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Holiday Rentals 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 / 25
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 18
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 13
    3 of 5 stars (1) Average
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 10
    Bradenton Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2307 AVENUE C - Duplex 3 Bedroom / 2 Bath with pool, maximum occupancy of 6 people. Come and swim with the turtles!~ Adorable and totally renovated 3 bedroom and 2 bath duplex on the second floor, one street back from Gulf Drive on the beach. The first floor is storage for pool toys, pool and... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 34
    4.5 of 5 stars (2) Very good
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    There's no better way to enjoy Anna Maria Island than Sand Dollar! Centrally located in a mellow, residential neighborhood, Sand Dollar is a half block to the free Island trolley and a quick 6 minute walk to the beach 3 blocks away. Also in close proximity are many of the Island's best eateries.... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 22
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    The best of both worlds on the Island is where the Gulf meets the Bay at the "Tip" of Island in Anna Maria. Beautiful Sunsets, Fishing Piers, a Park and Bird Watching can be found at the Northern tip of the Island. This 2BR/2BA plus a Loft is located one property from the beach access at Bean... View all property information
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    Anna Maria, Anna Maria Island
    1 / 11
    4.5 of 5 stars (4) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    LaPlayita 5 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 6 people. Unforgetable Vacations Created Here!~ Vaulted Ceiling in Living Room. Upper Level Master Bedroom/Bath. Lower Level Bedroom/Bath. Telephone, Cable TV, wi-fi internet service available. Fully Furnished.Covered Parking.... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 14
    4.5 of 5 stars (2) Very good
    Holmes Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    3011 Ave E-1 - Triplex Condo 4 Bedroom/ 2 Bath , maximum occupancy of 8 people. Wouldn't you rather be at the Beach?~ Nestled in a quiet residential area just one half block from the beach, is a tri-plex offering a pleasant environment for individual guests or the family clan. Rent all units,... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 30
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Completely Remodeled 3 bedroom/2 bath home with private Heated pool. Beautiful new tile, Granite countertops, all new appliances, and living room overlooking the heated pool. Bright, open kitchen, dining and living area! Sleeps up to 8. 1500 Sq. ft. 204 Archer Way, Anna Maria 3 Bedroom/2Bath... View all property information
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    Anna Maria, Anna Maria Island
    1 / 15
    Bradenton Beach
    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.; Includes swimming pool and partial views of the gulf, and only 1/2 block from the incredible beaches of Anna Maria Island, this adorable vacation rental in... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
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    1 / 23
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Porch
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    About this property
    Beach-style living at its best will be evident when you arrive at Breeze On In. Located just three blocks from the beautiful white sand beaches of Anna Maria Island in Holmes Beach, this lovely home will keep you coming back year after year. This beautiful vacation rental boasts a newly remodeled... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 16
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Private Garden
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    About this property
    This is the Florida view you have been dreaming of... Single family home situated at the end of a natural canal with a view over the water. Sit outside, fish off our dock, take out the kayaks, or just walk steps across the street to the beach! This is not your typical beach rental. It is our... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 22
    5 of 5 stars (29) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
    Location Information
    Anna Maria Island, Florida
    1 / 23
    4.5 of 5 stars (4) Very good
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Terrace
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    Pelican Cove 6 - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 6 people. Florida's Finest Beach to Bay Resort with a Community poo! The Crystal Blue Waters and Golden Sunsets are Unforgetable!~ Located near the shops and restaurants on Bridge Street, Pelican Cove lures those who... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 24
    5 of 5 stars (8) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This vacation rental has been completely refurbished, with tile floors and ceiling fans throughout and a beautiful heated pool. Centrally located on Anna Maria Island, Twin Villa is a short two block walk to the beach. The well-appointed kitchen is equipped with a vegetable sink, stainless... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 34
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Watch the Dolphin's play from your deck, covered patio or right on your beach! You will enjoy this direct Bay Front home that has direct Bay Views from almost every room and the outside deck. The owners have done a wonderful job decorating this charming 2BR/2BA home in the true Island spirit! This... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 39
    5 of 5 stars (2) Excellent
    Anna Maria
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Waterfront
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    • x
    About this property
    Newly Remodeled 1 Bedroom/1 Bath Cottage in a serene north end location. The allure of the Gulf of Mexico Beach just 250 steps away. A back yard dock on Lake LaVista Bayou with a patio table, umbrella, and sling back chairs. Launch the provided kayaks right from the dock or choose to bring your own... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 17
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This elevated 2BR/2BA home is located directly across from the beach at the quiet North end of the Island. Enjoy the gulf breezes from the large screened lanai. Fully equipped kitchen including a dishwasher. Laundry room with Washer/Dryer. Bed sizes are a Queen bed, two twin beds and a sleeper... View all property information
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    Anna Maria, Anna Maria Island
    1 / 24
