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Holiday Rentals in Anna Maria Island, FL

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    695 Holiday Rentals in Anna Maria Island
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    €147
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    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Come relax and enjoy your beach vacation at The Dolphin Club! 2 bedrooms and 1 bathroom, the master bedroom has a queen bed and the other has 2 twin beds. There is also a sleeper couch in the living room which can sleep 2 people. Fully air conditioned. Includes covered parking and outdoor deck with... View all property information
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    4.5 of 5 stars (4) Very good
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Bridgeport Condo 204, located at 501 Gulf Drive North in Bradenton Beach is a spacious two bedroom, two-bath condo with an elevator, undercover parking and large heated pool. You can enjoy Gulf views from the lanai. Bridgeport Condo is a great Bradenton Beach rental property!This beautiful unit... View all property information
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    €1,500
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    About this property
    Enjoy amazing sunsets from the screened lanai of this recently remodeled 2 bedroom, 2 bath Gulf front tastefully furnished to comfortably fit 4 people. This condo has cable TV in the master bedroom and the living room, towels and linens, kitchen items, cooking utensils and beach chairs. Enjoy a dip... View all property information
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    €134
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    About this property
    Come relax and enjoy your beach vacation at The Cast Away! Located conveniently across from the Manatee Public Beach and the Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and living room are included for your... View all property information
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    €282
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    1 / 12
    Bradenton Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    About this property
    Please note these Check-in Day Requirements for this property: Jun 24 - Jun 30 : Wednesday, Thursday, Friday, Saturday, Sunday, Monday and Tuesday check-out required.; Jul 26 - Aug 01 : Sunday, Monday, Tuesday, Wednesday, Thursday, Friday and Saturday check-out required.; Nov 22 - Nov 28 : Sunday,... View all property information
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    €1,111
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    1 / 5
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Lovely 2 bedroom, 1.5 bath Bay front home with boat/fishing dock. Beautiful views of the Bay. Located on a quiet street just one block to the beach. Located on Ana Maria Island. View all property information
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    €972
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    1 / 21
    Holmes Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Sunbow Bay Condominium 1B located at 3701 East Bay Drive in Holmes Beach has everything you could need or want for a memorable vacation. Conveniently close to shopping and restaurants yet out of the way and quiet. Sunbow Bay offers two heated pools, tennis courts, undercover parking and every... View all property information
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    €98
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    1 / 10
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    For your next Florida Gulf beach vacation, come enjoy the fully furnished 2 bedroom, 2 bath condo at Runaway Bay resort complex on beautiful Anna Maria Island. Runaway Bay. Unit 127 includes a fully equipped kitchen, washer/dryer in the unit, DVD/CD player and cable TV in all rooms. This is a... View all property information
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    €139
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    1 / 24
    Holmes Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This newly remodeled Florida gem backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably priced, this quaint 3 bedroom, 1 bath cottage has a spacious backyard equipped with a pool, hammock, patio furniture, grill, brick fireplace, and picket fencing,... View all property information
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    €130
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    About this property
    Enjoy this bright and cheery Island Beach House Sun Porch Apartment decorated with great island ambiance! Watch the island time go by from the large Sun Porch including the pelicans flying overhead and watching the stars after a fun day at the beach. Whether it’s a sun and fun filled day at the... View all property information
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    €231
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    About this property
    Special Offer April 11-May 1 $1650.00 all-inclusive per week. Save $467.00. 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 condo is located with-in walking distance of Anna Maria Island's best... View all property information
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located in the heart of Anna Maria Island in the sun-drenched community of Holmes Beach is “Seacrest” where you can enjoy island living at its best in this affordable island vacation destination. This roomy 2 bedroom condo is a recently updated and well maintained unit with covered parking & a... View all property information
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    €440
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    1 / 22
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sarasota bay fond , few steps short walk to Gulf of Mexico white sandy beach, private dock and pool with hot tub , Free byk and kykak... View all property information
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    €648
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    About this property
    West Bay Cove is a great location for taking advantage of everything that Anna Maria Island has to offer. Only a block from the public beach area, close to the grocery store, several shops and at a trolley stop, this condo will meet all of your needs without a car. The grounds are well cared for... View all property information
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    €787
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    About this property
    This villa is quaint and adorable tucked in a quiet neighborhood just 9 houses from the Gulf of Mexico and white sandy north end Anna Maria Island beaches. Step outside your door and stroll down the street in 1 minute or less to the quaint shops and cafes along Pine Ave. Walk to everything the... View all property information
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    €185
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    About this property
    Two Bedroom/2bath Home in Bradenton Beach Sleeps 6. This is a two bedroom/2bath home in Bradenton beach, with washer/dryer, new kitchen (granite counters), big screen/WiFi, great fishing on your own dock, on a quiet street, five minute walk to bridge street shopping area, two minute walk to the... View all property information
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    €713
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    3 of 5 stars (2) Average
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Hammock Haven is a wonderful two bedroom two bath home located at 2702 Avenue C in Holmes Beach. This two story beach get away has a distant gulf view and a peek at the bay. Hammock Haven is close to dining, beach, trolley, and the bay. Stroll the beaches, fish the bay, and explore the many... View all property information
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    €409
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    1 / 25
    Overview
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    • Gym
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    About this property
    Island Paradise is just that- the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any better than this. It is like you are sitting on the deck of a cruise... View all property information
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    €79
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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 of Mexico! If rising vacation rental prices have you worried, this is your... View all property information
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    1 / 25
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 invite you to create some of your own treasured moments on your next visit to Anna Maria.... View all property information
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    About this property
    Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 6 to... View all property information
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    €2,754
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    1 / 22
    4.5 of 5 stars (6) Very good
