom/ 3 bath villa is just a short walk to the beach - Nestled in a tropical setting, only a few blocks to the Gulf beach; heated private pool great for cooling off and a large sun deck. 4 Bedrooms/3 baths, large master suite with king size bed and a roman tub,...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    209 Spring - Private home 3 Bedroom / 2 Bath with private pool, maximum occupancy of 8 people. Distance to the Beach: 1 Block Spring into the waves!~ 209 Spring. 3 bedroom, 2 bath raised home in quiet, residential area of Anna Maria. Private pool. Pool heat optional * $20/day. 1 block to...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cast Villa 11 / 31
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2017
    Was absolutely wonderful. Couldn't ask for better vacation. Very close to beach. Unit had everything we needed. Owner was very friendly and accomidating. Will definately be back.
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    About this property
    Anna Maria Island, This property is located directly across from the famous Manatee County Public Beach. Groomed daily, Lifeguards, restaurants, surf shop and more.. Free trolley stops there both northbound and south every 20 minutes. The location is also right in the heart of the island. Walk to...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Blue Heron Waterfront House Anna Maria island1 / 23
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    We stayed for a week at the end of May 2017 after spending 10 days in Orlando. We were met at the property (even though we were a little late) and it was beautifully presented...
    Reviewed 23 May 2017
    The location is perfect. Walk 2 blocks to beach. Supermarket, drug store, bank, restaurants, salon, spa, less than 5 min. away. Many choices to dine/shop 3-10 min drive. The...
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    About this property
    Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make this home feel like you are...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    744 Jacaranda Rd1 / 64
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2013
    We loved this house for the week we spent in it. it was very clean and had all the little extras that make a holiday let in the U.S. ideal for a U.K. family - i.e. lots of beach...
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    About this property
    744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Distance to the Beach: 1 1/2 block Rates just reduced!! Book your holiday getaway today. $200 off any booking for the first two weeks in December 2018. Exclued the Holidays.(December 22, 2018 -January...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Anna Maria Island 'High End' Vacation Rental1 / 21
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    The location is perfect - walking distance from both the beach and the Pine Avenue shops. This is a beautiful 2 bedroom home, outfitted with every detail. The pool and hot tub...
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    About this property
    The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Americans and houses the bar and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sand Castle well appointed home steps from beaches1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2017
    My family stayed in this home August 2016. The home is beautiful and we enjoyed our stay very much. The home was well equipped and pretty clean. I did has a couple issues at...
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    About this property
    Beautiful, recently renovated 1700 sf home that accommodates up to 8 people. Only a few steps to amazing sandy gulf beach. Enjoy all the amenities of a single level well appointed home with no stairs where you can step out to the beautifully landscaped pool area from your master bedroom or open...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Dolphin Pointe1 / 39
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
    • Washer
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 2017
    My sister and 2 friends came here for 6 days. The house was perfect, the weather was cool and windy the 1st couple of days, but with the pool being secluded, we got to hang out...
    Reviewed 30 January 2017
    The house is just as the pictures suggests. The floor plan was very spacious. We traveled with 6 adults (4 were college students) and there was ample room to spread out. The...
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    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. The home exudes an Island charm...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. Distance to the Beach: 5 long blocks This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear,...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Ocean View 3 bedroom, pool, North Shore Drive1 / 246
    (36)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2017
    Great place I had my birthday party here it was so fun Very close to the water every thing was to the t in cleanliness sleep 6 of us it was all around one of the best beach...
    Reviewed 30 July 2017
    We love this beach house! It has everything, is always clean, great location, and the owner is the nicest to deal with! We will definitely be back...if someone else doesn't book...
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    About this property
    Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    AMI Coastal Retreats- 'Island Oasis'1 / 42
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The location is amazing for boats/jet skis. The house is perfect for up to two families with two master suites and an additional half bath. The kitchen is well-equipped with...
    Reviewed 1 October 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
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    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • DVD Player
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beachy Keen 408 - Private home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. Distance to the Beach: 1 1/2 block Here delightful and fun Caribbean Cool décor welcomes you to the sub tropic cozy of Anna Maria Island. A charming island home within easy walking distance to the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    103 Pelican1 / 14
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Balcony
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2016
    Hi! My husband and I rented this property and had the wonderful opportunity of having our adult children & their spouses come with us. There was 8 of us in total. We...
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    About this property
    103 Pelican - Private canal home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. At this spacious, family friendly home with private pool, grab your fishing pole, take the hand of a child and meander to the private dock, cast a line while dangling your feet and spending the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cast Villa #4 is the most private on this lush tropical Half acre property. Located directly across from the famous Manatee County Pubic Beach. Swim with Life guards present. Known for the pristine sugar white sand beaches. Dine early breakfast or have a beverage listening to live music daily....
