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Holiday Rentals with Pools in Anna Maria Island

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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday home today, and have the perfect trip.
    482 Matching Rentals in Anna Maria IslandView all 939 rentals
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    Ocean View 3 bedroom, pool, North Shore Drive1 / 123
    (38)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches1 / 31
    (10)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    A Pearl of a Beach Home - with luxury private heated pool and hot tub1 / 36
    (38)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Absolutely Perfect - Cove at Sandy Pointe #2071 / 21
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2019
    Lovely airy apartment. 5 minute walk to Publix and the island hopper bus stop, about 10 minutes walk to the beach. Lots of beach accessories provided.
    Reviewed 14 February 2019
    Lovely apartment,clean, well appointed, like being at home, I hope it's available next year! Next to all amenities.
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    About this property
    Very contemporary condo (danish style), just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise. The unit is inspiring and gives you a laid back feeling immediately after entering. A huge pool with lounges and sun...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Waterfront and dog-friendly home with private pool, dock, views, and lanai!1 / 29
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Washer
    • Private Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anna Maria's Finest Spacious and sophisticated, this waterfront and dog-friendly Anna Maria Island home puts the best of everything at your fingertips. Featuring a private dock, pool, and amazing water views, you’ll experience the luxurious side of Anna Maria Island paradise during your stay....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    The Anna Maria Island Beach Palms 5B1 / 81
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 May 2019
    We really enjoyed our stay at the condo, it was a great location. So great to be on the inlet side and then take a very short walk to get to the beach. Everything was updated...
    Reviewed 20 June 2018
    We loved our stay in this condo and Anna Maria Island! Terry was a great help and always quick to respond. He provided a lot of helpful tips and information. We loved how...
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    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach. The Anna Maria Island Beach Palms 5B is completely surrounded by water and has just been completely...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Charming house with private heated pool, patio, and grill - steps from beach1 / 37
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2018
    Very spacious and open layout- Great for my parents as the use walkers. Master bath was perfect with the walk in shower! It was nice having space enough to be able to be...
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    About this property
    Pretty Palms Align yourself to island time with this cozy and colorful Anna Maria cottage! With a heated pool, shallow tanning area, and a lush tropical oasis right out back, any post-flight crankiness will melt right away. A stunning Anna Maria sunset completes your backyard paradise scene....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!1 / 50
    (13)Excellent
    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 24 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
    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 22 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
    Crescent Wave1 / 40
    (31)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Certificate of Excellence
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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 8 August 2019
    I never left a review, but our trip was so great i figured it was better late than never! We stayed at this house in Dec 2016 for our friends’ wedding on the island. (Month...
    Reviewed 8 August 2019
    The owner Richard was fantastic to work with. He answered all my questions and was very accommodating and got back to me in a timely manner. The house was clean and the beds...
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Coconuts Beach Front 106 Ground Floor1 / 21
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Waterfront
    • Washer
    • DVD Player
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2018
    This is a beautiful spot just steps from the beach and close to everything. Just be careful if you need full wheelchair accessibility for yourself or someone you are traveling...
    Reviewed 19 August 2015
    Right on the beach! Perfect view and immediate access to the warm Gulf water.Basic accomodation, nicely done recent upgrades to unit.Mentioned to office staff under bed dust...
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    About this property
    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability1 / 38
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 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 28 October 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Anna Maria Island Beach Sands1 / 99
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2018
    My family and I stayed at this condo and it was amazing. From the moment you walk in for the first time, you are taken back by the beauty this unit has to offer. Everything...
    Reviewed 16 April 2015
    This was our fifth year returning to AMI and this condo. Our condo is up to date, clean andvery well kept. The view from the balcony is breathtaking and are able to enjoy the...
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    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! The Anna Maria Island Beach Sands.' Just completely remodelled for your vacation comfort' -new designer kitchen -quartz counter tops -matching quartz backsplash -all new state of the art black graphite appliances -two...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Anna Maria Island Private Tropical Garden Home1 / 37
    (103)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2019
    We finally were able to get back to "our" island home - this was our 7th or 8th visit and we spent a week with family celebrating a few milestones and it was just...