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    L’Plage Condominium #3 located at 6420 Gulf Drive in the preferred northern end of Holmes Beach is a spectacular four bedroom, three bath Gulf front unit with a glorious beachside swimming pool and spa. There is even a BBQ area onsite for your use! L’Plage Condominium features a security gated... View all property information
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    €1,111
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Suitable for children
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    About this property
    Located on Anna Maria Island, this duplex is in a great location for all that the island has to offer. It is close to a boat ramp, to the town tennis courts and a short walk to the beach. This property offers two bedrooms and two baths with a comfortable living, dining and kitchen area. All that... View all property information
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    About this property
    With Bradenton Beach Club (Gulf Breeze), you will get exactly what the name says - outstanding breezes right off the crystal blue waters of the Gulf of Mexico. This luxury 3 bedroom, 2.5 bathroom water front condo has it all. Crown moldings, elegant furniture and fixtures, beautiful hardwood floors... View all property information
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    €422
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    1 / 27
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    You'll be hard-pressed to find something more luxurious than this beautiful three bedroom, two-and-a-half bath unit at the prestigious La Casa Costiera. These high-end condominiums are in demand year-round...take one step inside and you'll immediately know why. You'll find all the luxury touches,... View all property information
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    €139
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    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Relax in the casual comfort of an island paradise, and have a true Old Florida experience on Anna Maria Island, where riding bikes is the preferred way to travel and indulging in the simple pleasures of life - sun, beach, scuba dive, Snorkel and relaxation are the favorite past times. Enjoy and... View all property information
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    €1,750
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    1 / 22
    3 of 5 stars (1) Average
    Bradenton Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    The Bay Delight is just that; a delight! This bay side four bedroom, four bath duplex, located at 2500 Avenue B in Bradenton Beach offers every conceivable amenity to make your stay here a pleasant and comfortable one. Each unit offers full size washer and dryer, microwave and dishwasher.... View all property information
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    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. 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... View all property information
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    €449
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    1 / 19
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    La Plage 2 is Island luxury at it's finest. An exquisite example of Mediterranean architecture nestled right on the sands of the Gulf of Mexico, this beachfront enclave will exceed all your expectations. Relax in the tropical splendor of this ultra-luxurious beachfront property on Anna Maria Island... View all property information
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    €93
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    About this property
    Very contemporay condo, just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise. The unit is inspiring and gives you a laid back feeling immediately after entering. A huge pool with lounges and sun umbrellas are waiting... View all property information
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    • x
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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
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    1 / 27
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Smoking allowed
    • Suitable for children
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    About this property
    Seaside Beach House #205 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a heated pool. It's one of the nicest complexes on Anna Maria Island. This 'hidden away' property is located on a quiet side street in the northern end of Holmes Beach. It offers a heated pool,... View all property information
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    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Balcony
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    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    About this property
    La Plage Unit 9 is the cream of the crop. Direct Gulf Front, high-floor views make this one of the most spectacular luxury condo's on all of Anna Maria Island. What you get on the inside is no less outstanding. The deep cherry wood island style furniture is the finest around. Granite countertops,... View all property information
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    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Suitable for children
    • 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
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • 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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    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    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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    4.5 of 5 stars (2) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
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    • Pets allowed
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    • Suitable for children
    • ?
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    • Elder access
    • ?
    • ?
    About this property
    Playa Encantada 112 is a gorgeous two bedroom, two bath direct Gulf front complex, located at 6006 Gulf Drive in Holmes Beach. This popular complex features an elevator, heated pool, jacuzzi, 2 tennis courts and shuffle board. The open balcony gives you a view of the gulf.The living room... View all property information
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    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • 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
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    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
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    • Waterfront
    • 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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Dryer
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    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
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    • Elder access
    • x
    About this property
    Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 6 to... View all property information
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    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Coquina Breeze 1107 Gulf Drive South Bradenton Beach, FL 34217 Spectacular Gulf views from every room of this private 2 bedroom 2.5 bath home. Located across from the Gulf of Mexico in Bradenton Beach. Coquina Breeze offers an open living room and European kitchen decks on each floor perfect... View all property information
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    • x
    • x
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    • Elder access
    • x
    About this property
    Special Offer April 25-May 2 $1100.00 all-inclusive. Save $1017.00. Anna Maria Island is not a place you go to the beach. When you are on Anna Maria Island you are at the beach. The Anna Maria Island 'Beach Paradise Condo' is located on Holmes Beach directly in the middle of Anna Maria Island... View all property information
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    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    Gulf / Dolphin Views! 1BR/1BA Villa (villa C) Centrally Located, Walk to All Location! Watch the frequently seen Dolphins from the beach just across the street... Stay here (or rent more villas) for your beach wedding or family reunions. An hour or so before the sunsets, fire up the large grill... View all property information
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    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    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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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    Special Offer April 25-May 2 $1100.00 all-inclusive. Save $1017.00. 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 Breeze is a beautiful two bedroom, one bathroom condo that has just been completely... View all property information
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    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    2 bedroom/2 bath Condo in the heart of the island, and just across the street to the beach. Great location with trolley stop close by. This complex has everything you need for a great vacation. Sleeps up to 4. 1080 Sq. ft. 1801 Gulf Drive N, Bradenton Beach. 2 Bedroom/2 Bath Condo With Heated... View all property information
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