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Holiday Rentals in Anna Maria Island, FL

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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 32
    4.5 of 5 stars (23) Very good
    Holmes Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 3 | Quick View
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    1 / 52
    5 of 5 stars (22) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 23
    Bradenton Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    This tropical retreat single family home boasts 1800sq. ft.of living space on the in the Braden River Lakes subdivision. The home is nestled among lush tropical palms and Florida vegetation. The expansive plantings provide privacy and a natural preserve setting in the backyard tropical paradise.... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 33
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    606 hampshire lane, holmes beach fl 34217... Exquisite home on a great extra wide canal across the street from the key royale golf club. Designer furnished with top of the line amenities. 3 king bedrooms with tvs in each, 2 bath and a bright sunroom overlooking the dock, pool and outside sitting... View all property information
    Location Information
    Anna Maria Island, Florida
    1 / 13
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Just steps to a white sand beach, and blue green water. ( Bradenton Beach, across street ) Water view from Master bedroom, and Great room, 1120 square feet . 2 large bedrooms, 2 full bathrooms, living/dining combination room, kitchen, and laundry. plus screened in lanai. 3 level building with... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 25
    5 of 5 stars (14) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Newly decorated 10/15/13. New AC unit 08/10/2014. Nice two bedroom, one bath Condo across the street from the Gulf of Mexico Beach. Very well furnished w/stainless steel appliances. Also WIFI for your enjoyment, cable T.V , bluetooth stereo and free US long distance. Condo has a queen bed in the... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 35
    4.5 of 5 stars (23) Very good
    Bradenton Beach
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Beachfront studio located on Anna Maria Island, Florida in the town of Bradenton Beach. This 550 square foot condo sleeps 2 guests comfortably. This is an all inclusive rental, the 11.5% resort tax and the cleaning charge are INCLUDED in the rent. My coquina beach club studio has been completely... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 17
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    As an artist this private three bedroom and two bath multi-level elevated vacation home has been our family retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll to the Gulf of Mexico and the... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 12
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Old Florida charm in a completely remodeled house only 1 1/2 short blocks to an uncrowded beach. Ours is a 2 bedroom/2 bath home which sleeps 5. It is the larger 1/2 of a duplex house with exclusive use of the solar heated saltwater pool in the privately fenced backyard. A garage separating both... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
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    1 / 36
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; You’ll be relaxing into that vacation frame of mind at first glimpse of this three story, key lime colored vacation home in the center of Holmes Beach. This... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 11
    Bradenton Beach
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This private, vacation home has everything for your vacation needs and comforts. Located in a lovely, quaint, waterfront neighborhood along Sarasota Bay, this entire home underwent a complete transformation remodel spanning almost 2 years from the spring of 2013 thru December 2014. The property... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 27
    5 of 5 stars (2) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Pelican Cove 9 - Condo 2 Bedroom /2 Bath bay side, maximum occupancy of 5 people. Florida's Finest Beach to Bay Resort with a Community poo! Located near the shops and restaurants on Bridge Street, Pelican Cove lures those who appreciate a lively vacation. Start your day with a game of tennis,... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 36
    5 of 5 stars (1) Excellent
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view... View all property information
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    Anna Maria, Anna Maria Island
    1 / 31
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Island Beach Club 21 - Condo 2 Bedroom / 2 Bath gulf front , maximum occupancy of 4 people. Community pool. Gulf Coasts Finest!~ Looking for the ultimate Gulf front luxury vacation? Well, look no further. You will love this second level 2 bedroom/2 bath condo. Newly and completely renovated... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 39
    5 of 5 stars (3) Excellent
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Lazy Lagoon has it all! This remodeled 2 bed/2 bath home is anchored in splendid the north end of Anna Maria on a deep water canal with dock, has its own heated pool and hot tub, and is a short walk to the beach, restaurants and free island trolley. The serene canal-front setting coupled with quiet... View all property information
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    Anna Maria, Anna Maria Island
    1 / 16
    Bradenton Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Key West Style Townhouse with a beautiful Gulf, Beach view in Anna Maria Island. This large townhouse with 3 bedrooms, 3 1/2 baths multi level front unit is the ideal location for family. Overlooking Gulf Drive North located on the West Coast of Florida, Anna Maria Island is situated between the... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 23
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Cayman 204 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 4 people. FALL SPECIAL now through mid December 2016. Weekly rate has been dropped to $700 for the week. Now is the time to find peace and quite in paradise! Come and relax in this very comfortable two bedroom condo.Small complex in the... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 19