    Reviewed 30 November 2018
    We were so happy to arrive to the island again and this time almost perfected the art of doing NOTHING for a week. This home is super spacious, clean and its location is ideal...
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Great Townhouse Very Close to the Beach, Shops, and Restaurants1 / 28
    (17)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
    • Patio
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2019
    Very nice condo, close to beach, quiet area. Furnishings very well maintained. Great that there were items to take to beach. Great if you are flying into the area and can't...
    Reviewed 14 May 2019
    We had a great time visiting Anna Maria for the first time. The home was nice and accommodated our needs for the week. The beach chairs, wagons, and extra towels were a plus...
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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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    Location Information
    Holmes Beach, Anna Maria Island 32417
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Sand Castle well appointed home steps from beaches1 / 25
    (4)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 26 July 2019
    This is our second stay at this home. Could not be more pleased. Very clean and equipped with everything you could need.
    Reviewed 24 May 2019
    Sandcastles was perfect for the four of us. Anna Marie Island is a great place to stay, very relaxed with plenty of places to eat out, many golf courses near by and wonderful...
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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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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    The Anna Maria Island Beach Palms 7A1 / 89
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2019
    Close walk to the beach. Close walk to bars and restaurants. Rental included beach chairs and an umbrella - which turned out to be very useful. We enjoyed great weather...
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    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! The Anna Maria Island Beach Palms 7A has just been completely remodelled with all new flooring, all new contemporary doors, all new baseboards, completely repainted from wall to wall and much more..... See our upated...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 14531 / 27
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2018
    We fully enjoyed our week at Bradenton Beach. Bermuda Bay 1453 was wonderful and highly recommend staying when visiting the area. A great relaxing and quiet week of sunshine...
    Reviewed 26 August 2017
    We stayed here in August 2017 for 2 weeks and it is a perfect location. The condo is spacious, bright, airy and spotlessly clean. The beach is just steps away across the road...
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    About this property
    Anna Maria Island boasts one of the longest stretches of sugar white beaches in Florida, and clear, aqua-marine water. Enjoy the natural setting from this spectacular townhouse on Bradenton Beach. This three bedroom, two-and-a-half bath home offers direct Gulf views, a king size master suite,...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    The Anna Maria Island Beach Sands 2011 / 61
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 November 2017
    We stayed here for nearly three weeks. Communication with the owner was excellent and helpful. The apartment was excellent, very comfortable, clean and well equipped. The...
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    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! Surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. We have the best location on Anna Maria Island where the island is only...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Runaway Bay 248 - Across the street from the beach - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. Community pool. Runaway Bay ----Large complex ---right across the street from the beach. Easy beach access. Come and relax on Anna Maria Island, the best kept secret in Florida! We...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Absolute Anna Maria1 / 100
    (21)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2019
    This was our 3rd year staying at this condo. Terry and Sandy are very nice and check regularly to ask if everything is ok and if we need anything. Condo is clean, kitchen is...
    Reviewed 22 March 2016
    Had condo 101 which faced directly onto the sea, lovely condo decorated with seaside colors, hundreds of towels and everything you could need, we had a great vacation Anna Marie...
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    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! Absolute Anna Maria is completely surrounded by water with the Gulf of Mexico to the west, Florida's Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. Absolute Anna Maria offers...
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    Location Information
    Anna Maria Island, Florida 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    'Elegance' 100 Steps from the Beach!1 / 48
    (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 16 April 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 2 November 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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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Patio
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Heavenly Holly Bask in the endless sunshine of Anna Maria Island at this three-bedroom home, a Florida escape with a private canalfront dock, its very own heated pool and a wondrous location only two blocks from the beach. This sleek, light-filled home is located on the quiet North End of Anna...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Coconuts Two Bedroom 118 Upstairs Courtyard1 / 23
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Internet Access
    • Parking
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2018
    Could have been cleaner.Beds in guest bedroom need to be replaced.Every time you turned, sounded like bed would collapse. Mattress in both beds old. Needs updating
    Reviewed 11 November 2017
    Would highly recommend... the condo was perfect for our family. Master bath and kitchen had both been recently renovated- gorgeous! The pool was heated and was fun to swim in...
