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House Rentals in Anna Maria Island, FL

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    695 Vacation Rentals in Anna Maria Island
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    $3,001
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    Overview Reviews (8)
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    $490
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    1 / 27
    5 of 5 stars (2) Excellent
    Overview Reviews (2)
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    $772
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    5 of 5 stars (1) Excellent
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    $1,715
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    1 / 17
    Anna Maria
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    Overview Reviews (12)
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    • Stereo System
    • Air Conditioning
    • Internet Access
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    • Dryer
    • Grill
    • Waterfront
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    About this property
    Celebrate the day with the brilliant sunshine, glorious sunsets and star-studded skies! This luxury three-bedroom two-bath Gulf-front beach home is located in a quiet, secluded area of Anna Maria Island at 103-45th Street in Holmes Beach. The white sandy beach stretches for miles along the length... View all property information
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    $1,158
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    4.5 of 5 stars (4) Very good
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (4)
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    • ?
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    About this property
    Palm Cay 5 located at 3000 Gulf Drive in Holmes Beach is a very spacious three bedroom, two bath town home located west of Gulf Drive for easy beach access. The complex features a very large heated pool and onsite laundry room. The complex is about one half block to the beach and is very convenient... View all property information
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    $315
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    Overview Reviews (6)
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    • Dryer
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    • DVD Player
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    • Wi-Fi
    • Garage
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Just steps from the white sand beaches of Anna Maria Island, this four-bedroom, three bath, family-friendly vacation rental is located on the north end of the island in the city of Anna Maria. With a new heated pool, a large, covered and furnished balcony and patio, a gas grill, plus an organic... View all property information
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    1 / 21
    Holmes Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Away to Play 117 White Avenue Holmes Beach Fl. 34217 This grand Victorian style Island home is luxury at its best! A newly constructed 4 bedroom, 2.5 bath elevated home with a private heated pool is surrounded by tropical landscaping. You will find Away to Play is a very short walk to the Gulf... View all property information
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    $608
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    Overview Reviews (7)
    Amenities & Details
    • Fireplace
    • Deck
    • Satellite TV
    • Washer
    • Waterfront
    • Air Conditioning
    • Sauna
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
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    About this property
    Located on the north end of Anna Maria Island in the city of Anna Maria, this family-friendly vacation rental was built for rest and relaxation. Beginning with the lush landscaping that meets you at the front door, all the way through to the putting green, kayak launch and boat dock, this house has... View all property information
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    $175
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    1 / 22
    4 of 5 stars (1) Very good
    Overview Reviews (1)
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Villa Florence 4104 6th Ave. Holmes Beach, FL. 34217 Villa Florence is a magnificent 3 bedroom/ 3 bathroom villa that exudes Mediterranean style. Gated at the front, it has pristine landscaped grounds full of palm trees and tropical plants. Walking through the entrance of this home, you are... View all property information
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    $191
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    1 / 15
    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (1)
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Aloha Home 206 55th Street Holmes Beach, Fl. 34217 This is a gorgeous 3 bedroom, 2 bath home with a heated pool. Spectacular and unsurpassed tropical landscaping surrounds the entire home - especially the private pool area. The outdoor paver patio is partially covered for a break from the... View all property information
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    $245
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    1 / 12
    5 of 5 stars (1) Excellent
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Overview Reviews (1)
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Refrigerator
    • Internet Access
    • Satellite TV
    • Cooker
    • Washer
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
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    About this property
    h. This beachfront property is absolutely charming.!! 2 bedrooms 2 full bathrooms; sleeps 4-6;walk out to the powder white sand beach. This unit offers a recently remodeled built 2 bedroom, 2 bath first floor walk out villa. Enjoy the open deck with stairs right to the sandy beach. Off the living... View all property information
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    1 / 22
    3.5 of 5 stars (9) Average
    Overview Reviews (9)
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki... View all property information
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    $209
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    Overview Reviews (6)
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    • Private Outdoor...
