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Villas in Anna Maria Island, FL

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    Travellers to Anna Maria Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 24
    4 of 5 bubbles (1) Very good
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    1 / 24
    4 of 5 bubbles (6) Very good
    Anna Maria
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    5 of 5 bubbles (4) Excellent
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 28
    5 of 5 bubbles (38) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    From the same owners of A Lime Cottage (p277325), who've been recognized as TripAdvisor "rated excellent" vacation rental, Flipkey 2012 and 2013 Top Vacation Rental, 2012 Top Rental Manager", we're delighted to now have Lemon Cottage. <BR><BR>Nestled in a quiet residential boating community across... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 8
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    Location Information
    Anna Maria Island, Florida 34217
    1 / 24
    4.5 of 5 bubbles (10) Very good
    Anna Maria
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    BON AMI will be your "good friend" after a vacation stay. Located on the north end of Anna Maria Island and a short distance to Bean Point and its beautiful beaches, this elevated pool home will beckon you back year after year! Beautifully decorated, this three-bedroom, two-bath vacation rental is... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 12
    4.5 of 5 bubbles (14) Very good
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Apartment 1 is located on the lower level, with a private patio in the back, and the ability to walk straight out to the heated swimming pool. It has one bedroom with a queen size bed and there is a pull-out sofa in the living room. If you are looking for a great, affordable place to stay on Anna... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 27
    5 of 5 bubbles (3) Excellent
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Adorable and Updated 2 BR/2BA villa with a private heated pool. This villa is located on a quiet residential street, just a short walk to the beautiful beach, with no busy streets to cross to get there, and easily walkable to the 'downtown' Holmes Beach area for shopping and restaurants and more!... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 17
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Please note these Check-in Day Requirements for this property: Feb 18 - Apr 21 : Saturday check-in required, Saturday check-out required. Apr 29 - Apr 19 : Saturday check-in required, Saturday check-out required. Palm Cottage is a beautiful newly remodeled vacation rental located in Bradenton... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    1 / 36
    4.5 of 5 bubbles (2) Very good
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    COMPLETELY REMODELED 2 bedroom/ 2 bath duplex unit. Tastefully furnished and decorated, you will feel right at home. A plush King bed in one bedroom and queen bed in the other. It's just over a block to the beach, and a block to the free Island trolley! Elevated, with one car garage underneath... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
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    1 / 23
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Let the "Good Times" roll at this original and fun Anna Maria Island vacation home! The location is excellent, just a few blocks to the white sand beaches of the Gulf of Mexico! This fantastic, three-bedroom, two-bath vacation rental offers everything you need for a relaxing getaway. There are two... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 25
    5 of 5 bubbles (12) Excellent
    Holmes Beach
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Island Hideaway East has been newly renovated for your vacation pleasure! Over 800 square feet of living area boasts a king master and a twin bedroom with a hall bath. The open and spacious living area includes a kitchen with granite countertops and stainless appliances. The kitchen opens onto an... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 14
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 23
    4.5 of 5 bubbles (2) Very good
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    About this property
    Spinnakers Vacation Cottages, Captain's Quarters is surrounded by lush tropical landscaping, close to everything but with a feeling of being tucked away! This lovely vacation rental is located in Holmes Beach and is just 250 steps to the beach! Spinnakers is made up of four cottage-style... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 32
    3 of 5 bubbles (1) Average
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    5 minutes walk to the beach! Totally renovated, furnished 2 bedroom / 2 full bath townhouse. Tile floors, new kitchen & breakfast bar area, granite countertops and stainless steel appliances. Ground floor has additional kitchenette, full bathroom, large living room area. 2nd floor - two large... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 33
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Remodeled cottage with a private, tropically landscaped backyard, heated pool, paver deck, and propane grill! Fig Leaf is just steps to the free Island Trolley and a mere 3 blocks to the gorgeous white sand beaches of Anna Maria. Also in close proximity is the family-friendly Ugly Grouper bar and... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 36
    4.5 of 5 bubbles (3) Very good
    Holmes Beach
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Welcome to Endless Summer - a delightful ground level 4 bedroom, 3 bath home situated on a quiet residential street on Anna Maria Island! Family-friendly amenities abound at this superior vacation getaway, with its very own heated pool in a private setting. Away from busy streets and a mere... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 25
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | 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. Welcome to "Holly Hideaway" located on the northern end of beautiful Anna Maria Island. This lovely two bedroom and two bath vacation rental features all... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 15
