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Villas in Anna Maria Island, FL

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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 4
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 9
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The right company can be a retreat all in themselves. So when you’re looking for an escape in Anna Maria Island with someone special, consider a week spent... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 10
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Enjoy quiet seclusion of this bayside location. This 3BR/2BA spacious canal front home is located on a cul-de-sac street. The home has a fully equipped kitchen, screened lanai, boat dock, washer/dryer, dishwasher and garage. There is one King size bed and two queen size beds. Comfortably furnished.... View all property information
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    Anna Maria, Anna Maria Island
    1 / 28
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Runaway Bay 230 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. Runaway Bay ----Large complex ---right across the street from the beach. Easy beach access. Largest heated community pool on the Island, tennis, fishing dock, shuffle board and clubhouse. Upstairs unit with views of... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 24
    Bradenton Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 3 Bedroom, 2.5 Bath (Sleeps 6) – “South Beach Village” – 111 10th Street in Bradenton Beach When you arrive to “111 South Beach Village”, located at 10th... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 28
    Holmes Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Visit this marvelous private custom-built vacation rental home just a few steps from the white sandy beaches of Anna Maria Island and the Gulf of Mexico. 6... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 6
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Gulf Watch 210 - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people. Don't Forget Your Fishing Pole!~ Gulf Watch Condo---2 bedroom, 2 bath condo in 32 unit complex with heated pool. Gulf to Bay setting. washer/dryer in unit. About 1200 square ft. Convenient walk to... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 23
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Accommodating up to six guests for a fun laid back beach vacation, Casa Sierra 205 B offers the perfect two bedroom, two bathroom getaway for you and your... View all property information
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    Holmes Beach, Anna Maria Island
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    1 / 18
    Anna Maria
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 2 Bedroom, 1 Bath (sleeps 4) - 21 Palms A - Anna Maria This newly remodeled and updated island vacation rental duplex is just a stroll to the Gulf of... View all property information
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    Anna Maria, Anna Maria Island
    1 / 24
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Located in beautiful Bradenton Beach, “Sunset Terrace” is the perfect Anna Maria Island vacation rental for 4 guests right on the Gulf of Mexico! This 2nd... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 16
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; You’ll be in vacation mode from the second you drive up and see sunshine glinting off the rich, bronze walls and eye popping turquoise details of Bradenton... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 13
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Key Lime Cottage East, 3 bedroom 2 bath new duplex with private heated pool.  Sleeps up to 6. Key Lime Cottage East welcomes you to this recently re-done... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 2 Bedroom, 2 Bath (sleeps 6) - 'Anna Maria Island Club' - 2600 Gulf Drive N. Unit #18, Bradenton Beach Welcome to Anna Maria Island Club! This complex... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 24
    Holmes Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;  It’ll be hard to miss the style, taste, and indulgence waiting for you at this three story, Holmes Beach vacation home. From the moment you pull into the... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 30
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Runaway Bay 257 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 5 people. Runaway Bay ----Large complex ---right across the street from the beach. Easy beach access. Come and relax on Anna Maria Island, the best kept secret in Florida! We are located in beautiful Runaway Bay , Bradenton... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 12
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 2 Bedroom, 2 Bath (sleeps 4) - 'Katie's Beach Bungalow' - 108 8th Street So., Bradenton Beach This elevated, rental beach house is constructed in the... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 24
    Holmes Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Spend your Anna Maria Island vacation in five star luxury when you visit “Fernweh”. This new Holmes Beach vacation rental offers both a stylish and relaxing... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 30
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   Enjoy a magical sunset in this well maintained Gulf of Mexico direct beachfront Condo... Perfect get away condo. The large heated pool and nestled right... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
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    1 / 26
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; This newly remodeled and updated island vacation rental duplex is just a stroll to the Gulf of Mexico and our beautiful sunsets. (3) Bedroom, (2) Bath,... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 6
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    About this property
    Mermaid Manor is a beautifully updated cottage. Perfect for couples and small families, it sleeps four. Beachy chic décor. Enjoy a shaded sitting area with access to a gas grill. It is located on the gulf coast of Florida in a quiet location known as Anna Maria Island, just steps from the white... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 24
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Bedroom, 1.5 Bath (sleeps 5) - 'Sandy Pants' - 133 White Avenue, Anna Maria Remodel January 2015! Be the first to see all the new decor, appliances,... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 11
    Anna Maria
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Chic and cozy vacation rental nestled right between the Tampa Bay and the Gulf of Mexico.   (2) Bedroom, (1) Bath, accommodates up to (6) people: 1 Queen, 2... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 23
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Relax and unwind in the casually luxurious Anna Maria Island vacation rental home “Sapphire Beach House”. This four star rental has everything experienced... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 23
    Anna Maria
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The perfect spot for a large family getaway, Waterfront Retreat is a stunning six bedroom, 3 full bath/2 half bathroom, canal front Anna Maria Island... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 24
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Just a short stroll from Gulf of Mexico beaches, Anna Maria vacation rental “Beach Pearl” offers a luxurious getaway experience. All the amenities you would... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 23
    Anna Maria
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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    About this property
    'South Cay' is an absolutely beautiful house on Anna Maria Island, located in Anna Maria (not in Holmes Beach). There are only 11 houses between South Cay and the Gulf of Mexico beach, so this property is very close to the beach. Walk out the house, look to your right, and you see the beach access... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 24
    Anna Maria
