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Anna Maria Island House Rentals

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    Travelers to Anna Maria Island are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    739 Matching Rentals in Anna Maria IslandView all 1,326 rentals
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    Ohana Hale North  2  Bedroom on Anna Maria1 / 17
    (23)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gorgeous views,spectacular home!1 / 46
    (33)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    A Pearl of a Beach Home - with luxury private heated pool and hot tub1 / 32
    (29)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Happy Island Cottage with heated private Pool1 / 52
    (31)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Just back from a lovely stay in Happy island cottage, Anna Maria Island. This was our first trip abroad with our 15 month old son. The owner, Alex, went out of his way to...
    Reviewed July 8, 2018
    Alex answered any question i had. the house was everthing it was suppose to be.it was an amazing vacation.
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    About this property
    A brand NEW 2300 sq/ft, 3 bedroom modern beach house with heated and very private pool. A perfect location just steps from the beach, marina and the main plaza with great shops, a grocery store and restaurants. No need to drive anywhere. Located in a quiet neighborhood with tropical greenery, large...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. Distance to the Beach: 50 yards This well appointed home has recently been renovated. The balconies have all been redone, new stairway and all new furniture in the living room and bedrooms The master bedroom...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Playa West  is a Luxury 4 bedroom home with a pool and elevator!1 / 37
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Washer
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home provides you with your own private pool. It has virtually EVERYTHING you need for a perfect Island vacation. This home has a private pool and is less than a block to the beach and 1 block to Sarasota Bay for fishing. Walk to Sarasote Bay and watch the big yachts and boats pass by on the...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Ohana Hale South   West Suite1 / 24
    (33)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 2018
    Ohana Hale South - West SuiteWe found that the accommodation accurately matched the posted description and photos. Excellent communications from renter - very fast responses...
    Reviewed November 28, 2017
    My family came to visit me every year and I always booked Ohana beach condo. Everything is perfect here: the beach is across the street, the unit is very clean and beautiful...
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    About this property
    Aloha and welcome to our Island Home. Ohana is Hawaiian for family and that is who you are when you stay with us. Our retreat is nestled on Anna Maria Island, Florida and is a short 5 minute walk to the white sand beaches and turquoise waters of the Gulf of Mexico. Your vacation Hale (home) has...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    'Elegance' 100 Steps from the Beach!1 / 24
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 16, 2018
    We all really enjoyed our stay at Elegance villa, pool was amazing, location was excellent and Shawna was very helpful. We hope to visit again soon.
    Reviewed November 2, 2017
    Just returned from 6 nights stay at this beautiful house. The house was just lovely- clean, well equipped and very comfortable. The provision of plenty clean towels including...
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    About this property
    An elegant beach-house that redefines the idea of island comfort, built with love and an extreme attention to detail. Every room of the house has a unique ambiance combining color, textures and accent lighting. The outdoor area is one of the most spacious on the island with a large heated free form...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property is unavailable but for limited time we're matching the rates at our newly remodeled 'Seaclusion' Tripadvisor listing 6528563. Check out our Low intro rates! Your search for most awesome vacation rental is over. Sleeps 4-5 persons in 2 bedrm en-suites We are in the most sought after...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability1 / 39
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
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    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    The house was gorgeous. Pretty and comfortable furnishings. Loved all the Anna Maria touches. Fantastic kitchen appliances - I wish my washing machine was so good! We all loved...
    Reviewed October 28, 2016
    We had a fantastic time exploring Anna Maria Island and coming home to such a fantastic place made the holiday even more special.
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    About this property
    It doesn't get much better than being right on the water, less than one block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Crescent Wave1 / 40
    (24)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 28, 2018
    This house had everything we needed! Very clean and the pool was a big hit with the kids. Richard was very friendly and easy to work with. From booking to checkout it was as...
    Reviewed May 27, 2018
    Our family had a fun and relaxing stay with plenty of space and convenient walks to the beach, shops and restaurants. There was a wi fi issue the first day, but Richard had it...