    5 of 5 bubbles (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
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    • Shared Garden
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    • Pet-friendly
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    • x
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    • x
    About this property
    Shell Cottage is situated just 200ft away from the beautiful white sandy beach of Anna Maria which is 7 miles long. Set in a quiet leafy lane Shell shares our heated pool with our other 2 cottages and can be rented together or separately. Shell Cottage has a small sofa-bed therefore enabling it to... View all property information
    Location Information
    Anna Maria Island, Florida FL34216
    1 / 28
    Anna Maria
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • x
    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
    Location Information
    Anna Maria, Anna Maria Island 34216
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    1 / 23
    4.5 of 5 bubbles (4) Very good
    Holmes Beach
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
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    • x
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    • x
    About this property
    **SPECIAL** Receive more than $280 off weekly rentals through December 15, 2016! To take advantage of this offer use the promo code CROWS when reserving Crows Nest! -------------------- Part of the Spinnakers Vacation Cottages, Crows Nest is what some have called an adult version of a tree house,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 24
    4 of 5 bubbles (5) Very good
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • Sauna
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    • x
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    • x
    About this property
    Sun Plaza West, located in Holmes Beach on Anna Maria Island, is a fantastic get-away for the beach lover and tennis enthusiast! This two-bedroom, two-bath, end unit condo is located just steps to the white sand beaches of the Gulf of Mexico. This vacation rental features a large master suite with... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 39
    5 of 5 bubbles (2) Excellent
    Anna Maria
    Studio, 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 34216
    1 / 18
    Anna Maria
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    ***Heated Pool and Hot Tub Construction to be completed by June 17, 2017, Stay Tuned for Updated Pictures*** This Cozy 2 Bedroom/1 Bath Cottage is clean, quaint, and only steps to the beach (2 houses to be exact)! It exudes that "Island Feel" from the moment you lay eyes on it! Outfitted with... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 24
    4.5 of 5 bubbles (8) Very good
    Bradenton Beach
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    This beautiful three-bedroom, two-bath vacation rental sits on a tiny slip of land on the south end of Anna Maria Island in the city of Bradenton Beach. Located in Coquina Moorings, a small private condo complex, this end unit accommodates six and offers a heated pool, private boat slips and... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island 34217
    1 / 28
    Holmes Beach
    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.   Close to the Beach, classic, and cute!  Welcome to Little Miss Magic located at beautiful Anna Maria Island on the West Coast of Florida. Beach access is... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 28
    5 of 5 bubbles (2) Excellent
    Anna Maria
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Beautifully remodeled 3 bedroom/2.5 bath home with luxury amenities on the North End of Anna Maria, just 4 houses to Bean Point, one of the quietest beaches on the island, and 2 blocks to the famous Rod & Reel Pier! Private Backyard with Heated Pool, and an open floor plan with vaulted ceilings!... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 24
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Once you open the door to Gulf View 201, you will begin to relax. This two-bedroom, two-bath vacation rental condo will encourage you to have a fabulous vacation on Anna Maria Island. The breathtaking view of the sparkling Gulf of Mexico water through floor to ceiling windows in the open living... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 50
    Holmes Beach
    6 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Villa Chianti is a luxurious Anna Maria Island vacation home in Holmes Beach that boasts one of the largest beach entry pools on the island. The world-famous Old Florida charm of Anna Maria meets modern living in Villa Chianti. With every modern convenience and a high level of attention to detail... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34216
    1 / 40
    Holmes Beach
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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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
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 39
    Anna Maria
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Welcome to the exceptional beach house that is Blue Turtle! This 4 bed/3 bath gem is perfectly positioned on the north end of Anna Maria and will positively provide a picturesque vacation experience. The gorgeous backyard is your private, tropical paradise complete with heated pool and dock to take... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 21
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Located in Holmes Beach on Florida's beautiful Anna Maria Island, Aqua Maria is just steps to the beach. Newly decorated and updated, this two bedroom, two bath vacation rental is inviting and relaxing. Gorgeous furnishings from The Pamaro Shop gives this vacation rental an incredible beachy feel.... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 24
    5 of 5 bubbles (6) Excellent
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Your vacation starts here! Kick back and relax with family and friends in this lovely well-appointed home and you'll take home memories to last a lifetime. With over 1400 square feet of living space, Island Hideaway West boasts three large bedrooms with a king master suite, a queen in the second... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 63
