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Anna Maria Island Luxury Holiday Homes

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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    198 Matching Rentals in Anna Maria IslandView all 1,324 rentals
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This fun and convenient private home is a favorite amongst guests who return year after year! Located in the heart of Anna Maria Island, 'SURFSIDE' is close to all of the beach activities, shopping, dining, and entertainment. Amenities that set it apart include a LARGE, private fenced yard with...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    About this property
    At 4 bedrooms and 3 full bathrooms, this is one of the most charming rentals on Anna Maria Island!! Located a few houses from the beach, it is only a two minute walk until white powdery sand is between your toes! Easy on the kids and even easier on you! Around the corner from restaurants, pubs &...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    8 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This rental home on Anna Maria Island sleeps up to 20 and comes fully equipped. 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 private...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Secure Parking
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    • Private Garden
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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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    Anna Maria Island, Florida 34217
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Stunning luxury newly constructed beachfront villa1 / 22
    (22)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2017
    Beautiful three level beach house on the northern end of Anna Maria Island. Relaxing and very comfortable home where our family enjoyed reconnecting during our vacation after a...
    Reviewed 2 May 2017
    If you are looking for a property to relax by the beach or a swimming pool, this is about as good as it gets. There is nothing the owner's have not thought about. Great ocean...
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    About this property
    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Beautiful new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, stainless steel...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Jewel of the Bay: LUXURY Waterfront Home, Breathtaking Views! Pool,Spa,Elevator!1 / 24
    (6)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2018
    We have been renting this house in May for 3 years. It is awesome. Four king on suites so perfect for 4 couples. Beautifully appointed. Heated pool that overlooks your...
    Reviewed 6 June 2017
    Anna Maria is a wonderful place with a laid back way of life. There are some great places to eat and drink and the beaches are superb.The thing that made our holiday really...
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    About this property
    This is the luxury vacation rental home of your dreams! This custom bay-front home on the north end of Anna Maria Island offers 3600 square feet of luxury accommodations and has all the fine touches and professional craftsmanship one would expect in a high-end custom home. When walking into this...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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
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    • Private Outdoor Pool (Heated)
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    • Patio
    • DVD Player
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 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 10 April 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
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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    4 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 16
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    Limefish, spectacular beachfront location!1 / 22
    (30)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2015
    Just finished a 14 night stay at Limefish, and as 3 years ago it was a fantastic experience. As per the title the location is bang on, it's a 10 minute walk to the start of the...
    Reviewed 8 November 2014
    We were staying here with friends who were getting married on the beach. It is paradise. The villa was perfect for seven of us, though one couple had to have bunk beds, and we...
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    About this property
    Limefish, from Pineapplefish is one of the most stunning beachfront holiday rentals on Anna Maria Island, with direct access to a beautiful, almost private beach. With spectacular views across the Gulf, Limefish has a wonderful and spacious decked area across the whole of the property, where you...
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    Anna Maria Island, Florida 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located directly across from Tampa Bay, this gorgeous new custom luxury vacation rental looks out onto the beautiful bay waters from multiple large balconies. A rooftop deck provides outstanding 180 degree views of the turquoise waters, as well as the Anna Maria City Pier and the Sunshine Skyway...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful luxury beach front condominium for rent for the first time. There's only 2 condo's on the entire property. This condo is 3500 square feet including gourmet kitchen, dining room, living room with fireplace and built in flat screen TV. screened in lanai overlooking the Gulf of Mexico, den...
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    Anna Maria, Anna Maria Island 34210
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Sauna
    • Washer
    • DVD Player
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the crystal blue waters of the gulf. This is unquestionably one of Anna Maria's loveliest homes. This spectacular home...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    8 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The MI Happy Place  is excited to be under new ownership and management, with new amenities and improvements to make a beautiful, convenient, and relaxing location even better! When renting MI Happy Place Island Resort you will have eight bedrooms and four bathrooms sleeping twenty two making...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 8 Bedrooms, 4 Bathrooms, Sleeps 22
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    4 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Grill
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2016 New Custom 4 Bedrooms 4.5 Bathrooms resort size pool/spa Anna Maria Island home on a residential cul-de-sac and a boat dock in your back yard. This luxury home is quality built CBS and offers a chef's kitchen for all to enjoy. This Island retreat is located walking distance to the beach and...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Stunning 6 Bed 5.5 Bath Heated Pool Spa Water Slide FREE WiFi Gulf Views1 / 49
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
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    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2018
    Our family of 7 adults and 4 children thoroughly enjoyed our week long stay at The Big Kahuna. The house has a great holiday feel and is divided into two separate apartments...