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    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Luxury 3BR/3BA, Private Heated Pool, Beach1 / 34
    (36)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 26, 2018
    We have traveled to Anna Maria numerous times, and this is the best house by far! The pool is the best part of the house! Very private, outside T.V., game room, 3 bedrooms with...
    Reviewed July 5, 2018
    We really enjoyed our stay for the week. The owners contacted us in advance to ensure we would have everything needed. We were impressed by how clean and updated it was. The...
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    About this property
    http://www.villachezshell.com Villa Chez Shell is a newly renovated Mediterranean beach home that offers a luxurious getaway. The highlight of this newly renovated 3 bedroom and 3 bathroom property is its tropical private backyard complete with a lagoon shaped pool and a soothing stone waterfall....
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Waterfront 'HideAway Gem' Fish from yard! View that never ends! Jacuzzi Shower!1 / 34
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Washer
    • Waterfront
    • Patio
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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2018
    This little gem had everything we needed for an amazing visit to AMI! perfect location, great amenities, very reasonable! We were within easy and effortless distance to the...
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    About this property
    This beautiful vacation rental features the best panoramic open bay views, from every room, on all of Anna Maria Island! Enjoy our huge 162 foot long yard along the Bay front! Our beautiful two bedroom, one bath (walk in shower), is a rare ground floor vacation rental. NO STEPS TO CLIMB. No one...
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    Anna Maria Island, Florida 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casa Playa East is a Luxury 4 bedroom home with a pool and elevator!1 / 33
    (2)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 15, 2017
    We booked our stay here for our family (6 adults, 2 kids) totally unfamiliar with Anna Maria Island, coming for a wedding at a nearby venue. We couldn't have been happier...
    Reviewed August 8, 2015
    We rent a home in Anna Maria every year. Hands down, for my active group, this is the best location. Two blocks from hopping Bridge Street. Beach access 1/2 block away. Bay...
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    About this property
    This Bradenton Beach vacation home provides you and your family or small group with your very own private swimming pool, and comes fully equipped with everything you need for a wonderful vacation on this beautiful barrier island. Your accommodations are less than 1/2 block from the beach and 1...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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 March 20, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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    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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    New! 'The Pelican' 50 seconds walk to beach! Beach cart, umbrella, chairs incl!1 / 28
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 5, 2018
    This condo was beautiful and everything we needed for our long weekend away!It was very clean and fresh and decorated beautifully.The kitchen was great and all the little...
    Reviewed September 17, 2017
    Staying at The Pelican was a fantastic experience from start to finish. The rental seemed freshly renovated and felt like our home away from home. We had access to everything we...
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    About this property
    Location, location, location! Less than a min stroll to beach! We have just invested in a total makeover to our single story elevated vacation rental. Upgrades incl; granite counters. New Italian tile & oak (Pergo) floors throughout. Solid cherry wood cabinets & new premium stainless appliances....
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    116 Maple Breeze1 / 24
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 2, 2015
    Wonderful location, The beach is at the end of Maple Ave, a quiet road only a 2 minute walk. The house is well situated, 4 bedrooms and 2 and 1/2 baths. I can only speak of...
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    About this property
    116 Maple Breeze Private home 4 Bedroom / 2 1/2 Bath , maximum occupancy of 7 people. Distance to the Beach: 200 Yards 116 Maples is located on one of the prettiest streets in the village of Anna Maria, this gorgeous 4 bedroom, 2 and a half bath home is just steps away from the beach. This...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Private Tropical Paradise in Holmes Beach!  Large home with Pool and fenced yard1 / 25
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Our family loves Anna Maria Island. This house is conveniently located within walking distance to beautiful beach. The house itself is fully stocked with everything we needed...
    Reviewed 4 weeks ago
    Location was great, in the middle of everything the island has to offer. Beautiful private beach just a few blocks away. We enjoyed the pool and the hot tub It was nice and...