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Jan 31 : Saturday check-in required, Saturday check-out required.; A unique and truly luxurious vacation experience is waiting for you at Anna Maria vacation rental “Cayman Bay” located on the coveted north end of Anna Maria... View all property information
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    Anna Maria, Anna Maria Island
    1 / 19
    Anna Maria
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Bayou 5B - Condo ground floor 2 Bedroom / 1 Bath, maximum occupancy of 4 people. Located on historic Pine Ave., Bayou 5B has great water views and a private dock. You can walk across the street to the Anna Maria City Pier and to shops and restaurants. This comfortable unit is very well maintained.... View all property information
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    Anna Maria, Anna Maria Island
    1 / 18
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Elegant and tropical poolside paradise holiday rental. (4) Bedroom, (3.5) Bath, accommodates to (12) people: (2) Kings, (1) Queen, (4) Twin Bunks, (1) Queen... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 23
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
    About this property
    LUXURY RENOVATED 2 BR/2 BA ISLAND CONDO - DIRECTLY ON GULF OF MEXICO Private, Peaceful, Comfortable * Relax, Rejuvenate * Screened-in Dining Balcony/w Hi-Back Swivel Rockers, Overlooking Heated Pool, Beach and Gulf of Mexico * Spectacular Water Views, Nightly Show at Sunset, Ocean Breezes, and... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 25
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The casual and spacious Anna Maria Island vacation rental “North Beach Village 67” is a fabulous way to make your vacation amazing! Just two blocks from the... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 33
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    • x
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    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Spectacular, direct gulf front condo with an enviable Gulf front location, on the beach with gorgeous views and breath-taking sunsets! (2) Bedroom, (2) Bath,... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 13
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Welcome to Palm Tree House, a luxurious and spacious end-unit condo located directly on Holmes Beach in the heart of Anna Maria Island. Your home away from home is just steps from the beautiful powder white sand and soft waves of the Gulf of Mexico. This island oasis is completely updated and... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    Anna Maria
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 4 Bedroom, 2 Bath (sleeps 8) - 'Blue Heron Beach House' - 117 Peppertree Lane in Anna Maria.  Welcome to “Blue Heron Beach House”! This adorable Anna Maria... View all property information
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    Anna Maria, Anna Maria Island
    1 / 26
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Paradise Pointe, located in the quiet north end of beautiful Anna Maria awaits the vacationer in you. This picture perfect ground level three bedroom two... View all property information
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    Anna Maria, Anna Maria Island
    1 / 28
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beach Baby is situated on the north end of Anna Maria and is only 4 houses to the gorgeous Gulf waters that the Island is famous for. This great two story house offers a private Heated Pool with Hot Tub and two hammocks on which you can take in the island sun. The main living level contains the... View all property information
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    Anna Maria, Anna Maria Island
    1 / 30
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   Harmony House is such a special place! Remember days gone by in this Key West style holiday rental with a c'ocktail-style' sparkling pool in a tropical... View all property information
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    Anna Maria, Anna Maria Island
    1 / 24
    Anna Maria
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 4 Bedroom, 2.5 Bath (Sleeps 8) - “ 3 Mermaids” - 120 Oak Avenue in Anna Maria. A fun and relaxing way to spend your vacation on Anna Maria Island, “3... View all property information
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    Anna Maria, Anna Maria Island
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    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; (3) Bedroom, (2) Bath (Sleeps 6) – “Sugar Plum Hideaway East”- 114 Mangrove East in Anna Maria You’ll be pleased when you reserve Anna Maria Island... View all property information
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    Anna Maria, Anna Maria Island
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    5 of 5 stars (2) Excellent
    Anna Maria
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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... View all property information
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    Anna Maria, Anna Maria Island
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    ** Call +1 908 236 2966 to inquire about this property Island Paradise is just that - the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any better than... View all property information
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    Holmes Beach, Anna Maria Island
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Recently renovated, 2 bed 2 bath Villa perfect for families, couples or a small group of friends. Located in a quiet neighborhood with an easy 3-minute walk to the gorgeous white sand beaches of the Gulf of Mexico. You are less than a mile from historic Pine Avenue shops, restaurants, and the Anna... View all property information
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    Holmes Beach, Anna Maria Island
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    Anna Maria
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Get ready to fall in love with the vacation rental of your dreams when you visit “Sea Song”! This stunning direct gulf front Anna Maria vacation rental has... View all property information
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    Anna Maria, Anna Maria Island
    1 / 10
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The various shades of blue throughout Sea's the Day make this a  water lover's dream vacation cottage. Sitting about 200 steps to the beach access, it's like... View all property information
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    Anna Maria, Anna Maria Island
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    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • x
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 4 Bedroom, 3.5 Bath (Sleeps 12) - “Mango Tango” - 145 50th Street in Holmes Beach. Experience a tropical memory maker vacation of a lifetime when you... View all property information
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    Holmes Beach, Anna Maria Island
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    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   Southern Comfort is a luxury three bedroom vacation home less than two blocks from the beach. (3) Bedroom, (2.5) Bathroom, accomodates up to (8) people: 1... View all property information
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    Holmes Beach, Anna Maria Island
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    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • Smoking allowed
    • x
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Find everything that makes a fun beach getaway on Anna Maria Island memorable when you stay at Holmes Beach vacation rental home 6313 North Beach Village.... View all property information
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    Holmes Beach, Anna Maria Island
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    Holmes Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Seabreeze Villa is a fabulous home for your vacation on Anna Maria Island. This beautiful Mediterranean designed home is located in central Holmes Beach, and is within walking distance of shopping, restaurants, and the white sand beach! This spacious home is equipped with a fantastic kitchen,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island