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Anna Maria Cottages

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    Travellers to Anna Maria are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 38
    4.5 of 5 stars (6) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    5 of 5 stars (14) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    5 of 5 stars (13) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    1 / 23
    5 of 5 stars (4) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    We call this home 'A Time Out' cottage and you will definitely say, 'We deserve a time out at this place!' This completely remodeled private home on Anna Maria Island's north end features four bedrooms, two baths and the most wonderful tropical and lush pool and patio area! On the main level of... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 7 April 2015
    This special house is located perfectly away from the hustle and bustle, but at the same time everything is easily accessible. The beautiful beach is just a short stroll, and...
    5 of 5 stars Reviewed 20 February 2014
    When we walked into this adorable cottage, we couldn't believe our eyes. This place is too cute for words! It is the kind of rental you dream about with clean bathrooms...
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 5
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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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    Anna Maria, Anna Maria Island 34216
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    1 / 21
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    The Beach House 9308 Gulf Drive Anna Maria, Fl. 34216 Totally updated 3 bedroom 2.5 bath elevated home just six houses from the Gulf of Mexico. French doors and sliders open to your covered wrap-around porches. Listen to the sounds of rustling palms and embrace the gentle gulf breezes while... View all property information
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    Anna Maria, Anna Maria Island 34216
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    1 / 18
    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • 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.. 708... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 31 December 2014
    BLN is very well located in the quieter northern part of the island. It is just a very short walk from the beach and Ginny and Jane Es. Likewise, a short walk in the opposite...
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    1 / 39
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    1 / 24
    4.5 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
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    • Grill
    • Satellite TV
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    • Waterfront
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    With its luscious landscaping, eclectic look and colorful Key-West style, Simpatico could be right out of Coastal Living Magazine. This bungalow is perfect for the ideal secluded island vacation! Located on the north end of Anna Maria Island, this canal home, with a boat dock and kayaks,... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 11 January 2015
    My husband and I and another couple stayed here for one week in December. This was our first stay on the island and we would definitely go back. We have rented homes all over...
    4 of 5 stars Reviewed 29 July 2014
    The entire grounds and unit are artfully decorated with many vignettes located throughout. Very quiet neighborhood but located within easy walking or biking distance of many shops...
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    1 / 19
    5 of 5 stars (7) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
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    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower and comfortable furnishings. The... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 13 November 2014
    The weather was nice several of the days and we really enjoyed less people than we encounter in July. Lots of beach walks and bike rides. My only issues were the dirty rug in...
    5 of 5 stars Reviewed 8 August 2014
    great home, the owners have thought of every mortal thing.. would def stay again and have also recommmended already to friends of mine
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    1 / 22
    4.5 of 5 stars (5) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 14
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    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
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    About this property
    The Golden Dolphin, located at 801 North Shore Drive in Anna Maria, is the ultimate in beach front luxury. This executive level gulf front home has a tropical heated pool with waterfalls, four bedrooms, a library, three and one half baths a gourmet kitchen and much more. It was custom built with... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 13 July 2014
    Great location, great size for multiple families. impressive kitchen and great for preparing large breakfasts/dinners; Master Suite very impressive and the showers where awesome...
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    $422
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    1 / 39
    5 of 5 stars (2) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 11
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    • Air Conditioning
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    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
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    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    When you 'have anna maria' on your mind, you'll want 'hav'anna hideaway' for your vacation home. This newly constructed 4 bedroom, 4 bath home is located just one short block to the beautiful and sparkling gulf beach. The main floor of the home consists of an open concept living room, kitchen with... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $579
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    1 / 29
    4.5 of 5 stars (4) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier.... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 29 January 2015
    Flawless! Cherryfish, a tropical hideaway I never want to leave! The landscaping is unsurpassed providing a private tropical oasis retreat. The home itself is so fresh with...
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    $137
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    1 / 20
    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 20 January 2014
    We were very pleased with our stay at Snails Pace. Not being familiar with the area and booking online, one is never quite sure what to expect. The location was great, just a...
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    $246
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    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Limelight 771 Jacaranda Rd. Anna Maria, Fl. 34216 Limelight is a gorgeous newly renovated home, inside and out, located on the prestigious North End of Anna Maria Island. Only a brisk 3 minute walk away from the sandy white beaches, this home offers everything you are looking for in an Island... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 11 January 2015
    We loved the location and the house was beautiful and well equipped. It was a perfect place for us to vacation with our three adult children. The kitchen was top notch with...