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    About this property
    Tropical Paradise on Holmes Beach and ONLY 3 blocks to the beach. Anna Maria Island, noted for its old Florida ambiance, offers this Key West styled home, where you may awaken to greet the dawn sipping coffee on the balcony or swimming in your private pool. The modern interior arrangements add to...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Beach Front House - Shady Pines - Anna Maria Island,, FL.1 / 25
    (28)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 9, 2017
    My friends and I go to Shady Pines every year, it is a highlight for us. The house is perfect, steps to the beach to enjoy swimming in the Gulf, or walking the beach and...
    Reviewed October 8, 2017
    My wife and I stay at Shady Pines each year and it's the highlight of our year. It is an outstanding beach front property. We love it and look forward to it each year. There...
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    About this property
    Shady Pines is a tastefully decorated, 2 BR, 1-1/2 bath, beach house right on the beautiful Gulf of Mexico. Walk out the door to a wide, white, powdery beach and the Gulf. This 2 bedroom beach house is located in the most perfect spot you will ever find! Great views and privacy. This quiet beach...
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    Location Information
    Anna Maria Island, Florida 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    5801 DePalmas - Private home 3 Bedroom / 2 Bath , maximum occupancy of 6 people. Comfy and Cozy Florida Living!~ Distance to the Beach: 1/2 block Cute cozy ground level home 3 Bedroom/ 2Bath close to the beach on a quiet dead end street. Fully furnished with linens towels, cooking utensils,...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview Island Dream is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 3 bedrooms / 2 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the brand new (2018) luxurious heated pool and spa,...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stunning 5 bedroom Pool Home just steps from the beach!1 / 49
    (4)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    • Ocean Views
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 3, 2017
    This wonderful house is located about in the middle of the island, close to Walgreens (if you forgot something) and a couple of minutes from Publix (for your culinary needs...
    Reviewed March 3, 2013
    We had the most wonderful four days in this house with our baby son. The house is just two blocks from the beach and comes with basic gear (towels, umbrella, chairs, wagon...
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    About this property
    Beautiful 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway with everything you could want while enjoying Anna Maria Island. Just imagine waking up to the sound of the surf rolling in. Enjoy a cup of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Secure Parking
    • Cable/satellite TV
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    • Private Yard
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Many homes with a high bedrooms count sprung out on the island lately, designed to maximize rents, they are built on very small lots normally 50 ft wide and packed upwards in three levels . This is a well reviewed house that I built for me and my family in 1998, it is the largest private rental...
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    Location Information
    Anna Maria Island, Florida 34217
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    BEACHFRONT HOME, TRUE PARADISE , DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 22
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Washer
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    • Grill
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Six of us ladies had a great time and loved the house! Laura was very helpful. Hope we can do it again.
    Reviewed 2 weeks ago
    Very nice location, perfect if seeking a private and quiet location. All amenities necessary for us were included. Will return.
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    About this property
    This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the deck which runs the entire length of the home. The elevated deck is a mere 10' from the waters edge....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bay view Home, located at 404 21st Place in Bradenton Beach is a hidden treasure! This wonderful home features 4 bedrooms and 3 bathrooms on a quiet street ending at the water. Best of all, this beautiful home is canal front with beautiful views of the bay! It features a private heated pool, BBQ...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    19 Palms. Quaint Old-Florida Charm1 / 23
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 4, 2018
    My husband and I come to Anna Maria Island annually and always stay here. It’s spotless, beautifully decorated, ultra comfortable beds and new shower heads. The location...
    Reviewed March 4, 2018
    The location of the house is close to the beach and you can also walk to all the shops and dinning or bike ride. Parking is right at the doorstep and it is on a quiet street...
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    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Anna Maria Island Nantucket1 / 29
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • Washer
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 5, 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 April 10, 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    The Crow's Nest, located directly on the beach at 2416 Gulf Drive in Bradenton Beach is a unique three bedroom, two bath home that was designed by a man with a passion for boats and a love of the sea. From its lofty view, enjoy a perspective of Bradenton Beach from the spacious screened lanai that...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Anna Maria Great Townhouse, Great Value!1 / 28
    (14)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 23, 2018
    We've stayed at a number of places on Anna Maria Isl. and this beautiful house is one the best. You can see the new heated pool from the kids bedroom. Holmes Beach is only a 5-6...