    Holmes Beach
    3 Bedrooms, 3 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.; Updated Holmes Beach Island home just steps to the Gulf of Mexico beaches. Enjoy this vacation rental with a caged heated pool and a brand new paver area... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 24
    4.5 of 5 stars (4) Very good
    Anna Maria
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • x
    About this property
    With its luscious landscaping, eclectic look and colorful Key-West style, Simpatico could be right out of <em>Coastal Living Magazine</em>. This vacation rental bungalow is perfect for the ideal secluded island vacation! Located on the north end of Anna Maria Island, this canal home, with a boat... View all property information
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    Anna Maria, Anna Maria Island
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    1 / 24
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    109 Willow Casa Nana - Cottage 2 Bedroom / 2 Bath , maximum occupancy of 6 people. Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building happy summer memories right in this spot, and they... View all property information
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    Anna Maria, Anna Maria Island
    1 / 3
    4 of 5 stars (1) Very good
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Ocean Views
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    • x
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    Beautiful studio condo on Bradenton Beach with the BEST sand and beaches~just voted in 2015!<BR>KITCHEN, MURPHY BED, QUEEN SLEEPER SOFA, WASHER/DRYER, WIFI, CABLE.<BR>Slight view of the gulf from the balcony which overlooks the heated pool.<BR>Beach side so there is NO crossing the street. Quiet... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 28
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    Pelican Cove 4 - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 5 people. Florida's Finest Beach to Bay Resort with a Community poo! Stay, Play and enjoy Beautiful Gulf Views!~ Located near the shops and restaurants on Bridge Street, Pelican Cove lures those who appreciate a lively... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 24
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
    About this property
    Kick off your shoes and get your relaxation on at LimeMariaVille! Located on Anna Maria Island in Holmes Beach, this is the perfect vacation rental for you, your family and friends. This beautiful three bedroom, 2.5 bath home has all the amenities and more for a fun time! A fully-equipped kitchen... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 38
    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) - 'Heron-Dolphin' -706 Rose Street in Anna Maria. Anna Maria Island vacation rental home “Heron-Dolphin” is a fabulous... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 22
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Palm Court Villas are located in the heart of Anna Maria Village with a short stroll to great local restaurants, shops and the Community Center. Beautiful white sand beaches are just one short block away. You have direct beach access to one of the best beaches on the Island. This section of beach... View all property information
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    Anna Maria, Anna Maria Island
    1 / 22
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Palm Court Villas are located in the heart of Anna Maria Village with a short stroll to great local restaurants, shops and the Community Center. Beautiful white sand beaches are just one short block away. You have direct beach access to one of the best beaches on the Island. This section of beach... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 36
    5 of 5 stars (27) Excellent
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    About this property
    TripAdvisor EXCELLENCE AWARD | Exquisite direct beachfront condo with 2 ensuite bedrooms, den, and 2 baths | Stunning views | Sleeps 4 | Open kitchen | Granite counter tops | Large storeroom at beach level with beach furniture | Beach side screened lanai with stairway direct to beach | Ceiling fans... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 20
    Bradenton Beach
    1 Bedroom, 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.; Located in the heart of Anna Maria Island’s Bradenton Beach, the Bay View Inn 101 is a quaint one bedroom one bathroom condominium accommodating up to 4... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 24
    4 of 5 stars (5) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Part of the Spinnakers Vacation Cottages Cabin 2 is a one bedroom, one bath cottage nestled in a lush tropical landscape. Surrounded by palms, plumeria, jasmine and more palms you will find our little paradise the perfect spot for a getaway! Cabin 2 offers a comfortable queen size bed as well as a... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 35
    5 of 5 stars (1) Excellent
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Looking for that place to kick back and relax your cares away? Check out ‘Triple Play Guest House.' There's a triple chance to play: (1) walk to the beach, (2) lounge in the pool or spa or patio or (3) launch a kayak, fish or just relax on one of our two docks on the canal. Nothing quite compares... View all property information
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    Anna Maria, Anna Maria Island
    1 / 18
    3 of 5 stars (1) Average
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Sandy Point 106 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 5 people. This comfortable 2 bedroom, 2 bath condo is in a great location; a quiet residential area yet within easy walking distance to the beach grocery, pharmacy and restaurants. In addition, there is a trolley stop directly in... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 21
    5 of 5 stars (23) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    700 ft. of pristine beach frontage, only 16 Units! This beachfront condo is located right on Holmes Beach. Two bedroom, 2 bath. One of the largest pool on the Island. Beach sand ranks in the top 5 worldwide. New elevator and all granite kitchen. Anna Maria has been voted the worlds "best kept... View all property information
    Location Information
    Anna Maria Island, Florida
    1 / 15
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Bradenton Beach Club 247 - Condo 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Bradenton Beach Club 247 let's you enjoy the best of the bayside and the beachside of Anna Maria! This 3 bedroom, 2.5 bathroom townhouse with a private elevator* is just steps away to the beautiful beach of the... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 20