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Discount July 4th week! Pool, Hottub,Fish, Dock, Kayak* Steps to Gulfside beach!1 / 23
    (13)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2018
    My family and I had a wonderful stay at Beach Nest. Liza was more than accommodating. We had to cancel due to unforeseen reasons and she allowed us to pick from a number of...
    Reviewed 25 February 2017
    Beach Nest is wonderful. Decorated with flair and beachy elegance, it feels like a home, not a rental. There is everything you need and more. You can walk to the beach with your...
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    About this property
    Water lovers too! Ahhhh-Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! Vacationers, dreamers, honeymooners, would-be family-reunion...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Anna Maria's Coconut Breeze Estate - no cleaning fee1 / 49
    (5)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2017
    Really beautiful home and close to everything. Huge place. 2 minute walk from Rod and Reel Pier and 5 minutes to Bean Point (though wouldn't recommend swimming there, current...
    Reviewed 10 May 2017
    This home really does have the "wow factor." The moment we walked through the door we were blown away. The best of everything is in this home...the kitchen appliances...
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    About this property
    This beautiful gem in the much coveted City of Anna Maria's north end. It is a single family home located on a quite street. Easy walk to the gorgeous white sand Bay and sugary sand Gulf of Mexico beaches with striking sunsets . With Pine Ave (our fantastic little Main St.) just a short stroll from...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ibis unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come discover 'Paradise Cottage' with all it's old Florida charm as well as newly updated appliances and decor.  This lovely and colorful two bedroom, two bath home feels brand new.  You'll enjoy tile floors throughout, a large eat-in kichen, comfortable and attractive furnishings with an updated...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 bed luxury upscale executive waterfront home1 / 50
    (10)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 February 2017
    Bayview Dream did not disappoint! It truly was a dream holiday for us. The house itself is beautifully decorated and very well equipped - plenty of towels (indoor and pool...
    Reviewed 17 January 2016
    We spent a week in this lovely home. The weather was cool, so we didn't use the pool, but there was a beautiful pool with a dock right out the back door. The home was spacious...
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    About this property
    Location, Location, Location. Upscale luxury executive four bedroom waterfront home with private pool dock and elevator. Stylishly furnished and dressed, modern build 2006 - this is our family second home - and is home from home available to you. This exclusive executive property is in the...
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    Location Information
    Anna Maria, Anna Maria Island FL34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Beach to Bay Getaway! Anna Maria Island was a quaint historic fishing village and has become one of the top travel destinations by travelers from around the world. Known for world class beaches, top rated restaurants, fishing/boating and laid back stmosphere. This...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Grill
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The desirable North end of Anna Maria and a peaceful canal front setting make this beautiful home a perfect vacation getaway! Gladiolus on the Water was recently updated with new furnishings and fresh paint, all tied together with a festive and tropical theme! With a comfortable couch and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
    • Washer
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled right in the midst of Anna Maria Island is this 3 bedroom 2 bath single family home with private pool. The pool area is very inviting with sun on it throughout the day... Enjoy evening cocktails in the large screened in poolside patio. Enjoy a hot outside shower when you get home from the...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Patio
    • Private Outdoor Pool (Unheated)
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    • Terrace
    • Hot Tub
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tarpon Pointe is a gorgeous newly remodeled 2 bedroom 2 bath island home located on the north end of Anna Maria Island. You’ll enter the home from a large front deck with sliding glass doors into the living area. The living area features a large 65 flat screen HDTV with plenty of seating for the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Air Conditioning
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill for an evening of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Terrace
    • Balcony
    • Shared Outdoor Pool (Unheated)
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New Rental!   Sea Haze is a mere 212 steps to the beach and the crystalline gulf! As you take your short walk to the gulf beaches, you will take in the sights of the dense banyans, spectacular homes of Park Avenue and the tropical sea grapes. Sea Haze is perfectly located - west of Gulf...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
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    • Private Outdoor Pool (Unheated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Deja Vu is just a short stroll to the beautiful beaches of Anna Maria!  This gorgeous home is a 3 bedroom 3 bath with a private heated pool. The pool area is very inviting with the sun on it throughout the day.  After a long day at the beautiful beaches of Anna Maria freshen up with the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
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    • Private Outdoor Pool (Unheated)
    • Terrace
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Manatee Cottage is a newly remodeled two bedroom, two bathroom private home with a pool and spa. This fabulous house is only a short walk to the white sand beaches of Anna Maria and also a short walk to Bay Front park.  Stroll down to Pine Avenue and dine out at one of the many fine...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Parking
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lime in De Coconut - Upstairs..... Adorable, one bedroom, one bath in a 2 unit cottage. Cheery beach decor and a shared heated pool in a tropically landscaped courtyard. Flat screen TV, wireless internet access, washer & dryer, and a gas grill (propane is guest's responsibility). Located just a...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7201 Palm Drive, Holmes Beach, Anna Maria Island Palm Cottage ... Lovely 2 bedroom, 2 bath recently updated home. This ground level home offers a beachy decor, a new pool , granite countertops, and a great screened in porch. Just a short walk to the beach. Pool heat is additional....