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    About this property
    Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 6 to...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    The Anna Maria Island Beach Castle1 / 53
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 April 2019
    Excellent location walking distance to restaurants beach. Some of the most beautiful sunsets I’ve ever seen
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    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! The Beach Castle is located with-in walking distance of Anna Maria Island's best waterfront restaurants, beach shops, gift shops, shell shops, boutiques and the quaint shopping village on Bridge St. that leads right out...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Bradenton Beach Club A1 / 46
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2014
    This condo was ideally located and had excellent views. Description and views were represented accurately. Very spacious, accomadated our crew and guests well. Be advised the...
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    About this property
    Bradenton Beach Club A - Condo 3 Bedroom/ 2 Bath ocean view, maximum occupancy of 6 people. 2 Community pools (1 gulf front) Luxury Gulf front 3 bedroom, 2 bath condo with gulf side pool and elevator. Professionally decorated with a tropical flair. Enjoy great views of the gulf from your lanai...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach. The Anna Maria Island 'Beach Paradise 6 is located on Holmes Beach directly in the middle of Anna Maria...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Coconuts Poolside Unit 1041 / 22
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2016
    Awesome, already booked this for next year! Easy to fond, easy to get to beach, great people to work with.
    Reviewed 19 January 2016
    We were there in January 2016 and we were very happy with the accommodations. The decor is a little dated but all the essentials were there. We enjoyed Holmes Beach and...
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    About this property
    One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! Surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. We have the best location on Anna Maria Island where the island is only...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Terrace
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    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright and light condo on the second floor with view to the Palma Sola Bay (left side) and a peek-a-boo-view to the beach (right side) but only some steps away from the blue green water of the Gulf. 7 miles of white sandy beaches invite you for walking, swimming or only relaxing and enjoying the...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sundance Cottage Pack your flip flops and sunscreen and come stay in this beautiful three-bedroom house in Anna Maria ideally located within walking distance to the beach, dining, and more. With a private pool and a classic Florida atmosphere, your days will be a little brighter here. You'll be...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Pineapple Cottage You're sure to fall in love with this charming, dog-friendly Anna Maria cottage! Enjoy a fantastic location, beautiful beaches, and perks like a private heated pool. You, your loved ones, and dogs under 25 pounds (for a small nightly fee) will adore this home on Spring Avenue....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    **PARADISE RETREAT IN BRADEN RIVER LAKES**1 / 23
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 January 2019
    I stayed at this property Novemeber 18-20. I was there to enjoy some of the theme parks in close proximity and even was able to go to the beach! Rhonda was a great host and made...
    Reviewed 29 May 2018
    We really enjoyed our stay for Memorial Day weekend. Even though the weather wasn't what we planned for, thanks to a tropical storm! Of course the first one of the season and...
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    About this property
    This tropical retreat single family home boasts 1800sq. ft.of living space on the in the Braden River Lakes subdivision. The home is nestled among lush tropical palms and Florida vegetation. The expansive plantings provide privacy and a natural preserve setting in the backyard tropical paradise....
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    Location Information
    Bradenton Beach, Anna Maria Island 34208
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Bermuda Bay is a beautiful Gulf to Bay property that is located 1/2 block away from the beautiful beaches offering you all of the conveniences you would want in an island stay. The complex has a large heated pool and spa, from the pool you can stroll down the boardwalk to the bay where you can take...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Blue Bayou You'll fall in love with the island life in no time when you stay at this canal front Anna Maria vacation rental! Platinum-rated and featuring a private pool, private spa, and three parking spots, this home features all the amenities you need for a relaxing Florida beach vacation....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Mangrove Cottage Come live the island life when you stay in this charming 'Old Florida' style cottage with a private saltwater pool and close proximity to the beach. You'll also have room for three cars in the roomy carport and access to Anna Maria's free trolley. With only one house between...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Minutes to private beach access ! Newly Updated Beach Condo !  Pool, WiFi, Gri1 / 35
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 January 2019
    It was misleading right away when it advertised as being a bungalow. This is an apartment. We drove up and were instantly shocked and amused. We didn't find the pool. Nights...
