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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

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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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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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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Ra43597-Putnam's Paradise - 43597 - Florida South Gulf Coast Vacation Home

Ra43597-Putnam's Paradise - 43597

Vacation Homes in Anna Maria Island, Florida

3
Beds

$1,400
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 →


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 →


Ra43577-Pina Colada - 43577 - Florida South Gulf Coast Vacation Home

Ra43577-Pina Colada - 43577

Vacation Homes in Anna Maria Island, Florida

3
Beds

$1,785
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 →


Ra43395-Willow Cottage - 43395 - Florida South Gulf Coast Cottage Rental

Ra43395-Willow Cottage - 43395

Cottage Rentals in Anna Maria Island, Florida

3
Beds

$1,610
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 →


Ra43596-Holly Jewel - 43596 - Florida South Gulf Coast Vacation Home

Ra43596-Holly Jewel - 43596

Vacation Homes in Anna Maria Island, Florida

3
Beds

$1,435
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 →


Ra43486-Bikini Bottom - 43486 - Florida South Gulf Coast Vacation Home

Ra43486-Bikini Bottom - 43486

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 →


Ra43542-Holly Hideaway - 43542 - Florida South Gulf Coast Vacation Home

Ra43542-Holly Hideaway - 43542

Vacation Homes in Anna Maria Island, Florida

2
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 →


Ra43545-Casa Campoamor - 43545 - Florida South Gulf Coast Vacation Home

Ra43545-Casa Campoamor - 43545

Vacation Homes in Anna Maria Island, Florida

3
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 →


Ra43377-Bay-Front Shoreline Terrace - 43377 - Florida South Gulf Coast Cottage Rental

Ra43377-Bay-Front Shoreline Terrace - 43377

Cottage Rentals in Anna Maria Island, Florida

3
Beds

$2,100
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 →


Ra43564-Casa Calienta - 43564 - Florida South Gulf Coast Vacation Home

Ra43564-Casa Calienta - 43564

Vacation Homes in Anna Maria Island, Florida

2
Beds

$2,975
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 →


Ra43426-Dolphin Watch - 43426 - Florida South Gulf Coast Vacation Home

Ra43426-Dolphin Watch - 43426

Vacation Homes in Anna Maria Island, Florida

2
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 →


Ra43591-La Vie En Rose - 43591 - Florida South Gulf Coast Vacation Home

Ra43591-La Vie En Rose - 43591

Vacation Homes in Anna Maria Island, Florida

3
Beds

$1,470
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 →


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 →


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