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This condo has just been totally renovated and redecorated in a contemporary yet comfortable style. The apartment is a ground floor unit with easy access to the pool, Gulf of Mexico and Bay of Sarasota. Runaway Bay resort features 13 acres of lush landscaping and is full of amenities including the... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 10
    Holmes Beach
    2 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.; When a starfish needs to get away, it is more than prepared to detach an arm in order to do that. Don’t let yourself get that stressed! Stay for a week in... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 21
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    Anna Maria Island Club 45, Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 4 people. Community pool. 'Are you ready for this?' Anna Maria Island Club--- Stunning Panoramic Views of Gulf of Mexico. Come experience the ultimate in Island luxury on Anna Maria Island with this... View all property information
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    Bradenton Beach, Anna Maria Island
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    About this property
    20771st Beach Villa -Duplex 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. The perfect spot for the budget-conscious, beach-loving vacationer! This comfortable and clean 2 bedroom/2 bath elevated duplex is only 200 yards from the fabulous white sand beach and crystal-clear waters of the Gulf... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 27
    Bradenton Beach
    4 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.; This home provides you with your own private pool. It has virtually everything you need for a perfect Island vacation. This home has a private pool and is... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 17
    4.5 of 5 stars (5) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This charming 2 Bedroom 2 Bath is the fourth house from the gorgeous white sand beach on the Gulf of Mexico. Remodeled and updated, this fully furnished home features 1450 sq ft, plus garage and patio. Amenities include living room plus family room with TVs in both, fully equipped kitchen, laundry... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 40
    Holmes Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Beautiful, brand new, 5 bedroom/3.5 bath home with large privacy fenced lushly tropical landscaped yard, heated pool, hot tub, elevator, and ping pong table! There is large covered patio by the pool area with outside dining options and plenty of seating in the large great room area. The kitchen... View all property information
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    Holmes Beach, Anna Maria Island
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    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.; 3 Bedroom, 2.5 Bath (sleeps 6) - “North Beach Village” - 6250 unit 68 Holmes Boulevard in Holmes Beach. For a relaxing and casual Anna Maria Island... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    4 of 5 stars (6) Very good
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    The adorable Coastal Cottage, located in the laid-back city of Anna Maria, is the perfect place to take a totally carefree vacation. The white sand beach of Anna Maria Island and the azure blue waters of the Gulf of Mexico are only a short stroll from this delightful three-bedroom, two-bath... View all property information
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    Anna Maria, Anna Maria Island
    1 / 24
    5 of 5 stars (4) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    You will definitely be dreaming about the beach when you walk into this open and well-appointed two-bedroom elderly- and family-friendly Holmes Beach condo. Whether you are relaxing watching dolphins and sunsets from your private balcony overlooking the Gulf of Mexico or taking a dip in the large... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 19
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    • x
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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.;  Elegant and tropical poolside paradise holiday rental. (4) Bedroom, (3.5) Bath, accommodates to (11) people: (1) King, (2) Queens, (1) Twin, (1) Double, (1)... View all property information
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    Holmes Beach, Anna Maria Island
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    Holmes Beach
    4 Bedrooms, 4 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.;   Welcome to Sea Shell and Sunsets! Brand New Custom-built Island Home located at 105 78th Street, Holmes Beach, Anna Maria Island, FL -- (4) Bed: (4.5)... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 22
    5 of 5 stars (3) Excellent
    Anna Maria
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Grill
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    • Private Outdoor...
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just around the corner from the Rod & Reel Pier, Bayfront Park, and just a couple of blocks to Fabulous Bean Point Beaches and Sunsets. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor lounging... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 20
    4 of 5 stars (1) Very good
    Anna Maria
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • ?
    About this property
    Located in the heart of Anna Maria Village this recently updated one bedroom apartment is located just a few houses from the beautiful Gulf Beaches. Direct beach access with no streets to cross! 146 steps to the beach and less than a 2 minute walk. Bring your boats and wave runners as there is... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 19
    Anna Maria
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    This vintage Island beachfront home has 4 sleeping rooms and 2 bathrooms. Enjoy the charm of yesterday in this great family beach house located between Palm and Magnolia Avenues. Excellent Gulf views, steps to beautiful, white sandy beaches. This home includes a washer/dryer, dishwasher, several... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 16
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
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    • DVD Player
    • Sauna
    • Washer
    • Patio
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    • Satellite TV
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Gorgeous, fully furnished, 2BD/2BA ground floor condo, directly on the Bay! Wake up each morning with gorgeous sunrises from the master bedroom or living room. You can sit at your dining table, or lanai table, and watch the boats, dolphins, birds on the water. The view is absolutely amazing!!... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island