    Reviewed August 7, 2017
    Tranquil and friendly people good beaches. Very family friendly,good neighbor Doddy, Very close to markets and restaurants.
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    About this property
    Grab your flip-flops and beach chairs! This family-friendly 3-bedroom, 2 1/2 -bath townhouse is just two quick blocks to the pristine, white sandy beaches of Anna Maria's gorgeous blue waters of the Gulf Coast. And after a relaxing day of sand and sun, come back for a refreshing dip in the heated...
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    Holmes Beach, Anna Maria Island 32417
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    BAY FRONT HOUSE WITH PRIVATE DOCK1 / 19
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Private Yard
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 2018
    House was in a good location right on the bay. Nice sitting area outside to watch the boats go by! The large Poinciana tree out back provided a ton of shade during the warm...
    Reviewed August 8, 2018
    House was perfect for the 2 of us plus 17 yoa son and dog. Walking distance to a couple of great restaurants and beach was about 2-3 min walk. Fished off the dock nearly every...
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    About this property
    Two Bedroom/2bath Home in Bradenton Beach Sleeps 6. This is a two bedroom/2bath home in Bradenton beach, with washer/dryer, new kitchen (granite counters), big screen/WiFi, great fishing on your own dock, on a quiet street, five minute walk to bridge street shopping area, two minute walk to the...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Playa - Combo1 / 52
    (3)Very good
    8 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Heated)
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    • DVD Player
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 27, 2015
    We stayed at Casa Playa for the week after Christmas over New Years! The location is amazing...close to everything you need except a grocery store. The weather was perfect, the...
    Reviewed April 9, 2014
    We stayed here for the full month of March and very much really liked this unit. The owners ( Scott Deb ) were very nice, as they were wanting to make sure we had everything we...
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    About this property
    This Bradenton Beach vacation home is actually two rentals in one, in the middle of all the fun and beaches that Bradenton Beach can offer. The rental package sleeps up to 20, and everyone can enjoy the 2 private swimming pools. This is a fully equipped rental home on Anna Maria Island, with...
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    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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    Charming 2 Bedroom/2 Bath Cottage on a Canal1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    • Hot Tub
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 2, 2018
    We thoroughly enjoyed our stay at this lovely cottage located on the northern tip of Anna Maria Island. The home is charming and well-cared for. The shaded yard was on the...
    Reviewed April 25, 2017
    I loved that the owner went our of her way to reserve pack and plays for our two little ones. They had everything for beach trips including a wagon, beach toys, and umbrellas...
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    About this property
    Our 2 bed/2 bath cottage is the perfect home to spend your vacation. Located on a canal, you can bring your boat or rent kayaks. Fishing is great from the dock. House and yard is very private. Soak in the jacuzzi after a long day at the beach or relax in the hammock. We have 2 bikes, beach...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    The Siboney located at 3700 Gulf Drive in Holmes Beach, is an exquisite, executive level home with a private heated pool set amidst tropical, native landscaping. Its 2000 square feet of luxury! The beach is approximately one half block away with no major roads to cross. You can enjoy views of the...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sandy Beach Access1 / 10
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sandy Beach Access Duplex, 2 bedrooms, 2 baths, 6 Places Newly renovated, fully furnished, 2 BR 2 Bath duplex. 202B 76th Street, Holmes Beach, FL 34217 New landscaping. 1 1/2 blocks (300 yards) to a beautiful sandy beach. Cable TV's, Wireless Internet, DVD Player. Laundry room. Anna Maria Island...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    The Anna Cabana Beach House is an adorable two bedroom, two bath home located at 3709 Gulf Drive in Holmes Beach. This quaint home has a large open deck with a great view of the beach. Watch the sunsets or enjoy the tropical landscaping on the large deck facing the Gulf. Numerous fruit trees and...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Escape to the Breakers, one of the finest luxury gulf front vacation homes on Anna Maria Island, located at 102 31st Street in Holmes Beach. Enjoy the tropical breezes and aqua-blue surf from the deck overlooking the white sand beach and sparkling Gulf of Mexico. Watch the dolphins cavort in the...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    744 Jacaranda Rd1 / 32
    (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 May 3, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Cast Away #1, located at 4101 Gulf Drive in Holmes Beach is a delightful condo situated conveniently across from the Manatee Public Beach and the shimmering Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Cast Away #2, located at 4101 Gulf Drive in Holmes Beach is a delightful condo situated conveniently across from the Manatee Public Beach and the shimmering Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    North Shore Villa Anna Maria1 / 27
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed September 14, 2016
    My family and I stayed with our friends and their children in late June 2016. We have teens and they have small children. This house is amazing! Its close to the water, you...