    • Grill
    • Linens Provided
    • Satellite TV
    • Cooker
    • Refrigerator
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    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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    $379
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    1 / 23
    5 of 5 stars (2) Excellent
    Overview Reviews (2)
    Amenities & Details
    • Refrigerator
    • Air Conditioning
    • Dryer
    • Internet Access
    • Garage
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    $3,730
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    1 / 22
    4.5 of 5 stars (2) Very good
    Overview Reviews (2)
    Amenities & Details
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Views, views, views! You will love watching the waves and the sunset over the sandy Gulf beach—one hundred steps away—as well as the boats and the sunrise over the Bay. New and modern throughout, Sans Souci offers two complete units with three bedrooms, two baths each. The master bedroom has a king... View all property information
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    $256
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    1 / 17
    4 of 5 stars (1) Very good
    Anna Maria
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (1)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Sunchase Villa 302 Gulf Blvd Anna Maria, Fl. 34216 Sunchase Villa is a true Old Florida, ground level beach cottage nestled on the north end of Anna Maria Island only a short walk to restaurants and shopping. There are fantastic Gulf Views from this well-appointed 4 bedroom, 4.5 bath private... View all property information
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    $404
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    1 / 24
    Anna Maria
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Villa Del Sol 211 Chilson Avenue Anna Maria, FL 34217 This is an exquisite, newly remodeled 5 bedroom, 3 bath ground level home with available boat dock. Inside the home you will find quality furnishings with a Caribbean decor. The open floor plan provides the perfect space for spending... View all property information
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    $326
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    1 / 38
    5 of 5 stars (1) Excellent
    Overview Reviews (1)
    Amenities & Details
    • Deck
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Hot Tub
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful, Brand New, Waterfront, 3 bedroom/2 bath home with Heated Pool, Dock, and just over a block to the beach! Covered Patio by pool area and beautiful views of the canal from the Dock. Great location in a quiet neighborhood, a few steps to the Trolley Stop, and a short walk to the Public... View all property information
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    $136
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    1 / 20
    5 of 5 stars (3) Excellent
    Anna Maria
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Overview Reviews (3)
    Amenities & Details
    • Cooker
    • Satellite TV
    • Refrigerator
    • Washer
    • Boat Available
    • Dryer
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    $2,573
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    1 / 22
    5 of 5 stars (14) Excellent
    Overview Reviews (14)
    Amenities & Details
    • Waterfront
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
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    About this property
    The Bradenton Beach Club Unit D, located at 1700 Gulf Drive is a luxury gulf-front complex featuring an elevator, two heated pools, spa and bayside gazebo. This is a premier Bradenton Beach rental property! This spacious condo has panoramic beach views yet just across the street is a boardwalk... View all property information
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    Overview Reviews (4)
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    • Washer
    • Waterfront
    • Dryer
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Grill
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come and enjoy your own private Island Oasis! Located on the north end of Anna Maria Island in the city of Anna Maria, one block from the bay and a few blocks from the City Pier, this charming vacation rental will allow for some serious relaxation. This home-away-from-home offers two bedrooms and... View all property information
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    $256
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    1 / 19
    Anna Maria
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Casa Muratti 210 Palmetto Avenue Anna Maria Fl. 34216 This is an exceptional 4 bedroom 3.5 bath Mediterranean style home just a short walk to the Gulf of Mexico. With its modern decor and bright open floor plan this home is perfect for your vacation getaway! There is a private heated pool and a... View all property information
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    $209
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    Overview Reviews (1)
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    • Wi-Fi
    • Private Outdoor...
