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Anna Maria Luxury Holiday Homes

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    Travellers to Anna Maria are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    29 Matching Rentals in Anna MariaView all 198 rentals
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Pet friendly
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    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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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
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    Pet friendly
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    About this property
    VITAMIN SEA is a brand new construction home that features 5 bedrooms and 5 bathrooms and a fantastic location-just a 10 minute stroll to the White sandy beaches of BEAN POINT on the coveted north end of Anna Maria. This lovely property offers a private heated pool with a spa, The backyard is an...
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    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Housekeeping Included
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 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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    • Hot Tub
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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, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Waterfront
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A truly luxurious vacation experience is waiting for you at this canal-front Anna Maria vacation rental. This home is well-appointed with a private pool, dock access, five parking pots, and free trolley stops within walking distance. You'll have everything your family and friends need for an...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    • 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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    Jewel of the Bay1 / 24
    (6)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Grill
    • Internet Access
    • Patio
    • Air Conditioning
    • Washer
    • Waterfront
    • Cable/satellite TV
    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
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Anna Maria, Anna Maria Island 34217
    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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    • Waterfront
    • Patio
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    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With a stay at this Anna Maria Island vacation home, you’ll discover nearby beaches with flour-soft sand and gorgeous views of the bay right from the yard (in fact, a shady footpath leads right down to a private stretch of beach). It’s the perfect spot to get away from it all and enjoy a bit of Old...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wake to sun and waves at this casual beach house on Anna Maria Island, featuring ocean views from the balcony, a private heated pool, and dog-friendly accommodations to satisfy every member of your large group. Nestled just 250 yards from the powder sand at Magnolia Ave Public Beach on the north...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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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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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Private Outdoor Pool (Heated)
    • Grill
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    • Washer
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Following an extensive renovation in 2018, Dragonfly Harbour is now a handsome four-bedroom, five-bathroom private vacation home situated on a deep water canal in close proximity to Bimini Bay. This is a venue designed to allow our guests every opportunity to enjoy all facets of beautiful Anna...
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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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    • DVD Player
    • Patio
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    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Living The Dream' is a spacious 2,650 sq. ft. full-size private vacation rental home that has been recently remodeled with ALL NEW FURNISHINGS walk-in. (4) Bedroom, (3) Bath, accommodates (8) people: 2 Kings, 2 XL Twins, 2 Twins. NEW Stearns & Foster and new Sealy Posturpedic mattresses. The...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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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
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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Located on the tranquil north end of Anna Maria island with a Gilligan's Island feel, this luxury four bedroom mid century modern sprawling house has it's own private sandy beach overlooking the Sunshine Skyway Bridge...
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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, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Ocean Views
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    Pet friendly
    Kid friendly
    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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    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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    • Patio
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    About this property
    Welcome to Seagull Way!  This beautiful designer home is on Bimini Bay.  Seagull Way is a well appointed 4 bedroom/4 bath home that is comfortably furnished.  Sit back and relax in the high quality formal living room and dining room with luxurious furniture.  Enjoy a quiet night watching a movie in...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    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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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect spot for a large family getaway, this canalfront Anna Maria Island vacation rental home has room for everyone! Offering a dog-friendly atmosphere (dogs up to 50 lbs. are welcome with a small pet fee), parking for five vehicles, a private pool, and tons of space for the whole group, you...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 bedrooms and 2.5 baths directly on the beach in Anna Maria, Florida Enjoy spectacular views of the turquoise waters that are directly out the wall of glass and huge sliding doors. This high end Mediterranean style home has 3 bedrooms and 2.5 baths and best of all it is directly on the beach....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful Anna Maria Island duplex is the perfect destination for your next group Florida vacation. Comprising both Sugar Plum Hideaway West and Sugar Plum Hideaway East, this spacious rental offers room for up to 12 guests - and their dogs! Plus, you'll enjoy a big fenced backyard, a shared...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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