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Pelican Cove 11 - Condo 2 Bedroom /2 Bath bay view, maximum occupancy of 4 people. Florida's Finest Beach to Bay Resort with a Community pool! Pelican Cove is a small, private complex with heated pool and spa, tennis court, and large dock for fishing and boating. The shops and restaurants of... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 25
    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Island Beach Club 2 - Condo 2 Bedroom / 1.5 Bath ground level gulf front , maximum occupancy of 4 people. Community pool. Your Ultimate Gulf Front Luxury Vacation! Look no further. You will love this ground level 2 bedroom/1.5 bath condo. This spectacular, brand new Island Beach Club luxury... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
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    1 / 23
    Anna Maria
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    313 Palm Ave - Duplex 2 Bedroom /1 Bathroom , maximum occupancy of 4 people. Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 5 min walk from the beach! Located right in the heart of the village of Anna Maria, not only can you walk to the beach in a matter of seconds,... View all property information
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    Anna Maria, Anna Maria Island
    1 / 13
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Fun and beachy lower duplex with pool on Anna Maria island. Only a block and a half from the beach. Wash the sand off fro the beach with the outdoor shower and foot wash. Play or relax by the pool. Outdoor furniture is perfect for eating or entertaining outside. Lounge furniture is perfect for... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 11
    5 of 5 stars (1) Excellent
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Runaway Bay 115 - Condo 1 Bedroom/ 1 Bath , maximum occupancy of 4 people. Runaway Bay ----Large complex ---right across the street from the beach. Easy beach access. Tastefully decorated 1 bedroom, 1 bath unit with a nice pond view. Relax in the inviting pool, or play a game of tennis,... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 27
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This nicely appointed 2 bedroom, 2 bath ground floor home with Private Pool is located one very short block to the beautiful white sand beaches of Anna Maria Island. Quiet North Holmes Beach location. The home offers a spacious living room, Florida room and fully equipped and nicely appointed... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 33
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Location, location, location. The 3 most important things to consider in a vacation rental. Tucked back on a VERY peaceful setting. Brick patio courtyard and PRIVATE outdoor covered patio set with umbrella. This is a desired ground level end unit in a Key West styled 4 plex. Nestled under several... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 25
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    20771st Beach Villa -Duplex 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. The perfect spot for the budget-conscious, beach-loving vacationer! This comfortable and clean 2 bedroom/2 bath elevated duplex is only 200 yards from the fabulous white sand beach and crystal-clear waters of the Gulf... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 16
    Holmes Beach
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    Located in Holmes Beach, on Anna Maria island. This one bedroom two bath unit is a full size apartment with full size kitchen all appliances dishwasher, stove full size refrigerator, living area, dinning area and a separate bedroom has 2 full size beds. Its just steps to the beach. Covered parking.... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 11
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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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    Bradenton Beach, Anna Maria Island
    1 / 26
    5 of 5 stars (2) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Bradenton Beach Club 238 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 7 people. SEPTEMBER SPECIAL --$1000 +++ PER WEEK. CALL TODAY TO BOOK YOUR VACATION! Beautiful Bradenton Beach club is a luxury complex, featuring two heated pools, spa and bayside gazebo, with a grill out area. Condo 2... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 21
    4.5 of 5 stars (4) Very good
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    SPECIAL RATE OF 1300 IF YOU BOOK AND STAY FROM NOW TO DECEMBER 2016..EXCLUDES HOLIDAY WEEKS. Coquina Moorings 201 - Condo 2 Bedroom/ 2 Bath with Den/3rd room , maximum occupancy of 6 people. This beautifully landscaped bay front complex has lots to offer. It features a heated pool directly on... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 21
    Holmes Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This wonderful vacation home is located in the quiet and peaceful neighborhood of Holmes Beach on beautiful Anna Maria Island within walking distance to the beaches. The private backyard features a heated private pool, full sized BBQ, cozy outdoor seating and an outdoor dining table. For... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 10
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    2206 Ave. B - Private Bungalow 2 Bedroom / 1 Bath, maximum occupancy of 4 people. Quaint Island bungalow In a friendly neighborhood in Bradenton Beach where the water is sparkling blue and the beaches are beautiful. Enjoy bicycling with a bike available for your use and then cool off with the... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 27
    4 of 5 stars (1) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Make your stay in Florida fun and easy! This 2 Bedroom, 2 Bath condo is direct beachfront with wide open views up and down the coast. The condo is on the top floor (6th) of the building and is completely furnished with a dining table that seats 6 – 8, sofa and loveseat, coffee and end tables, flat... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 36
    Holmes Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 4 Bedroom, 4 Bath (Sleeps 10) - “Bimini Bay” 4807 2nd Avenue in Holmes Beach. The perfect holiday getaway for family and friends, “Bimini Bay” is a... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 9
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Runaway Bay 278 - Condo 2 Bedroom/ 2 Bath ), maximum occupancy of 4 people. Runaway Bay ----Large complex ---right across the street from the beach. Easy beach access. Runaway Bay ----Large complex ---right across the street from the beach. Easy beach access. Largest heated pool on the... View all property information
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    Bradenton Beach, Anna Maria Island
