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Cottages in Anna Maria Island, FL

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    All 915 Rentals in Anna Maria Island
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    Travellers to Anna Maria Island are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    Anna Maria
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    Anna Maria
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Anna Maria
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Anna Maria
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Sunset Cottage on Rose 710 Rose Street Anna Maria, FL 34216 Sunset Cottage on Rose is a beautiful newly renovated Island home located on the prestigious Northern End of Anna Maria Island! Tucked away on a quiet residential street this wonderful property is your home away from home. With just a... View all property information
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    Anna Maria, Anna Maria Island 34216
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    4.5 of 5 stars (2) Very good
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    Ground level remodeled three bedroom and two bath island vacation rental home just one short block to the best beaches Anna Maria Island has to offer. If relaxation is what you are searching for, then you will find it here! This beach rental home is in a quiet neighborhood in the heart of Holmes... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 / 28
    Anna Maria
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    Villa La Concha 113 Maple Avenue Anna Maria, Fl 34216 Villa La Concha is a stunning brand new elevated and luxury Island home located on the prestigious Northern end of Anna Maria Island. This lovely home is located West of Gulf Drive and just 1 minute stroll down the street from a direct beach... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Anna Maria
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Anna Maria Chateau 612 Fern Street Anna Maria, Fl 34216 Perfect island getaway, nestled at the North end of Anna Maria Island. Anna Maria Chateau, open and spacious, a newly and completely renovated, well equipped 3 bedroom, 2 bath home with vaulted ceilings in the living area and in all... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Anna Maria
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    White Sands 709 North Bay Blvd Anna Maria, Fl 34216 White Sands is a newly renovated beach cottage located on the prestigious Northern end of Anna Maria Island. Offering 3 bedrooms and 2 bathrooms, a new kitchen and a private heated pool this home is ideal for your Island getaway! Lots of... View all property information
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    Anna Maria, Anna Maria Island 34216
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    1 / 27
    Anna Maria
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    Whitecaps 749 Jacaranda Anna Maria, FL 34217 Whitecaps is a luxury tropical island style 5 bedroom, 3.5 bathroom home located at the prestigous north end of Anna Maria Island. This home sits only 1 block in from the Gulf beaches and is only about a 1 minute stroll over to the water. It... View all property information
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    Anna Maria, Anna Maria Island 34216
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    1 / 9
    5 of 5 stars (9) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    About this property
    Recently remodeled island duplex just steps to the pristine Gulf of Mexico beaches of Holmes Beach. This vacation rental has been lovingly remodeled, and furnished with everything you could desire for a trip to our little 'Peace' of paradise. The light and bright interior will allow you to... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    Anna Maria
    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Hidden Oasis 777A North Shore Anna Maria, Fl. 24216 This lovely 1 bedroom, 1 bathroom gulf front hideaway has just been completely renovated from top to bottom! This second level location has a private balcony with large southern views of the beautiful blue waters of the Gulf of Mexico. Part... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Anna Maria
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Bay Bungalow 607 N. Bay Blvd. Anna Maria, Fl. 34216 Brand new heated pool! Bay Bungalow is a newly updated elevated bungalow located on the North end of the island, just across from the famous Rod and Reel Pier and only 2 blocks from Bean Point beach. The custom decoration includes nautical... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
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    • Smoking allowed
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    • x
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    • Elder access
    • x
    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
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    Harbor Breeze 240 South Harbor Drive Holmes Beach, Fl. 34217 A spacious, newly constructed, home with 5 bedrooms and 4.5 bathrooms, Harbor Breeze will offer it all - deluxe private heated pool with hot tub - and the best part is that the pool overlooks the Bay with direct view of the Skyway... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4.5 of 5 stars (4) Very good
    Bradenton Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Dishwasher
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    • Pets allowed
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    • x
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    • Elder access
    • x
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    About this property
    Welcome to the Beach House Resort, located just blocks from downtown Bradenton Beach, Florida on beautiful Anna Maria Island! This Gulf front vacation rental condo is located directly on the beach and features spectacular beach views from every unit. This unit is newly refurbished with top of... View all property information
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    Bradenton Beach, Anna Maria Island 34217
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    Holmes Beach
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • x
    • x
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    About this property
    Island Retreat 4805 2nd Avenue Holmes Beach, FL 34217 Key West meets Anna Maria Island in a dream vacation home. Island Retreat combines the best of both worlds, oozing a traditional south Florida style outside, with shaded balconies and intricate wooden architecture, with unrivalled, modern... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    $216
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    Holmes Beach
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
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    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    About this property
