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Anna Maria Island Vacation Rentals

Anna Maria Island Vacation Rentals

Anna Maria Island Vacations

Vacation Rentals in Anna Maria Island, Florida

Located along Florida’s southern coast, at the southern tip of Tampa Bay and the Gulf of Mexico, Anna Maria Island and its vacation rentals lie scattered amongst sea oats and Australian pines, in “Old Florida” neighborhoods close to the water’s edge. 

The towns of Anna Maria, Brandenton Beach, and Holmes Beach line the eleven-kilometre long barrier island, famed for its sugar-white sand beaches and emerald waters. Several beaches provide areas for sunbathing, swimming, and beachcombing. Boating, sea kayaking, and windsurfing are possible in bays and on the Gulf. Fishing is another popular island-wide activity, from one’s boat or any one of the three piers. Several parks and trails provide opportunities to catch glimpses of manatees, sea turtles, and dolphins, as well as egrets, herons, and pelicans. 

Anna Maria Island is home to a variety of boutiques, galleries, restaurants, cafés, and ice cream shops, including Mama Lo’s and Dips Ice Cream & Candy Store. While most of the island can be explored on foot or by bike, there is also a free trolley service that takes you wherever you want to go. Anna Maria Island offers natural and outdoors attractions, as well as a variety of amenities and rental accommodation options, and is less than a thirty minutes’ drive northwest of Sarasota

What to Do

Activites in Anna Maria Island, Florida

On The Ocean
Beach
Hot Weather
Golf

Anna Maria Island Vacation Rentals & Vacation Homes

Villa Marisol - 797ns

Vacation Homes in Anna Maria Island, Florida

4
Beds

3.5
Baths

$3,500
Week

Villa Marisol, on the enviable north beach of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the … More →

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Grand Oak - 6358goak

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$475
Week

Grand Oak Circle is in a great location to take advantage of eveything that Sarasota, Bradenton and Anna Maria Island has to offer. Exploring other areas of FL … More →

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Lakeview Cottage – 216 Lakeview

Condo Rentals in Anna Maria Island, Florida

2
Beds

1.5
Baths

$595
Week

A wonderful mid-century modern cottage lovingly built by a master craftsman who turned down work from Frank Lloyd Wright himself! Most of the beautiful trees on… More →

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Lacasa Costiera - La Casa 12

Cottage Rentals in Anna Maria Island, Florida

3
Beds

2.5
Baths

$3,095
Week

You'll be hard-pressed to find something more luxurious than this beautiful three bedroom, two-and-a-half bath unit at the prestigious La Casa Costiera. These … More →

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The Shore 113

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$3,000
Month

The Shore is a Gulf-front complex located near the north end of the island, with exquisite views from everywhere on the property. If you treasure your time on … More →

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Ra43526-Down By The Sea - 43526 - Florida South Gulf Coast Vacation Home

Ra43526-Down By The Sea - 43526

Vacation Homes in Anna Maria Island, Florida

3
Beds

$1,190
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43538-Garden Cottage - 43538 - Florida South Gulf Coast Cottage Rental

Ra43538-Garden Cottage - 43538

Cottage Rentals in Anna Maria Island, Florida

2
Beds

$1,190
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43539-Grant's View - 43539 - Florida South Gulf Coast Cottage Rental

Ra43539-Grant's View - 43539

Cottage Rentals in Anna Maria Island, Florida

2
Beds

$1,120
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43457-Mangrove Cottage - 43457 - Florida South Gulf Coast Cottage Rental

Ra43457-Mangrove Cottage - 43457

Cottage Rentals in Anna Maria Island, Florida

2
Beds

$1,120
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43540-Sandy's Getaway - 43540 - Florida South Gulf Coast Vacation Home

Ra43540-Sandy's Getaway - 43540

Vacation Homes in Anna Maria Island, Florida

3
Beds

$1,120
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43483-Newly Remodeled Hardin Cottage - 43483 - Florida South Gulf Coast Vacation Home

Ra43483-Newly Remodeled Hardin Cottage - 43483

Vacation Homes in Anna Maria Island, Florida

3
Beds

$1,085
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43533-Peony House - 43533 - Florida South Gulf Coast Vacation Home

Ra43533-Peony House - 43533

Vacation Homes in Anna Maria Island, Florida

4
Beds

$1,155
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43557-Au Soleil - 43557 - Florida South Gulf Coast Vacation Home

Ra43557-Au Soleil - 43557

Vacation Homes in Anna Maria Island, Florida

4
Beds

$2,380
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43459-Rose Pleasant Home - 43459 - Florida South Gulf Coast Vacation Home

Ra43459-Rose Pleasant Home - 43459

Vacation Homes in Anna Maria Island, Florida

3
Beds

$945
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43543-North Shore Cottage - 43543 - Florida South Gulf Coast Cottage Rental

Ra43543-North Shore Cottage - 43543

Cottage Rentals in Anna Maria Island, Florida

3
Beds

$945
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43546-Star Fish Cottage - 43546 - Florida South Gulf Coast Vacation Home

Ra43546-Star Fish Cottage - 43546

Vacation Homes in Anna Maria Island, Florida

2
Beds

$1,050
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43493-Gorgeous Periwinkle Cottage - 43493 - Florida South Gulf Coast Cottage Rental

Ra43493-Gorgeous Periwinkle Cottage - 43493

Cottage Rentals in Anna Maria Island, Florida

3
Beds

$1,890
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43503-Periwinkle Home With Dock Access 208 - 43503 - Florida South Gulf Coast Vacation Home

Ra43503-Periwinkle Home With Dock Access 208 - 43503

Vacation Homes in Anna Maria Island, Florida

3
Beds

$1,505
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra43552-The Palms - 43552 - Florida South Gulf Coast Vacation Home

Ra43552-The Palms - 43552

Vacation Homes in Anna Maria Island, Florida

5
Beds

$1,680
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


Ra44276-My Sisters Beach House - 44276 - Florida South Gulf Coast Vacation Home

Ra44276-My Sisters Beach House - 44276

Vacation Homes in Anna Maria Island, Florida

5
Beds

$3,570
Week

Please note these Check-in Day Requirements for this property: Jun 01 - Jun 30 : Saturday check-in required, Saturday check-out required.; This property can … More →


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