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    $380
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    1 / 23
    5 of 5 stars (2) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just around the corner from the Rod & Reel Pier, Bayfront Park, and just a couple of blocks to Fabulous Bean Point Beaches and Sunsets. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor lounging... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $295
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    1 / 25
    5 of 5 stars (2) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Great Ground Level 3 Bedroom/2 Bath Home with a Heated Pool located in the quiet north end and just 3 houses to the beach!! King-Sized master bedroom with TV, Queen in the 2nd Bedroom with TV, and Twins in the Third with TV. Cable TV, DVD, and Flat Screen TV in Living Room. High speed Internet,... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    1 / 28
    5 of 5 stars (2) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Located four houses (2 min stroll) from Anna Maria's sugary beach, 'Cozy Cottage' is the ultimate retreat for relaxation and reconnecting with family or friends. Nestled on Anna Maria's cherished North End, this luxurious home features (3) bedrooms and (3) baths - two bedrooms have en-suite... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 22 December 2013
    Anna Maria Island is one of the nicest, most laid-back islands I have ever visited, and Cozy Cottage was a wonderful home that held our family of five very well. Everything was...
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    1 / 24
    5 of 5 stars (7) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    This two-bedroom, two-bath vacation rental is located on the quiet north end of Anna Maria Island. Whispering Pines is just three houses from one of the most beautiful beach accesses on the island. This classic 1920's beach cottage has been lovingly restored. The original wood molding, fireplace,... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 3 November 2014
    We had the most wonderful stay at Whispering Pines, a beautiful cottage on Anna Maria Island. It couldn't have been more perfect. My parents, my two 12 year-olds and I thoroughly...
    5 of 5 stars Reviewed 28 August 2014
    Whispering Pines is an updated and classic Florida home. We traveled with one young child and we all had more than enough space to relax. The beautiful shores of the beach are...
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Las Palmas 212 Palm Avenue Anna Maria, Fl. 34216 North-end location just a few minutes walk to Pine Ave and Gulf beaches! This lovely 3 bedroom 2 bath elevated home with private heated pool is situated in the heart of the island, centrally located to everything fun. Comfortable and charming with... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $615
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    1 / 26
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    Cayman Bay 505 Magnolia Ave. Anna Maria, Fl. 34216 Cayman Bay may well be one of the most exquisite private homes available for rent on all of Anna Maria Island. This 4 bedroom/4 bathroom 5300 sq. ft. custom home has all the fine touches and professional craftsmanship one would expect in a... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 19 August 2014
    We stayed here for two weeks this past August. This was our second trip to AMI - such a lovely place. This house was perfect for us. It is very spacious. All the bedrooms are...
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    1 / 33
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $210
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    1 / 23
    4.5 of 5 stars (8) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Location, location, location. Welcome to the quaint and quiet north end of Anna Maria Island! This classic AMI elevated, open floor plan vacation rental boasts three bedrooms and two baths with plenty of room for a large family or group to spread out and relax! Two queen-size beds, a full-size... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 17 May 2015
    Fabulous location on the beautiful north end of Anna Maria Island. Lovely days starting with a walk to the Gulf. Back to Ginny and Jane E's for brunch. A swim in the pool followed...
    5 of 5 stars Reviewed 8 May 2015
    We had a lovely trip to AMI!! This quaint house included all amenities-including an ample supply of towels (both bath and beach), pillows, and bedding...the heated pool and hot...
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    $157
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    1 / 23
    5 of 5 stars (2) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Your time on Anna Maria Island should be perfectly charming in this classic beach-style cottage perfectly located on the west side of Gulf Drive in the city of Anna Maria. Only steps away from the azure blue waters of the Gulf of Mexico, this unique vacation rental boasts two very large bedrooms... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 18 May 2015
    This is a gem of a place. Location wise, it's tough to beat - a short stroll to the beach, and maybe 5-10 minute walk to the Sandbar restaurant, where you can dine on the beach...
    5 of 5 stars Reviewed 12 November 2014
    On entering the cottage, the screened porch was a perfect cool place to relax in the evening with a drink or to take morning coffee and watch Anna Maria Island come to...
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    $338
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    4 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    Tarpon Pointe 306 Tarpon St. Anna Maria, Fl. 34216 Tarpon Pointe is a newly remodeled property on the exclusive Northern-End of Anna Maria Island! This gorgeous private home embodies all of the best that the Island has to offer including a private heated pool, a dock, several porches,... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    From
    $149
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    1 / 17
    4.5 of 5 stars (4) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    3 of 5 stars Reviewed 18 August 2014
    The location is great, with the bayside on the property along with the pool and the beach just across the street. Our biggest problem was the cell phone signal (VERY LOW) and the...
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    $430
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    1 / 26
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Seaside 851 N. Shore Dr. Anna Maria, Fl. 34216 Seaside is a private, luxury home located on the very northern tip of Anna Maria Island. It looks directly at the Skyway Bridge, Egmont Key and Downtown St. Petersburg- you will not find a more breathtaking view anywhere on the island. The home... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 20 April 2015
    I had never been to Anna Maria Island before, and the rental agent said I would fall in love with it on our first trip; she was so right. That island, with its crystal clear blue...