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    About this property
    OCEAN VIEW is a brand new construction home that features 6 bedrooms and 5.5 bathrooms and a fantastic location-just a 1 minute stroll to the White sandy beaches at the 65th st access! This lovely property offers a private heated pool with a spa, water slide and grotto. The backyard is an oasis...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Hot Tub
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the crystal blue waters of the gulf. This is unquestionably one of Anna Maria's loveliest homes. This spectacular home...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Beachcomber, located at 3306 4th Avenue in Holmes Beach is the ideal, dream vacation home. This recently built gulf front home features a heated salt water pool and spa nestled in a tropical setting. It does not get any better than this! Luxurious furnishings, an elevator, a gourmet kitchen, a...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Save 20% Off Now through Oct. 31st! Located on the tranquil north end of Anna Maria island with a Gilligan's Island feel, this four bedroom mid century modern sprawling house has 120' of sandy beach overlooking the Sunshine Skyway Bridge and over 4,494 sq. ft. of living space, the property...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    8 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seagrass Flats Condo is a four unit complex located at 101 25th Street North in Bradenton Beach that features a large heated pool and bbq area. Immediately across from the beach, you can be on the sand in less than one minute. It’s a perfect vacation retreat for large family get- togethers and...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 8 Bedrooms, 8 Bathrooms, Sleeps 24
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    Mintfish, beautiful views across Bimini Bay! 4-Bed1 / 16
    (17)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
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    • Patio
    • Private Outdoor Pool (Heated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 April 2017
    Beautiful home relaxing away from it all. You can literally walk to all the wonderful places on the island or take the free trolly . This is my second time on the island and I...
    Reviewed 11 November 2016
    After a long time of research and a difficult choice between a lot of interesting opportunities at different locations along the Floridian Gulf Coast we settled for Anna Maria...
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    About this property
    Mintfish is a fantastic 4-bedroom waterfront rental home on Anna Maria Island from Pineapplefish Villas. Our latest and one of our most exclusive offerings: this home enjoys and incredible waterfront location with spectacular views across Bimini Bay. A single-storey, spacious rental, with open...
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    Location Information
    Anna Maria Island, Florida 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill for an evening of...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! Each unit features a large...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Hot Tub
    • Internet Access
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Beachcomber, located at 3306 4th Avenue in Holmes Beach is the ideal, dream vacation home. This recently built gulf front home features a heated salt water pool and spa nestled in a tropical setting. It does not get any better than this! Luxurious furnishings, an elevator, a gourmet kitchen, a...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 3 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 29 April 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 30 December 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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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
    • Housekeeping Included
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful vacation home in Bradenton Beach, has been fully renovated with brand new furnishings, and is actually two homes in one! You can enjoy a fantastic pool area for relaxing days in the sun or after a day at the beach. Right next to the heated pool, is a covered outdoor seating area...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
    • Patio
    • Air Conditioning
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Anna Cabana Resort, located at 3711 4th Avenue in Holmes Beach consists of four units, all located less than one block to the beach. All four units have been are decorated in a festive, tropical decor. There is also an onsite laundry room for provided for your use. A brand new heated pool has...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    8 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Seagrass Flats Condo is a four unit complex located at 101 25th Street North in Bradenton Beach that features a large heated pool and bbq area. Immediately across from the beach, you can be on the sand in less than one minute. It’s a perfect vacation retreat for large family get- togethers and...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 8 Bedrooms, 8 Bathrooms, Sleeps 24
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Ocean Views
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct Beach Front Home with 180 degree Gulf Views. Your backyard is a Private Beach and a beautiful view of Egmont Key & the Skyway Bridge. Walk to the Rod & Reel Pier where dolphins frolic every afternoon or walk to Pine Avenue for some local shopping. The living level has a full size kitchen,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Hooks Haven - 3bed beach front1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    • Terrace
    • Waterfront
    • Ocean Views
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2018
    We had a girls’ weekend and choose this location. Beach chairs, towels, washer-dryer, bikes.....perfect. Not a great view but only a few steps from the beach and central to...