    • Garage
    • Grill
    • Satellite TV
    • DVD Player
    • Dryer
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
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    About this property
    This elevated vacation rental has been newly renovated to meet your high standards of vacation home living. With over 1400 square feet of living space, this home boasts three large bedrooms with a king master suite, a queen in the second bedroom, and a twin in the third. A queen sofa bed in the... View all property information
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    1 / 17
    5 of 5 stars (5) Excellent
    Overview Reviews (5)
    Amenities & Details
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Seacrest II Condo, Unit #4 at 3703 5th Avenue in Holmes Beach, is a very comfortably furnished and recently updated unit in a smaller complex, just a few short steps to the beach and located out of the way on a dead end street. Seacrest offers a heated pool, and every amenity to make your stay here... View all property information
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    $174
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    Overview Reviews (4)
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    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Water Views
    • Wi-Fi
    • Elevator/Lift access
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Grab your flip flops and get ready to head to the beach when staying in this Gulf Sands condo! With a private balcony overlooking the turquoise waters of the Gulf of Mexico, this vacation rental is a fantastic place to stay during your Anna Maria Island vacation. There is plenty of space for... View all property information
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    $323
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    Overview Reviews (4)
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    • Grill
    • Wi-Fi
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    • Washer
    • Private Outdoor...
    • Deck
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This beautifully furnished four-bedroom, 3.5-bath Anna Maria Island vacation rental is just over a block to the beach! With a large great room layout and balconies in front and rear of the house there is plenty of room for vacationing in this awesome home. On the main floor you will find the main... View all property information
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    1 / 15
    Anna Maria
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Windsong Cottage 119 Beach Avenue Anna Maria, Fl 34216 Windsong Cottage is a charming 2 bedroom 2 bath elevated home just five houses from the Gulf. It has an open floor plan with new, comfortable furnishings that make you feel *right at home*. The plantation shutters add to that 'Old... View all property information
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    $2,842
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    Overview Reviews (17)
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    The Harrison Home is a very spacious three bedroom, four bath pool home located at 6901 Gulf Drive in Holmes Beach, just 150' to a beautiful sandy beach. Located in the preferred northern end of Holmes Beach, this home features a private pool with fenced yard, poolside gazebo, extensive new... View all property information
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    $3,550
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    • Pet-friendly
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    • Child-friendly
    • ?
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    • Elder access
    • ?
    • ?
    About this property
    The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect!Each unit features a large covered... View all property information
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    $420
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    1 / 39
    5 of 5 stars (2) Excellent
    Overview Reviews (2)
    Amenities & Details
    • Dryer
    • Internet Access
    • Grill
    • Garage
    • Washer
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    $1,072
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    4.5 of 5 stars (9) Very good
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (9)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • ?
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    About this property
    The Dolphin Dance North side, located at 803 Gulf Drive South is an impressive, two bedroom one and one half bath duplex with panoramic views of the Gulf of Mexico.This spacious, town home unit will sleep six with a queen size bed, a full size bed and a sofa bed. Extras include washer, dryer, VCR,... View all property information
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    $1,930
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    1 / 21
    4 of 5 stars (4) Very good
    Overview Reviews (4)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • ?
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    About this property
    The Dolphin Dance, located at 803 and 805 Gulf Drive South is an impressive duplex with unobstructed, panoramic views of the Gulf of Mexico. Each side has two bedrooms and one and one half baths. Each sleeps six with a queen size bed, two double beds and a sofa bed. There is a shared washer and... View all property information
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    $288
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    Overview Reviews (7)
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    • Private Outdoor...