    One bedroom one bath condo located on the poolside. 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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    One bedroom one bath condo located on the poolside. 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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    $190
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    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Very spacious two bedroom Condo with a large living room. Flat Screen TV, fully equipped kitchen with all the appliances. Not far from the beach, and short distance to area shopping. Unit has heated pool, and a relaxing Pool deck area. Main bedroom has a King size bed with a private bathroom and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Anna Maria
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    This Island holiday home with easy access to the Gulf of Mexico and colorful sunsets. Two bedroom and one bath vacation rental in a desirable north end of Anna Maria location. It is also just a flip-flop walk to the pristine gulf beaches. Pet friendly and wireless internet There are so many... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Holmes Beach
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    Bayfront Paradise 238 South Harbor Dr. Holmes Beach, Fl 34217 Bayfront Paradise is an absolutely stunning custom luxury home that is tucked away on a quiet residential street with the most amazing Bay views. As soon as you enter the property you are immediately immersed in the relaxing isle... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Egrets Landing 303 74th St. Unit A Holmes Beach, Fl. 34217 Egrets Landing is a brand new ground level construction with a private heated pool! Offering the best of all that Anna Maria Island has to offer with its central location, you are never too far from white sandy beaches, local cuisine,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    $204
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Sand Palace 215 65th Street Holmes Beach, 34217 Sand Palace is a freshly remodeled 3 bedroom and 2.5 bathroom elevated home with a private heated pool and spa. Only a short 2 minute walk to the Gulf beach, this property offers the convenience of not only its central location but its open... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Beach Isle 304 58th st. Holmes Beach, Fl. 34217 This newly constructed private 2/2 home is perfect for your island vacation getaway! Lounge by your tropical private, heated pool or on our white sandy beaches, the choice is yours with this versatile home! Centrally located to local restaurants... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Anna Maria
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    DIRECT GULF FRONT cottage in City of Anna Maria. This totally remodeled vintage beach cottage is located directly on the beautiful white sand beaches on Anna Maria island. As you can see, the cottage faces west on one of the best rated beaches in the world by several travel magazines. This ground... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Holmes Beach
    6 Bedrooms / 6 Bathrooms / Sleeps 16
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    • Internet Access
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    About this property
    Hemingway House 4103 4th Avenue Holmes Beach, Fl 34217 Hemingway House is a gorgeous, brand new elevated Island house that is tucked away on a quiet residential street and only a short one minute stroll to the Gulf beaches. This 6 bedroom and 6.5 bathroom luxury home is equipped with a private... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • x
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    About this property
    Riki Tiki 110 46th Street Holmes Beach, Fl 34217 Riki Tiki is a beautiful beach house that is only 3 houses away from the stunning Gulf of Mexico. Offering a fantastic location, private heated pool, lots of amenities including a gourmet and fully stocked kitchen and much more! The sleeping... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    $164
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    Holmes Beach
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • x
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    About this property
    Seaside Gardens 460 63rd Street Holmes Beach, Fl 34217 This lovely canal front, ground level, attached bungalow offers fantastic views and amenities! Enjoy the shared deep water dock right off of your backyard, community tennis courts, private ping-pong table, board games and so much more! This... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    SugarSands (La Casa Unit #8) 7316 Gulf Drive Holmes Beach, FL. 34217 Located in the prestigous La Casa Costiera condo complex, you will find SugarSands right beside the crystal blue Gulf of Mexico. It is a truly gorgeous beachfront building nestled right on the edge of the seven miles of... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Bradenton Beach
    2 Bedrooms / 6 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Pets allowed
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    • x
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    • Elder access
    • x
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    About this property
    This property allows for ANY day check-in. Sunset Villa awaits the vacationer in you. Located in this well-kept condo complex directly across front the street from the best beaches on the West coast of Florida. Come for a week or stay a month you will be right where you want to be. Enjoy this... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • x
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    About this property
    It's My Dream 5607 Carissa Street Holmes Beach, Fl. 34217 It's My Dream is a brand new and lovely island-themed private duplex with 3 bedrooms and 2 bathrooms. Equipped with a private heated pool, spa and spacious deck-this home truly represents the best of what Anna Maria Island has to offer.... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • x
    • x
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    About this property
    Beach Dream Cottage 5605 Carissa Street Holmes Beach, Fl. 34217 Beach Dream Cottage is a brand new private duplex that is equipped with 3 bedrooms and 2 bathrooms. This lovely home has a private heated pool, spa and spacious deck-ideal for relaxing in the Florida sun! Just a short 2 minute walk... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Island Paradise #5 3708 Gulf Drive #5 Holmes Beach, Fl 34217 This property is only available for a minimum 1 month rental from January, 2014 through April, 2014 and 2015. Please see approximate monthly rates below (rates do not include any taxes or cleaning fees). Please call our office at... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    About this property
