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Anna Maria Luxury Holiday Rentals

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    Travellers to Anna Maria are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    34 Matching Rentals in Anna MariaView all 229 rentals
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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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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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    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
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    Pet friendly
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    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
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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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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Housekeeping Included
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    • Central Heating
    • 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 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
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
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    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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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Central Heating
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    Pet friendly
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Ocean Views
    • Waterfront
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    Pet friendly
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    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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    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
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    Pet friendly
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    Reviewed 7 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
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    • DVD Player
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    • Balcony
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    • 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 October 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 3 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Gorgeous views,spectacular home!1 / 46
    (33)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. Distance to the Beach: 5 long blocks This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear,...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coconut Breeze is a custom home on the north end of Anna Maria in the quiet residential area in the sought after City Of Anna Maria. Offering 4 bedrooms / 4 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the luxurious heated pool,...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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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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    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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    • Waterfront
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    • DVD Player
    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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    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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    • Patio
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    • Balcony
    • 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    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 perfect rental for a family vacation or reunion...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill for an evening of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
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    Wave Crest: Stay ON The Beach! Gulf-Front Private Cottage With Breathtaking view1 / 25
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
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    Smoking allowed
    Reviewed 10 July 2017
    We stayed here at the end of June 2107. We have stayed in the same area on Anna Maria a few house to the north and love this area. It is quiet even when it's busy! Wave Crest...
    Reviewed 23 May 2016
    We were excited about renting Wave Crest due to the pictures and information we had previously received. However, nothing prepared us for this beautiful cottage with the...
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    About this property
    Take just four steps from Wave Crest's back door and sink your toes into the white sand beach of Anna Maria Island or enjoy views of the Gulf of Mexico from the deck, Florida room, or the four Adirondack chairs right on the sand. This gulf-front cottage is located directly on the beach and will...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Hot Tub
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Pier to Pier Paradise! This beautiful brand new luxury home is one of a kind!  Three stories high and ideally situated on Anna Maria's North end, the property is tucked into a quiet little neighborhood across the street from the beach and a short walk from the Rod and Reel pier, the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
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    • Balcony
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • Internet Access
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Grill
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    • Air Conditioning
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    • Parking
    • Waterfront
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
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    • Private Garden
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anna Maria Canal Home with 36 ft Private Pool and Spa. Newly remodeled home just 2 short blocks to the beach and located on a quiet canal street. You will love the stylish decor at this 2 bedroom, 2 bath ground floor home. Enjoy 1300 squ ft of living area with tile floors, granite counters, brand...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Patio
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    • Grill
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!1 / 23
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 May 2018
    My family and I had a wonderful stay at Beach Nest. Liza was more than accommodating. We had to cancel due to unforeseen reasons and she allowed us to pick from a number of...
    Reviewed 24 February 2017
    Beach Nest is wonderful. Decorated with flair and beachy elegance, it feels like a home, not a rental. There is everything you need and more. You can walk to the beach with your...
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    About this property
    Water lovers too! Ahhhh-Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! Vacationers, dreamers, honeymooners, would-be family-reunion...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Terrace
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Brand New Rental!   Sea Haze is a mere 212 steps to the beach and the crystalline gulf! As you take your short walk to the gulf beaches, you will take in the sights of the dense banyans, spectacular homes of Park Avenue and the tropical sea grapes. Sea Haze is perfectly located - west of Gulf...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and soak in the unbelievable views of the Gulf of...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
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    • Internet Access
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    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, 3 Bathrooms, Sleeps 8
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    Bradley's Beach House: Private Pool Home on Pine Avenue Just Steps from Beach!1 / 22
    (13)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 February 2018
    We rented Bradley Beach House for Super Bowl week and couldn’t ask for a better place to stay with friends and family for the week! Clean, well kept property close to everything...
    Reviewed 30 June 2017
    Great location! Steps to the beach and walking distance to nice shop and restaurants. But wish we would have known construction was going on at two different properties right...
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    About this property
    Steps from the white sand beaches of Anna Maria, this four-bedroom, three bath, elevated house is just the place to build sand castles and memories! Located on Pine Avenue in Anna Maria, this charming beach vacation rental with a newer backyard pool is beckoning you to start your vacation now. A...
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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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