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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

Bird's Nest Vacation Apartments On Anna Maria Island - Florida South Gulf Coast Vacation Home

Bird's Nest Vacation Apartments On Anna Maria Island

Vacation Homes in Anna Maria Island, Florida

2
Beds

2
Baths

$297
Night

Bird's Nest accommodations is a vacation rental complex of 4 town houses in Anna Maria island, Bradenton Beach, FL, south of Tampa/St. Petersburg and north-… More →

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Anna Maria's Finest ~ Ra61780 - Florida South Gulf Coast Vacation Home

Anna Maria's Finest ~ Ra61780

Vacation Homes in Anna Maria Island, Florida

3
Beds

3
Baths

$3,715
Week

When you stay at vacation rental home Anna Marias Finest youll experience the luxurious side of Anna Maria Island paradise. Equipped with everything 8 … More →

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Casa Campoamor ~ Ra43545 - Florida South Gulf Coast Vacation Home

Casa Campoamor ~ Ra43545

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$2,136
Week

Adorable three bedroom and two bath beach cottage rental so close to the beach you can smell the salt air. The sugar sand beach is only steps away at the end of… More →

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Gorgeous Periwinkle Cottage ~ Ra43493 - Florida South Gulf Coast Vacation Home

Gorgeous Periwinkle Cottage ~ Ra43493

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$2,680
Week

Periwinkles are small, sunshine loving flowers with a color so distinct they name crayons after it. On a street baring their name in Anna Maria Island, youll … More →

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Grande Haven ~ Ra48101 - Florida South Gulf Coast Vacation Home

Grande Haven ~ Ra48101

Vacation Homes in Anna Maria Island, Florida

6
Beds

3
Baths

Call
Week

Grande Haven is a spectacular example of high architecture, fine design and custom finishing at its best. This home was designed by the award winning Gene Leedy… More →

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Harmony House ~ Ra43387 - Florida South Gulf Coast Vacation Home

Harmony House ~ Ra43387

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$2,891
Week

Harmony House is such a special place! Remember days gone by in this Key West style holiday rental with a c"ocktail-style" sparkling pool in a tropical … More →

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Old Florida Charm ~ Ra43572 - Florida South Gulf Coast Vacation Home

Old Florida Charm ~ Ra43572

Vacation Homes in Anna Maria Island, Florida

2
Beds

2
Baths

Call
Week

Welcome to the "Old Florida" charm of this well cared for ground level cottage located at 215 Fir Ave and just a few homes from the best beaches in Florida. … More →

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Paradise Pointe ~ Ra48099 - Florida South Gulf Coast Vacation Home

Paradise Pointe ~ Ra48099

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$3,668
Week

Paradise Pointe, located in the quiet north end of beautiful Anna Maria awaits the vacationer in you. This picture perfect ground level three bedroom two … More →

HomeAway Partnership

Pina Colada ~ Ra43577 - Florida South Gulf Coast Vacation Home

Pina Colada ~ Ra43577

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

Call
Week

Welcome to 801 Jacaranda Road located at the north end of beautiful Anna Maria Island, less than 2 blocks from Bean Point Beach and the best sunset you will … More →

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

Putnam's Paradise ~ Ra43597

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

Call
Week

Welcome to 206 LakeView Drive located on the northern end of beautiful Anna Maria Island! This private and lovely vacation rental features all that you will … More →

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

Sandy's Getaway ~ Ra43540

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

Call
Week

Sandys Getaway, offers spacious and peaceful place to escape to right in the heart of Anna Maria City. Up to nine guests can spend a week, month, or long … More →

HomeAway Partnership

Sea's The Day ~ Ra43466 - Florida South Gulf Coast Vacation Home

Sea's The Day ~ Ra43466

Vacation Homes in Anna Maria Island, Florida

2
Beds

2
Baths

Call
Week

The various shades of blue throughout Sea's the Day make this a water lover's dream vacation cottage. Sitting about 200 steps to the beach access, it's like … More →

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Sugar Plum Hideaway East ~ Ra55239 - Florida South Gulf Coast Vacation Home

Sugar Plum Hideaway East ~ Ra55239

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$3,339
Week

Youll be pleased when you reserve Anna Maria Island vacation rental Sugar Plum Hide Away East an adorable ground level duplex located in the beautiful city … More →

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Sundance With So Well Stocked Kitchen ~ Ra43449 - Florida South Gulf Coast Vacation Home

Sundance With So Well Stocked Kitchen ~ Ra43449

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$2,939
Week

Theres a certain Florida way of life. Its about knowing you need to enjoy every day and slow down so you dont miss the sunset. With premium linens in three … More →

HomeAway Partnership

Willow Cottage ~ Ra43395 - Florida South Gulf Coast Vacation Home

Willow Cottage ~ Ra43395

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$2,774
Week

Willow Cottage is a lovely ground level bungalow in Anna Maria just waiting to give you that tropical vacation you dream of and deserve! This private rental … More →

HomeAway Partnership

Absolute Anna Maria - Anna Maria Island, Florida - Florida South Gulf Coast Condo Rental

Absolute Anna Maria - Anna Maria Island, Florida

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,500
Week

This luxurious Anna Maria Island vacation rentals beach condo is an immaculate 2 bedroom, 2 bathroom, first floor condo surrounded by four tropical bodies of … More →

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