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Anna Maria Island Vacation Rentals

Anna Maria Island Vacation Rentals

About Anna Maria Island

Travelling to 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

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What to do in Anna Maria Island, Florida

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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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Paradise Gulf Cottage - 6485gmd

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,500
Week

Enjoy a terrific holiday at Fairway Bay, one of south Longboat Key's most coveted addresses! It's easy to see why people love to stay at this beautiful, … 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

Cottage Rentals in Anna Maria Island, Florida

3
Beds

1
Baths

$3,192
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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Paradise Gulf Cottage 6485 Gmd - Vacation Home

Paradise Gulf Cottage 6485 Gmd

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$3,795
Week

This gracious home, with a pool and a private entrance to the beach, offers a lovely location on Longboat Key for all that the area has to offer. There is a … More →

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My Sisters Beach House - 44276 - Vacation Home

My Sisters Beach House - 44276

Vacation Homes in Anna Maria Island, Florida

5
Beds

4+
Baths

$3,455
Week

This property can only accept 7 nights stays with a check-in on Saturday Welcome to "My Sister's Beach House" on beautiful Anna Maria Island, Florida. This … More →


Casa Calienta - 43564 - Vacation Home

Casa Calienta - 43564

Vacation Homes in Anna Maria Island, Florida

2
Beds

2
Baths

$3,220
Week

This property can only accept 28 nights stays with a check-in on saturday. Non holiday weeks and no other discounts would apply Welcome to this new ground … More →


Seadreams - 43537 - Vacation Home

Seadreams - 43537

Vacation Homes in Anna Maria Island, Florida

4
Beds

3
Baths

$2,495
Week

This property can only accept 7 nights stays with a check-in on saturday. Enjoy fantastic sunsets and views of the aqua blue waters of the Gulf of Mexico from … More →


Au Soleil - 43557 - Vacation Home

Au Soleil - 43557

Vacation Homes in Anna Maria Island, Florida

4
Beds

3
Baths

$2,240
Week

This property can only accept 7 nights stays with a check-in on saturday. Welcome to Au Soleil just a short stroll to the sugar white sand beaches of beautiful… More →


Rest A Shore - 43562 - Vacation Home

Rest A Shore - 43562

Vacation Homes in Anna Maria Island, Florida

4
Beds

4+
Baths

$2,095
Week

This property can only accept 7 nights stays with a check-in on saturday. Sitting on the Tampa Bay! Tropical flowering bushes and swaying palm trees surround … More →


Dolphin Watch - 43426 - Vacation Home

Dolphin Watch - 43426

Vacation Homes in Anna Maria Island, Florida

2
Beds

1
Baths

$1,835
Week

This property can only accept 7 nights stays with a check-in on saturday. Sundrenched and colorful, this is a property as beautiful inside as the landscape … More →


Sundance - 43449 - Vacation Home

Sundance - 43449

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$1,820
Week

This property can only accept 7 nights stays with a check-in on Saturday Newly remodeled Island holiday home with peeks at the Gulf of Mexico and colorful … More →


Gorgeous Periwinkle Cottage - 43493 - Vacation Home

Gorgeous Periwinkle Cottage - 43493

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$1,815
Week

This property can only accept 7 nights stays with a check-in on saturday. Gorgeous completely renovated three bedroom, two bath large beach vacation rental … More →


All Decked Out - 43586 - Vacation Home

All Decked Out - 43586

Vacation Homes in Anna Maria Island, Florida

5
Beds

2
Baths

$1,770
Week

This property can only accept 7 nights stays with a check-in on saturday. Right across from the bayside beach and a short stroll to Pine Ave shopping and … More →


Bay-Front Shoreline Terrace - 43377 - Vacation Home

Bay-Front Shoreline Terrace - 43377

Vacation Homes in Anna Maria Island, Florida

3
Beds

3
Baths

$1,730
Week

This property can only accept 7 nights stays with a check-in on saturday. Direct bay front ground level home at the North End of Anna Maria Island. Enjoy … More →


Sweet Retreat Cottage - 43554 - Vacation Home

Sweet Retreat Cottage - 43554

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$1,730
Week

This property can only accept 7 nights stays with a check-in on saturday. Right across from the beach! This new ground level home awaits you and your family … More →


Pina Colada - 43577 - Vacation Home

Pina Colada - 43577

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$1,725
Week

This property can only accept 7 nights stays with a check-in on saturday. Pina Colada located just two blocks from Bean Point on beautiful Anna Maria Island, … More →


Unique White Home - 43438 - Vacation Home

Unique White Home - 43438

Vacation Homes in Anna Maria Island, Florida

4
Beds

2
Baths

$1,690
Week

This property can only accept 7 nights stays with a check-in on saturday. Ground level unique vacation rental home. This four bedroom two bath vacation home is… More →


Heavenly Sunset – 809 North Shore - Condo Rental

Heavenly Sunset – 809 North Shore

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,650
Week

Heavenly Sunsets are exactly what you'll experience at this lovely Bean Point home nestled among the sea oats at the north end of the island. Lush tropical … More →

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