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    About this property
    This 3 bedroom 2 bath home is on the north end of Anna Maria Island and can be combined with Pirate Cove (a separate building ) to make a 5 bedroom beach front vacation home. All bedrooms in Hooks Haven are Queen size. Two bedrooms are on the main floor and one is on the second floor. Spiral...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    $299 nightly till thanksgiving, Elevator, pool hot tub, outside t.v1 / 19
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Balcony
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2017
    We stayed at this home in 2016 and came back in 2017 and it has only gotten better. The location is get , close to the beach, trolley stops and shops. The backyard is private...
    Reviewed 15 August 2017
    This place was great it looked far from the beach on google maps but took us less then 5 minutes to walk there and with the beach cart and chairs provided it was a breeze.
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    About this property
    THE MAP OF THIS PROPERTY IS INCORRECT THE HOUSE IS LOCATE AT 4118 5TH AVE HOLMES BEACH. This ideally located 6 Bedroom 3.5 Bathroom is an amazing place to escape and unwind. Perfect place to get away with friends or family with it's large open spaces and outdoor sitting area. Angel Sea has every...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large 5 bedroom / 4.5 bath family home close to the best beach on AMI with a heated pool. The home is 130 steps to the beach, close to the stops for the free bus trolley which runs the island, close to the shops and restaurants of Pine Avenue. The home has a fully stocked kitchen, all the beach...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand new 6 bedroom 6.5 bathroom - SLEEPS 14 Comfortably. This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    Pet friendly
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    About this property
    Relax and unwind in this brand new custom built and professionally decorated 6 bedroom 4 bath home located just steps from both the Gulf of Mexico and the bay. This coastal style property boast luxury views from each room and features smart T.V.s in all the bedrooms as well as the living room and...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2311 Ave C is a combination of Addy's Inn and Island Retreat on beautiful Anna Maria Island is the home you will want to come back to time and time again. We are family oriented With 6 bedrooms and 4 bathrooms. The open setting has room for everyone. The living room is equipped with a 50' flat...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! Each unit features a large covered...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Patio
    • Balcony
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have some fun entertaining friends under the covered patio next to the refreshing pool. Brand new 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...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • DVD Player
    • Washer
    • Balcony
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Central Heating
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Anna Cabana Resort, located at 3711 4th Avenue in Holmes Beach consists of four units, all located less than one block to the beach. All four units have been are decorated in a festive, tropical decor. There is also an onsite laundry room for provided for your use. A brand new heated pool has...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    Honeyfish, stunning views across Bimimi Bay!1 / 15
    (32)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Patio
    • Internet Access
    • Waterfront
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    honeyfish lived up to everything written about it. location perfect. inside perfect.would return again and again if we had the time.and Zoe from pineapple fish was just...
    Reviewed 4 February 2016
    Anna Maria Island is a paradise away from the grind of everyday life. If you haven't been there, you must go to see and experience it for yourself! It was my family's first...
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    About this property
    Honeyfish is a fabulous, single storey vacation rental from Pineapplefish. Its location, on the edge of Bimini Bay, its nautically themed complete with boating artefacts, makes Honeyfish a water lover's dream luxury home on Anna Maria Island. Honeyfish is surrounded by the water and is perfect...
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    Location Information
    Anna Maria Island, Florida FL 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Cherryfish, a spectacular spacious 4-bed home!1 / 29
    (9)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    • Balcony
    • Porch
    • Cable/satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 2017
    Cherryfish is the ultimate vacation home. We have vacationed in Anna Maria numerous times and have stayed at Cherryfish twice it is our favorite home and we will stay there...
    Reviewed 4 July 2017
    We've just come back from an amazing holiday staying at Cherryfish. I couldn't recommend it enough for a large family or two sharing.Cherryfish is a beautifully maintained...
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    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. Distance to the Beach: 5 long blocks This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Gorgeous views,spectacular home!1 / 46
    (33)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Certificate of Excellence
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    • DVD Player
    • Washer
    • Grill
    • Cable/satellite TV
    • Balcony
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2018
    I can't believe I never wrote a review for our stay at this FABULOUS HOME! We booked it for our family for our wedding celebration and we love it from top to bottom! IT was...
    Reviewed 9 July 2018
    It pains me to give this beautiful home anything other than a stellar review. The owner, Chris, has been prompt and thorough with communication. The house itself is lovely and...
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    About this property
    WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A fantastic vacation rental for families or small groups that includes spacious patio area to enjoy your outdoor dining. Look forward to placing your your toes in the sand about one block away, or sailing on Sarasota Bay. Enjoy both units A & B when booking Beach Breeze Combo. Both units are easily...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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