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    About this property
    Minutes to the beach , this updated coastal beach condo is all you need for a stay in paradise. Beach living without the price tag. Bradenton beach is centrally located just south of Anna Maria, just north of Longboat Key and Sarasota beaches. Jump on the free trolley and explore the eclectic feel...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Bay Watch Bungalow: Water Views from Every Room & Upgrades Galore You’ve found a true treasure at Bay Watch Bungalow on Anna Maria Island! This 2-bedroom, 2-bath condo offers cottage-chic style and family-friendly amenities just 100 yards from the beach. Even better? The entire condo has been...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Welcome to The Sea Hag! Beachy , colorful sun worn on the outside... cozy, serene, cool and airy on the inside! This newly renovated condo , is situated 5 minutes from the beach on a protected park providing privacy for your outdoor patio. Free trolley , tennis , shuffleboard, basketball courts...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. We have the best location on Anna Maria Island where the island is only 150 yards wide. Our complex stretches from the Gulf to the Intra-Coastal...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    The Anna Maria Island Beach Paradise 51 / 62
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2015
    we loved Anna Maria Island, a great place to unwind after a week in Orlando. Beach Paradise was very centrally located, just across the road from the public beach and the free...
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    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! The Anna Maria Island Beach Paradise 5 condo is located directly in the middle of beautiful Anna Maria Island on Holmes Beach. This is a delightful location conveniently located across from the seven acre Manatee Public...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paradise Pointe Retreat to your very own garden oasis at this three-bedroom Anna Maria home, a waterfront escape with a private dock on the canal, an outdoor pool, and an enviable location mere blocks from Bean Point Beach. You'll find this home on the serene North End of Anna Maria Island,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM!!! The Anna Maria Island Beach View 208 is completely surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. Offering you the best location on Anna Maria Island where...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Dog-friendly duplex with two separate spaces, private pool, blocks to the beach!1 / 40
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    About this property
    Long Board and Short Board Book this elevated Anna Maria vacation duplex and you'll understand the feeling of love at first sunset. Consisting of both Long Board and Short Board rentals, this vacation option offers a private heated pool and a spacious Key West-style deck, plus, you can even bring...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! Surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. We have the best location on Anna Maria Island where the island is only...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Waterfront
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Emma's Cottage For your next Anna Maria Island adventure, enjoy a stunning, one-of-a-kind vacation destination. From an oceanfront location to a private pool and original antiques, you won’t another Florida home like this one! Built by Emma Palmer in 1912, this home is one of four Anna Maria...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    LARGE Key West style POOL HOME Private Tropical Paradise near beach! Anna Maria1 / 25
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2018
    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 20 September 2018
    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Coconuts Beach Front 109 Upstairs1 / 20
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Reviewed 1 May 2018
    Very pleased with the condo. Stayed in unit 109 on the first floor that had a fabulous outlook. New owners have gone to town and gutted the place with all modern furnishings...
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    About this property
    One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a fantastic location? It doesn't get better than this ! Feel the stress slip away as you enter this island oasis. Centrally located on the island, this 2 bedroom, 2 bath condo sits right across from the sparkling gulf waters of Holmes Beach . Uniquely situated just south of Anna Maria...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Looking for an island getaway without all the hassle? We’ve pretty much thought of everything, so you don’t have to.We have just updated the spacious master suite ! Whether you’re looking to relax or party it up — you found the right place. Located on Anna Maria island, best known for it’s...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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