    5 of 5 stars Reviewed 29 October 2014
    What a wonderful vacation rental!! We had a little birthday party with family and friends and this place had it all! I got so many compliments that I had to let you know. The...
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    4.5 of 5 stars (15) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Grill
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    • Waterfront
    • Water Views
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    • Pets allowed
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    About this property
    The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and soak in the unbelievable views of the Gulf of... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 11 March 2015
    What an amazing spot on the beach. House comfortable &,nautical. Therapy sweeping the pine needles and cones off deck. Bean Point great shelling spot, get there early. South of...
    3 of 5 stars Reviewed 23 August 2014
    The views and the location of this house were simply amazing. The beach is clean, the sand is soft and white and the beach is very wide. There were a lot of sea turtle nests...
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    4 of 5 stars (18) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Grill
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    • Waterfront
    • Water Views
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    • Pets allowed
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    About this property
    The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home!This spacious and charming two bedroom, two bath Gulf... View all property information
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    Anna Maria, Anna Maria Island 34216
    3 of 5 stars Reviewed 24 March 2015
    We were quite pleased when we saw the exterior of the house - very attractive. When we walked in, the house was clean and presented well. There were two of us - college...
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    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
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    Anna Maria, Anna Maria Island 34216
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Southern Breeze #1 607 Fern Street #1 Anna Maria, Fl. 34216 ISLAND 6-PLEX - Newly renovated top to bottom June 2013! These are 2 bedroom, 1 bath ground level units located at the tip of Anna Maria Island just steps from the Bay. Heated pool with nicely landscaped surroundings. Each is... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 21 August 2014
    Amei conhecer a ilha Anna Maria! tanto que estou pretendendo voltar no próximo ano para passar pelo menos um mês inteiro! Alugamos essa casa pela internet com poucos dias de...
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    4.5 of 5 stars (2) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Whispering Winds 210 Sycamore Avenue Anna Maria, Fl 34216 Key West style 4 bedroom, 2 bath home just a short walk from the Gulf of Mexico. This home offers private heated pool, three covered decks overlooking pool, BBQ grill, two car garage, cathedral ceilings, tile, carpet, open floor plan... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 4 October 2014
    You can look at the photos - the house is every bit as good as the description. Everything worked, there were no problems at all with the property. We called Anna Maria Vacations...
    5 of 5 stars Reviewed 13 May 2014
    We stayed at Whisper Winds,3 houses to the wonderful White Sand... Great house with 4 bdrm ,heated pool, great location with plenty of room for Family Vacation.. This is our 2nd...
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    4 of 5 stars (1) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    NORTH SHORE VILLA 904 North Shore Drive Anna Maria Welcome to North Shore Villa. This luxury Key West style home has it all. Expansive bay views, private heated pool, extra large master suite with a double shower and Jacuzzi tub, fresh and modern decor, two large balconies, indoor sitting area... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 5 January 2015
    In August I reserved N. Shore house for 2 weeks - Our family's Christmas- 6 adults. Final deposit due early December. The Home is as described-- very beautiful, casual feel...
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    4.5 of 5 stars (12) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Grill
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    • Shared Outdoor Pool...
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    About this property
    The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains... View all property information
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    Anna Maria, Anna Maria Island 34216
    2 of 5 stars Reviewed 13 January 2015
    clean and nice location. the appliances are out dated as the decor and linens. both queen mattresses where so uncomfortable my spouse and i slept in separate beds.the kitchen is...
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    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    Whispering Whale Retreat 505 Spring Avenue, Anna Maria, Fl 34216 Whispering Whale Retreat is a lovely brand new elevated home with 4 bedrooms and 2 bathrooms. Located on the prestigious Northern end of Anna Maria Island this versatile home incorporates the best of all that Anna Maria Island... View all property information
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    Anna Maria, Anna Maria Island 34216
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Satellite TV
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    • Pets allowed
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    About this property
    Canal Place is a restored three bedroom, three bath Old Florida island home with a pool and hot tub; neutral and relaxing decor with a spacious living room and just a short stroll to the white sand beaches if Anna Maria. Direct waterfront with beautiful canal views. Sleeps upto 8 people. Amenities... View all property information
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    Anna Maria, Anna Maria Island 34217
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    3.5 of 5 stars (4) Average
    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Air Conditioning
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    • Dryer
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    • Pets allowed
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    About this property
    This 3 bedroom/2 bath beachy home has views of the gulf from all but 1 bedroom. It has a 600 sq.ft. deck. The sand is sugary white and this is a private beach, but if you want some action, you can walk to some of the nicest restaurants on the water, or drive 5 or 6 minutes into town. I have had... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 17 April 2015
    We took our family vacation here which was the first time we had rented a beach house for a week and it was absolutely awesome. From the location to the space to the amazing view...