    1 / 26
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    520 67th - Private canal home 2 Bedroom / 2 Bath with private pool , maximum occupancy of 4 people. Fabulous canal-front two bedroom and two bathroom home with all the comforts of home. Filled with lots of sitting areas to read a book or totally relax looking at the water view. Located on a quiet... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 23
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Plum Cottage 324 is professionally decorated with a laidback island flavor, and offers everything you'll desire for a truly memorable vacation! This single... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 40
    Holmes Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Relax in absolute style in this immaculate 4 bedroom, 4.5 bath home. Coastal to the core with its bright, airy, sea-side inspired design and finishes. Every detail, a perfect one, to make you feel right at home and, of course, right at the beach! The front entry spills into the spacious great room... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 38
    5 of 5 stars (5) Excellent
    Holmes Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • x
    About this property
    Beautifully furnished 4 bedroom/3.5 bath home just a block to the beach! Large greatroom layout with four separate balconies, high ceilings, and tropical hardwood floors throughout. Master Suite on the main floor has large walk-in closet and ensuite bathroom with Jacuzzi soaker tub and separate... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    Anna Maria
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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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.; (3) Bedroom, (3) Bath (Sleeps 8) – “Fish House” – 231 Oak Avenue in Anna Maria. For the perfect Anna Maria Island vacation, escape to the adorably... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 34
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • x
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    • x
    About this property
    Three bedroom, two bath totally redone home with gorgeously landscaped backyard and heated pool! Only houses to the Gulf of Mexico and a beautiful white sand stretch of beach! This home has been updated with Mexican tile, granite countertops, and stainless kitchen! King-sized master bedroom, second... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 11
    5 of 5 stars (3) Excellent
    Holmes Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    • x
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    • x
    About this property
    7310 Holmes - Duplex 1 Bedroom / 1 Bath , maximum occupancy of 4 people. Fun in the Sun!~ Ground level duplex that's fun and adorable. This one bedroom, one bath unit has a private outdoor patio area. This unit has recently been renovated and is perfect for a couple with visiting guests.... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    5 of 5 stars (8) Excellent
    Holmes Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This vacation rental has been completely refurbished, with tile floors and ceiling fans throughout and a beautiful heated pool. Centrally located on Anna Maria Island, Twin Villa is a short two block walk to the beach. The well-appointed kitchen is equipped with a vegetable sink, stainless... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 20
    5 of 5 stars (3) Excellent
    Anna Maria
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    • x
    About this property
    Great 1 Bedroom/1 Bath remodeled cottage on the quiet North End with outdoor patio, ceramic tile throughout, and granite countertops. 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... View all property information
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    Anna Maria, Anna Maria Island
    1 / 13
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Outdoor Dining Area
    • Wi-Fi
    • Porch
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    • x
    • x
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    • x
    About this property
    This furnished, first floor unit is a recently remodeled, two bedroom, one bath vacation condo in a friendly, 55 and older community in Bradenton Beach. Off street parking is included adjacent to the unit. The kitchen is fully equipped and has a dish washer. Enclosed, furnished back porch. Basic TV... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 23
    4.5 of 5 stars (3) Very good
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • x
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    • x
    About this property
    Pelican Cove 1 - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 6 people. Florida's Finest Beach to Bay Resort with a Community pool! Located near the shops and restaurants on Bridge Street, Pelican Cove lures those who appreciate a lively vacation. Start your day with a game of... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 24
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    109 Willow Casa Nana - Cottage 2 Bedroom / 2 Bath , maximum occupancy of 6 people. Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building happy summer memories right in this spot, and they... View all property information
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    Anna Maria, Anna Maria Island
    1 / 5
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    • x
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    • x
    About this property
    Our largest cottage, sleeps 4, great bay views. Tastefully furnished in a shabby chic beach motive. This room features all the comforts of homes. Just a two minute walk to Bradenton Beach and world famous Bridge Street where you will find restaurants, shopping and nightlife. Bring your fishing pole... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island
    1 / 27
    5 of 5 stars (3) Excellent
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 15
    4.5 of 5 stars (8) Very good
    Bradenton Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Waterfront
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Washer
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Gorgeous 3 bedroom town home, with view of the beach. Miles of white sandy beaches, close to shops, restaurants, and all types of water sport activities. Located in the heart of Bradenton Beach, this home has all the amenities, two car garage for private parking, full equipped kitchen, flat screen... View all property information
    Location Information
    Bradenton Beach, Anna Maria Island