    Villa Portofino 4112 5th Ave. Holmes Beach, FL 34217 Villa Portofino- it defines Anna Maria Island luxury. This upscale 5 bedroom, 3.5 bathroom Mediterranean Villa is only a short 3 minute walk from the beautiful white sand beaches. There is a walk-in heated swimming pool with waterfall.... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 of 5 stars (8) Excellent
    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (8) Make Enquiry
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    • Dishwasher
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    • Pets allowed
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    About this property
    3205 Gulf Drive at Palm Isle Village in Holmes Beach, FL - Anna Maria Island's NEWEST and finest condominium complex offers several fabulous holiday villas all designer decorated and with floor plans maximizing water views. A heated pool is a great place to relax after a day at the beach. Widow... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    About this property
    One bedroom one bath condo located on the poolside. 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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Casa on the Beach 404 South Bay Boulevard Anna Maria, Fl 34216 Newly renovated!- Casa on the Beach is a gorgeous 'Old Florida' styled elevated cottage that faces the Bay with its own private beach area. Enjoy breathtaking views of the water and Skyway Bridge right from the privacy of your own... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    Avalon 2803 Ave E Holmes Beach, Fl. 34217 Wow, if you have looked at the pictures what else is there to say! The views on this fantastic new luxury 4 bedroom, 3.5 bathroom are simply out-of-this-world! Avalon truly has it all- luxury from the word go. Fine travertine marble, custom hard wood,... View all property information
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    Holmes Beach, Anna Maria Island 342177
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    Holmes Beach
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Calypso Cottage 515 42nd St. Holmes Beach, Fl. 34217 Calypso Cottage is a stylish Mediterranean beach villa with all the finishing touches of what you would expect from an exquisite Anna Maria vacation home. Only a 5 minute stroll to the beach, the focal point has to be the brand new elaborate... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 of 5 stars (2) Excellent
    Anna Maria
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Dishwasher
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    About this property
    Welcome to 'My Sister's Beach House' located at 520 Bayview Place on beautiful Anna Maria Island, Florida. This luxurious home has just been all updated and welcomes the vacationers who want to make their time on our beautiful island a wonderful experience. This luxury vacation rental is located... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Mermaids Crossing 207 69th Unit B Holmes Beach, Fl. 34217 Mermaids Crossing is a cute-as-a-button newly renovated, ground level 3 bedroom and 2 bathroom private duplex that offers a private heated pool, lush tropical landscaping, fantastic furnishings and so much more! Centrally located on the... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Mango Bay 417 Clark Dr. Holmes Beach, Fl. 34217 Mango Bay is not your average vacation rental- it is much more. It is a custom built, elevated 4 bedroom, 2 full bathrooms, 2 half bath, private villa with heated pool and deluxe hot tub (it has it's own table built in). It Includes a huge master... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    Mermaids Watch 207 69th St. Unit A Holmes Beach, Fl. 34217 This brand new ground level duplex features 3 bedrooms and 2 baths, a private heated pool with spa and swim up table, and is only a short 2 minute stroll to the Gulf beach. Professionally decorated and outfitted with fine fixtures,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    2 Bedrooms / 3 Bathrooms / Sleeps 4
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    About this property
    Bay Bella Vista 244 S. Harbor Drive Unit 2 Holmes Beach, Fl 34217 BAYFRONT CONDO - This 2 bedroom, 3 bathroom condo is beautifully furnished and features exceptional views of the intracoastal waterway. Enjoy the breathtaking views from the Master bedroom and living room! There is a private... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 of 5 stars (1) Very good
    Anna Maria
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dishwasher
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    • Shared Outdoor Pool...
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    About this property
    This newly remodeled two bedroom duplex is situated halfway between the Gulf of Mexico and the Tampa Bay. Not more than 3 blocks in either direction. It is located on the north end of Anna Maria Island on Magnolia Avenue. A new heated pool was just installed and only can be used by this unit.... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Tropic Dream 5606 Holmes Blvd Holmes Beach, Fl. 34217 This is a newly renovated, ground level 3 bedroom, 2 bathroom home is only a short 2-3 minute walk to the beach. Surrounded by lush tropical landscaping, the home has a private heated pool and plenty of sunshine! It is the South unit of... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    Gulf View Cottage 113 36th St. Holmes Beach, Fl. 34217 Gulf View Cottage has just completed a major renovation and is ready for rental. It has all new bedrooms, bathrooms, kitchen, private heated pool, 2 decks and much more! It is only a short 1 minute stroll over to the beach and there are no... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    Mojito Splash 304 65th St. Holmes Beach, Fl. 34217 This beautiful 5 bedroom, 3.5 bathroom Island style home is perfect for all your vacation needs. It is only a short 2-3 minute walk to the white sand beaches of the Gulf of Mexico. It also is a very short walk to the free trolley stop which... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Holmes Beach
    6 Bedrooms / 5 Bathrooms / Sleeps 16
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    Gulfside Oasis 204 66th St. Holmes Beach, Fl. 34217 This is it- the pinnacle of Anna Maria Island luxury! Gulfside Oasis is a brand new luxury home that combines comfort, class and convenience. Spacious, with 6 bedrooms and 5 full bathrooms, this property is the perfect get-away for larger... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4.5 of 5 stars (2) Very good
    Holmes Beach
    2 Bedrooms / 7 Bathrooms / Sleeps 7
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    • Dishwasher
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    About this property
    Gracious Town Home located at 3701 Gulf Drive, Holmes Beach, Anna Maria Island, FL -- (2) Bed: (2.5) Bath: Accommodates up to (6) people: 1 Queen, 2 Twins & Sleeper Sofa: wirless internet, No smoking: No Pets. Absolutely fabulous two bedroom and two and a half baths in Gulfview Town Houses... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217