    4 of 5 stars Reviewed 21 January 2015
    Hell yes, I will return to this house! After renting several different homes directly on the beach of Anna Maria for over forty years, I would recommend this house to all of my...
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    3 of 5 stars (1) Average
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    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
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    Anna Maria, Anna Maria Island 34216
    3 of 5 stars Reviewed 1 July 2014
    We had a great time on Anna Maria with our two college-aged sons. This house is very nicely located, and the pool is wonderful. The home was spacious and comfortable for four...
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    2 of 5 stars (1) Poor
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Wi-Fi
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    About this property
    Enjoy your vacation in this charming, one-bedroom, one-bath original house just six houses away from the white sand beaches of Anna Maria Island and sparkling waters of the Gulf of Mexico. Flamingo House is perfect for anyone who needs a quick weekend getaway or an extended stay! Located in Anna... View all property information
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    Anna Maria, Anna Maria Island 34216
    2 of 5 stars Reviewed 11 April 2015
    Very good: the house is close to a beautiful beach Poor: the house is too close to the noisy street; no place to sit outside; terrible smell of humidity inside; windows dirty...
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Sundown South 300 N. Shore Unit A Anna Maria, Fl. 34216 This is a one of a kind brand new construction on Anna Maria Island. Sundown South has 4 bedrooms and 3 full baths and a private heated pool. Located on a beautiful lake on the prestigious North Shore Drive and only a very short walk to... View all property information
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    Anna Maria, Anna Maria Island 34216
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    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    About this property
    The Big Yellow House on Pine 104 Pine Avenue Anna Maria Fl. 34216 This home is one of a handful of very select rental properties on the island- direct Gulf front with a private heated pool! It has all the perfect ingredients for a wonderful vacation. Enjoy your front row seat to spectacular... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Cabana Breeze 511 Spring Avenue Anna Maria Island, Fl 34217 Cabana Breeze is a newly and completely renovated 4 bedroom 2 bathroom home with multiple outdoor shaded living areas, a large lot, and a brand new custom pool and pool-side cabana. This gorgeous home is located on the prestigious... View all property information
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    Anna Maria, Anna Maria Island 34216
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Casa Allegria is just perfect! Beautiful cool beachy colors throughout and only a short walk from the beach. This spacious 3 bedroom, 2 bath ground level home is located in the most sought after area on Anna Maria Island! Close to Pine Avenue, trolley stops, and the SandBar Restaurant. Come and... View all property information
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    Anna Maria, Anna Maria Island 34216
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    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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    5 Bedrooms / 3 Bathrooms / Sleeps 15
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    Lighthouse Lagoon 508 Spring Avenue Anna Maria, Fl. 34216 Lighthouse Lagoon is a beautifully updated 5 bedroom, 3 bathroom Island home located on Spring Street on the North-end of Anna Maria Island. The rear of the house backs up to outstanding Pine Avenue with it's quaint shops, wonderful... View all property information
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    Anna Maria, Anna Maria Island 34216
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Sunny Side-Up 267 Gladiolus Street Anna Maria, Fl. 34216 Trendy colorful, happy cottage located in popular Anna Maria City. This 2 bedroom 2 bath ground level home was completely renovated inside and out. All new furniture throughout with lots of fun decor and an island feel. A delight the... View all property information
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    Anna Maria, Anna Maria Island 34216
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Life is Good at the Beach, located on the north end of Anna Maria Island, is a fantastic place to start your vacation. This three-bedroom, two-bath, vacation rental is just a five minute walk to the beautiful north end beaches near Bean Point and two blocks to the Rod & Reel Pier. The extra-large... View all property information
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    Anna Maria, Anna Maria Island 34216
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    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    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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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    Sundown North 300 N. Shore Dr. - Unit B Anna Maria, Fl. 34216 Sundown North- a unique water front property that has 4 bedrooms, 3 bathrooms and a private heated pool one block to Pine Ave. It sleeps up to 8 guests in beds and 10 total. Sundown North also has a separate living room upstairs... View all property information
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    Anna Maria, Anna Maria Island 34216
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Pets allowed
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    About this property
    Located in the heart of Anna Maria, a gorgeous and spacious Mediterranean style 4 Bedroom/3 Bath Home with a Heated Pool in a very private and peaceful setting. Only steps to Pine Avenue shopping and Trolley Stop, 2 blocks to the Beach, and walking distance to the Pier. The open floor plan features... View all property information
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    Anna Maria, Anna Maria Island 34216