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Anna Maria Island Luxury Vacation Rentals

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    Travellers to Anna Maria Island are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    154 Matching Rentals in Anna Maria IslandView all 1,026 rentals
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    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    About this property
    Treat yourself to the experience of a lifetime with this luxury Anna Maria Island home with a private heated pool, balcony with gorgeous views, and an unbeatable location right on the beach. Situated directly on the pristine white sands and warm waters of the Gulf of Mexico, this extravagant home...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Ocean Views
    • Hot Tub
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this brand new 5 bedroom, 4 bathroom beach home just a one minute walk to the famous Anna Maria Island beach. The beach stretches for miles in each directions. Feel the powdery sand between your toes and enjoy the warm Gulf waters. This home has all the style and deluxe amenities you...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 22, 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 May 1, 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
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    • 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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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the elegance of this three-bedroom Holmes Beach penthouse, a beachfront retreat with direct access to the sand, a wrap-around balcony with stunning Gulf views, and shared amenities that include a heated swimming pool, a patio, and a grilling area. Stunningly situated on the west coast of...
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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: 4BR INCREDIBLE Waterfront Home1 / 24
    (5)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 May 20, 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 June 5, 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 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 amazing...
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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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    • DVD Player
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 27, 2015
    We stayed at Casa Playa for the week after Christmas over New Years! The location is amazing...close to everything you need except a grocery store. The weather was perfect, the...
    Reviewed April 9, 2014
    We stayed here for the full month of March and very much really liked this unit. The owners ( Scott Deb ) were very nice, as they were wanting to make sure we had everything we...
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    About this property
    This Bradenton Beach vacation home is actually two rentals in one, in the middle of all the fun and beaches that Bradenton Beach can offer. The rental package sleeps up to 20, and everyone can enjoy the 2 private swimming pools. This is a fully equipped rental home on Anna Maria Island, with...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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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
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 10, 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 November 8, 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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    Location Information
    Anna Maria Island, Florida 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    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 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    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, 5 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Housekeeping Included
    • Patio
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    • Central Heating
    • Waterfront
    Suitability
    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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    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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    • Internet Access
    • Cable/satellite TV
    • Washer
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    • Balcony
    • Patio
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special May Pricing - The Best Time To Be On AMI! Welcome to Yellowbird; your home away from home at the north end of beautiful Anna Maria Island. Here you will enjoy unforgettable views and sunsets over the white sands of the Gulf from the home's multiple decks. This 4 bedroom custom home is the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand new Stunning 3 bedroom 3.5 bathroom + den with bunk beds. 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 heated pool in your own backyard oasis. This house has every luxury you could want,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At 5 bedrooms and 3 full bathrooms, this is a tropical oasis waiting for you on Anna Maria Island. HEATED POOL AND SPA 2 MINUTE WALK TO THE BEACH Straight down the road to the beach, and around the corner to restaurants, pubs & stores. Featuring a huge heated pool to relax in after your busy day,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 4, 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, 4 Bathrooms, Sleeps 16 Quick View
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    • Grill
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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, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    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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    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
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 26, 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 November 10, 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
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    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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    510 Bayview1 / 20
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Balcony
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    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 29, 2016
    Had a fantastic week here nine adults and we did not bump into one another once 4double rooms and 1 twin all with their own bathrooms pool area great pity that the water...
    Reviewed December 29, 2015
    I recently stayed at this beautiful house and it was the best decision I made for the holiday. First, the rental company was so easy to work with. There was no stress at all...
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    About this property
    510 Bayview - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Island Elegance for the whole family!~ Distance to the Beach: 2 blocks Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and...
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    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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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Ocean Views
    • Waterfront
    • Central Heating
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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
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    • Ocean Views
    • Balcony
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 7, 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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    $399 NIGHTLY UNTIL THANKSGIVING 2019,  POOL, HOT TUB, ELEVATOR, BLOCK FROM BEACH1 / 19
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Balcony
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 13, 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 August 14, 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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    Beautiful home, minutes from beach, bikes, beach gear, free heated pool/ spa1 / 50
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 20, 2017
    This house has it all. Beach chairs, beach towels, boogie boards, bikes, and so much more. Thr pool and hot tube are very large and heated. The house is very well kept. The...
    Reviewed August 9, 2016
    We thoroughly enjoyed our stay at this home. It was just as pictured. We especially enjoyed the beach bikes that were provided.
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    About this property
    HEAT POOL, SPA, BIKES AND BEACH GEAR FOR YOUR USE This stunning brand 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 salt water heated pool in your own backyard oasis. This house has...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
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    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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    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
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    • Private Outdoor Pool (Heated)
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful gem of a home is located in the much coveted north end of Anna Maria Island in the City of Anna Maria. It is a single family home located on a quite street. Just a 2 minute walk to the gorgeous white sand beaches on the bay side of the island and about a 10 minute walk to the sugary...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    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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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 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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    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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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    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 34218
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for luxury, then this Anna Maria Island vacation rental home is the perfect getaway! With a private pool, ocean views, and even roof top deck, you'll have everything you need for a memorable stay. Located on the coveted west of Gulf Drive strip, you'll be just steps from the...
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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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    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
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    • Waterfront
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 2, 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 February 3, 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)
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    • Balcony
    • Porch
    • Cable/satellite TV
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 31, 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 July 3, 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
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. Distance to the Beach: 5 long blocks This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This five bedroom, three bath property is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
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    Pet friendly
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    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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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Gorgeous views,spectacular home!1 / 46
    (32)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    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...
    Reviewed June 4, 2018
    unfortunately for our 2 weeks on AMI we had lousy weather..... which meant we spent more time in the house than we had originally planned. The rooms are spacious and nicely...
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Terrace
    • DVD Player
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    • Ocean Views
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand new home is on Anna Maria Island and located across the street from beatiful white sand beach access. The house is huge and is professionally decorated. It has a very cool game room on the first floor with full sized Classic Arcade Games, Elecronic Dart Board, Foos Ball Table, Ping...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Luxury awaits with this brand-new gulf-front Anna Maria Island rental! Leave behind your worries and enjoy upscale amenities, along with a prime oceanfront location and quick access to the beach! Warm gulf waves and soft sands are just across the street, so don't hesitate to start your day with a...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Waterfront
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    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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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Your family will always remember the time you spend at this four-bedroom Holmes Beach retreat, a luxurious Anna Maria Island home with a private heated pool, a roof deck with breathtaking views of the Gulf of Mexico, and an enviable location mere steps from the beach! This newly built home sits on...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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 cottages known as...
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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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located at the prestigious north end of Anna Maria, Blue Waters is a beautiful resort-style villa, just minutes walk from the gorgeous white sand beaches of Anna Maria Island and a few blocks away from the individual shops and restaurants of Pine Avenue. Situated on a peaceful residential street,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    A special time awaits you at this updated beach house on Anna Maria Island. Featuring a dog-friendly attitude, a private lagoon pool, and easy access to Bean Point Beach, this house will leave you dreaming about the tropics for weeks after your trip. Located at the tip of Anna Maria Island, a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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