    • Wi-Fi
    • DVD Player
    • Dryer
    • Satellite TV
    • Patio
    • Garage
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This four-bedroom pet-friendly vacation rental with a heated pool is just a block to the white sand beaches of Anna Maria Island and the Gulf of Mexico. Located in Holmes Beach, Beautiful Villa by the Sea offers an open floor plan with plenty of space to accommodate 10. On the main floor you will... View all property information
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    $153
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    Overview Reviews (8)
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Anna Maria Beach Place #2, located at 201 35th Street in Holmes Beach is a charming beachside complex featuring six units surrounding a heated pool and tropical gardens. Immediately across a rarely traveled, dead end road are the white sandy beaches and the emerald green water of the Gulf of... View all property information
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    4 of 5 stars (1) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (1)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Beach Bliss 304 58th St. Unit A Holmes Beach, Fl. 34217 If you are looking for that perfect cozy island vacation getaway, than look no further! Centrally located to all that Anna Maria Island has to offer this 2 bedroom and 2 bathroom newly constructed private duplex has got it all! The tropical... View all property information
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    $613
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    1 / 10
    5 of 5 stars (2) Excellent
    Bradenton Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (2)
    Amenities & Details
    • Stereo System
    • Washer
    • Grill
    • Internet Access
    • Balcony
    • Refrigerator
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The Villas is a small, 5 unit complex with a pool located steps from downtown Bradenton Beach and the beautiful white sand beaches of Anna Maria Island. All the units are clean and tastefully decorated with new ceramic tile floors and appliances. The complex offers FOUR 1 bedroom, 1 bath units and... View all property information
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    $1,348
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Satellite TV
    • Refrigerator
    • Hot Tub
    • Dryer
    • Washer
    • Balcony
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    About this property
    2-bedroom/2-bath units directly on the Gulf of Mexico with its perfect snow-white beach. Large private terrace, views of the Gulf from both living/dining area and master bedroom. This is the perfect place to enjoy your vacation! Building has heated pool, Jacuzzi, covered parking, elevator and... View all property information
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    5 of 5 stars (4) Excellent
    Overview Reviews (4)
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    About this property
    Seaside Beach House #103 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a heated pool at beachside. 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. The beach... View all property information
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    About this property
    Anna Cabana Bungalow #2 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a perfect complex for... View all property information
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    4.5 of 5 stars (9) Very good
    Holmes Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Terrace Condominium #2, located at 3100 Gulf Drive in Holmes Beach is a beautifully and comfortably furnished, two bedroom, two bath town home condo with heated pool, private garage and three separate lanais. The pool area is beautifully landscaped with native plants and features a pergola and... View all property information
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    • Water Views
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    About this property
    The Island Bay House is a glorious four bedroom four bathroom bay front duplex located at 232 South Harbor Drive in Holmes Beach. This spacious duplex features an elevator, boat dock, heated indoor pool and spa. This property features spectacular panoramic views of the Intracoastal and Tampa Bay... View all property information
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    Holmes Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Seaside Gardens 460 63rd Street Holmes Beach, Fl 34217 This lovely canal front, ground level, attached bungalow offers fantastic views and amenities! Enjoy the shared deep water dock right off of your backyard, community tennis courts, private ping-pong table, board games and so much more! This... View all property information
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    4 of 5 stars (1) Very good
    Overview Reviews (1)
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    About this property
    Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private... View all property information
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    4.5 of 5 stars (20) Very good
    Bradenton Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    About this property
    Coquina Beach Club #101 is a beautiful two bedroom, two bath Gulf front condo with a heated pool. This spacious unit has an unobstructed view of the emerald water of the Gulf and you can walk the beach is for miles in either direction. The complex has a large heated pool and undercover parking.... View all property information
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    • Private Outdoor...
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    • Air Conditioning
    • Wi-Fi
    • Washer
    • Satellite TV
    • Dryer
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    • Pet-friendly
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    About this property
    Escape to Serenity sums it up for this quaint and cozy duplex (with no shared walls). You will feel as if you have landed on your own personal island with this gem of a property. This fantastic, two-bedroom, one-bathroom vacation rental will help you find some serenity. This home boasts an all-new... View all property information
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    • Child-friendly
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    About this property
    The Lake by the Beach at 6806 Palm Drive offers the best of both worlds! This beautiful two bedroom, two bath home is situated on a spring fed lake yet it's only three blocks to the beach. New renovations include a brand new family room addition with easy access to the beautiful pool!A unique and... View all property information
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    Overview
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    About this property
    Welcome to the Seahorse Beach House on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. The Seahorse Beach House side includes a private heated pool (not shared), hot/cold outdoor... View all property information
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