    Reviewed February 28, 2016
    This North Shore Villa is spacious, comfortable, and very clean. As close to the beach as you can be without being on the beach. The beach on the northern point of the island...
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    NORTH SHORE VILLA 904 North Shore Drive Anna Maria Welcome to North Shore Villa. This luxury Key West style home has it all. Expansive bay views, private heated pool, extra large master suite with a double shower and Jacuzzi tub, fresh and modern decor, two large balconies, indoor sitting area...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    About this property
    Cast Away located at 4101 Gulf Drive in Holmes Beach is a delightful condo situated conveniently across from the Manatee Public Beach and the shimmering Gulf of Mexico. These two bedroom and one bath units sleeps six each with a queen size bed, two twin beds and a sofa bed. A full size kitchen and...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lakeside Beach House is a wonderful newly renovated three bedroom, two bath home with a private and brand new heated pool. Located at 6935 Holmes Blvd. in Holmes Beach, this lovely property is convenient to the beach and in a very quiet, Holmes Beach residential neighborhood. This home faces...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    510 Bayview1 / 20
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    • Grill
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 29, 2016
    Had a fantastic week here nine adults and we did not bump into one another once 4double rooms and 1 twin all with their own bathrooms pool area great pity that the water...
    Reviewed December 29, 2015
    I recently stayed at this beautiful house and it was the best decision I made for the holiday. First, the rental company was so easy to work with. There was no stress at all...
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    About this property
    510 Bayview - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Island Elegance for the whole family!~ Distance to the Beach: 2 blocks Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and...
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    Holmes Beach, Anna Maria Island 34217
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Dolphin Pointe1 / 39
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
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    • Private Outdoor Pool (Heated)
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 10, 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 January 30, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Anna Maria Island Private Tropical Garden Home1 / 20
    (100)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Cable/satellite TV
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    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 20, 2018
    My family was celebrating Mom and Dad's 60th Anniversary and we wanted to do it up big. How lucky we were to discover this wonderful vacation home. The layout of the home was...
    Reviewed August 7, 2017
    Stayed here again in July 2017. We had just as much fun as we did the previous year. Kent and Pa take very good care of their home, and it is in perfect condition upon your...
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    About this property
    PRIVATE ISLAND PARADISE - This unique custom home is hidden on a huge garden lot surrounded by palms, birds of paradise, tropical plants and a 6 ft fence. Few island homes offer this degree of privacy. SPACIOUS ELEGANCE - The home has 2,600 sq ft (240 sq m.) of ground level indoor living space with...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Dolphin Dance North side, located at 803 Gulf Drive South is an impressive, two bedroom one and one half bath duplex with panoramic views of the Gulf of Mexico. This spacious, town home unit will sleep six with a queen size bed, a full size bed and a sofa bed. Extras include washer, dryer, VCR,...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Anna Cabana Bungalow #1 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a perfect complex for...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    The Sand Dollar, located at 143 50th Street in Holmes Beach is a beautiful, newly constructed four bedrooms, three and one half bath home with a large heated pool surrounded by native landscaping. It’s located on a quiet residential street west of Gulf Drive and less than a two minute walk to the...
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    Holmes Beach, Anna Maria Island 34218
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Sail Away Cottage is located at 2113 Avenue C in Bradenton Beach. This historic cottage was built in 1920 and moved to its current location in the 1980’s. It is only 170 steps to the sandy beaches and there is even a peek of the gulf! While the cottage still has the look and feel of the 1920’s,...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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