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Copacabana1 / 21
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 November 2017
    We have had a wonderful two week stay at Copacabana, it is a very well presented and comfortable holiday home, which has recently been modernised to a high standard throughout...
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    About this property
    Copacabana is newly remodeled 3 bedroom, 2 bath private home that sits right on the canal in Anna Maria in a very quiet neighborhood. There is now a brand new kitchen for entertaining and new tile floors flow throughout and with a designer’s stylish touch, you will feel you have found your home...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lime In De Coconut- Downstairs. Adorable, ground level two bedroom, two bath in a 2 unit cottage. Cheery beach decor and a shared heated pool in a tropically landscaped courtyard. This unit also offers a screened lanai, flat screen TVs, wireless internet access, washer & dryer, dishwasher and a gas...
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    Anna Maria, Anna Maria Island 34217
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Washer
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Bay is a gorgeous brand new, custom luxury home that is a the perfect rental home for your next vacation. This stunning high end home is comprised of two separate buildings, a main house and a guest house, with a tropical pool with tiki, spa, grill, sun deck and fire pit, in between the two....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Managed by an agency no direct bookings here. Located on beautiful Anna Maria Island, 'Le Paradis' (which means Paradise in French) is just a short stroll to the sugar white sand beaches of beautiful Anna Maria Island... Experience a luxurious beach vacation with over 2100 hundred square feet of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful gem of a home is located in the much coveted north end of Anna Maria Island in the City of Anna Maria. It is a single family home located on a quite street. Just a 2 minute walk to the gorgeous white sand beaches on the bay side of the island and about a 10 minute walk to the sugary...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Stunning luxury newly constructed beachfront villa1 / 22
    (22)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2017
    Beautiful three level beach house on the northern end of Anna Maria Island. Relaxing and very comfortable home where our family enjoyed reconnecting during our vacation after a...
    Reviewed 2 May 2017
    If you are looking for a property to relax by the beach or a swimming pool, this is about as good as it gets. There is nothing the owner's have not thought about. Great ocean...
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    About this property
    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Cherryfish, a spectacular spacious 4-bed home!1 / 29
    (9)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    • Balcony
    • Porch
    • Cable/satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 2017
    Cherryfish is the ultimate vacation home. We have vacationed in Anna Maria numerous times and have stayed at Cherryfish twice it is our favorite home and we will stay there...
    Reviewed 4 July 2017
    We've just come back from an amazing holiday staying at Cherryfish. I couldn't recommend it enough for a large family or two sharing.Cherryfish is a beautifully maintained...
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    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Secure Parking
    • Cable/satellite TV
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated beach condo just 50 steps to the sand. Over 1200 sq ft with 2 lanais and 1 spacious rooftop deck for spectacular ocean views. Granite Counter Tops Stainless Steel Appliances Washer and Dryer Heated Outdoor Pool Beach Supplies Walking distance to restaurants and Shops Close to...
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    Anna Maria, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the sandy shores of Anna Maria at ‘Easy Breezy’, a recently renovated canalfront vacation rental cottage only a short stroll from the beach! ‘Easy Breezy’ accommodates 6 guests with 2 beautiful bedrooms, 2 en-suite bathrooms, and a cozy sleeper sofa. Soak up the sun by the private pool...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    OakView - Anna Maria Island - Old World Florida1 / 22
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2015
    This house was beautiful and is well situated on the island. The yard and pool area are nicely landscaped, and it’s a short ½ block walk up a dead end street to get to the...
    Reviewed 13 January 2014
    The house was excellent and had everything that was expected. The walk to the beach was only about 500 ft. The pool was very nice and easy to clean up with the tools supplied...
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    About this property
    We completed construction of this new home is November 2009. It is a decorator furnished, pool home and is a top of the line vacation rental home. With approximately 3200 square feet of conditioned space and over 2100 square feet of covered balconies, poolside dining and lounging areas there is...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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