    3 of 5 bubbles (2) Average
    Bradenton Beach
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach. The Anna Maria Island Beach Palms has just been completely updated with a new state of the art ultra high efficiency air conditioning system with all new duct work, 3 new flat... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 24
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Sun-Day West is the picture-perfect name for this two-bedroom, two-bath, elevated duplex. Located in Holmes Beach on Anna Maria Island, this vacation rental features a large, west-facing balcony that allows for plenty of sunshine in the afternoon and shade in the morning for that early cup of... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 23
    4.5 of 5 bubbles (6) Very good
    Holmes Beach
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Escape to Serenity sums it up for this quaint and cozy duplex (with no shared walls). You will feel as if you have landed on your own personal island with this gem of a property. This fantastic, two-bedroom, one-bathroom vacation rental will help you find some serenity. This home boasts an all-new... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 23
    Anna Maria
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Completely remodeled 2 bedroom/2 bath duplex, with a beautiful tropical HEATED pool, just over a block to the beach, and the free island Trolley! There is a King and a Queen bedroom in the North Unit, and a King and Twin Bedroom in the south unit. Both units also have a queen sleeper sofa. Sleeps... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 24
    Bradenton Beach
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A little piece of heaven awaits your arrival! Located in Bradenton Beach on Anna Maria Island at the end of a canal, Heaven Scent offers a daily dose of breathtaking sunrises. A covered front porch, complete with a swing, is the perfect place for a cup of coffee and gorgeous sunrise views.... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 40
    3 of 5 bubbles (1) Average
    Anna Maria
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful ground level 3 bedroom/2.5 bath home, with a quiet north end location only a block to the beach! There is a King in the master with a private patio, a Queen in the second, twin beds in the third, and a queen sleeper sofa in the sunroom (which has blinds for privacy), all accommodating up... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 30
    Anna Maria
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 27
    Holmes Beach
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Welcome to Groovy Guava! This 2 bed/2 bath villa features a private, heated pool in a tropically landscaped setting. The gorgeous white sand beaches and free island trolley are just a 2 minute walk away. Load up the provided beach chairs and beach towels to enjoy a sun-soaked Anna Maria day, and... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | 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.  3 Bedroom, 2.5 Bath (Sleeps 6) - “North Beach Village” 6250 Holmes Boulevard unit 72 in Holmes Beach. Relax in casual luxury and comfort at North Beach... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 123
    5 of 5 bubbles (34) Excellent
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Smoking allowed
    • x
    About this property
    Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 29
    Bradenton Beach
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
    • Hot Tub
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    • Child-friendly
    • x
    • ?
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    • x
    About this property
    2104 Ave A -Private Home 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. This is a cute single family home located only minutes away from the popular BeachHouse Restaraunt (newly renovated), Bay Front Park, Historic Bridge Street, and just 3 blocks from the beach. It features two bedrooms and... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 23
    4.5 of 5 bubbles (7) Very good
    Anna Maria
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal for a vacation getaway! This quaint... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 24
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | 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.   Willow Cottage is a lovely ground level bungalow in Anna Maria just waiting to give you that tropical vacation you dream of and deserve! This private... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 24
    5 of 5 bubbles (1) Excellent
    Anna Maria
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This lovely two bedroom family- and pet-friendly Anna Maria Island vacation rental is just a few houses from the island's white sand beach and azure blue waters of the Gulf of Mexico. Located on the quiet north end of the island in the city of Anna Maria, at 950 square feet, this classic elevated... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 15
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Mar 01 - Apr 28 : Saturday check-in required, Saturday check-out required. May 27 - Apr 19 : Saturday check-in required, Saturday check-out required. Includes swimming pool and partial views of the gulf, and only 1/2 block from the... View all property information
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    Bradenton Beach, Anna Maria Island 34217
    1 / 23
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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.   Windshore is an all new property that showcases designer quality furnishings and is fully equipped with all the most updated features. The brand new... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 30
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Private Outdoor...
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Tropical Paradise on Holmes Beach and ONLY 3 blocks to the beach. Anna Maria Island, noted for its old Florida ambiance, offers this Key West styled home, where you may awaken to greet the dawn sipping coffee on the balcony or swimming in your private pool. The modern interior arrangements add to... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217