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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

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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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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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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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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503 South Bay Blvd - 503sb - Condo Rental

503 South Bay Blvd - 503sb

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,800
Month

Welcome to Belleair Beach, one of the last strictly residential beach communities in all of Pinellas County! You'll find a relaxed and peaceful atmosphere in a… More →

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111 Willow - Condo Rental

111 Willow

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,500
Week

Tour: http://www.pfretour.com/2688 Spend your vacation just steps from our beautiful beaches and crystal-clear waters! Casa Blanca is in the heart of the … More →

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Harbour Villa Club Unit 203 - Condo Rental

Harbour Villa Club Unit 203

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,350
Week

On beautiful Sarasota Bay in a lush tropical setting, Harbour Bay Club is on Dream Island, only a short walk to the famous beaches of Longboat Key. Comfortably… More →

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Beach Castle Unit-16 - Bc16 - Condo Rental

Beach Castle Unit-16 - Bc16

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$861
Week

This newly renovated spacious 2nd floor 2 Bedroom 2 Bath condo has a vaulted, windowed ceiling for extra light. Beautiful designer tile throughout Lovely garden… More →

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Beach Castle Unit-14 - Bc14 - Condo Rental

Beach Castle Unit-14 - Bc14

Condo Rentals in Anna Maria Island, Florida

1
Beds

1
Baths

$693
Week

Lovely 1 bedroom 1 bath rental unit on the second floor sleeps 2 people. Freshly painted throughout, nicely furnished and skylights in the ceiling for lots of … More →

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Perico Island Flamingo Cay - Condo Rental

Perico Island Flamingo Cay

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,200
Week

Located in Flamingo Cay in Perico Bay area just off of Anna Maria Island. This is a gorgeous 3 bedroom home with a very relaxing interior atmosphere. Carpet in … More →

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Beach Castle Unit-5 - Condo Rental

Beach Castle Unit-5

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,190
Week

This updated first floor 2 bedroom, 2 bath condominium has a partial view of the Gulf of Mexico from the screened in lanai, and is just steps away from the … More →

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Ami Beach Resort Rm 11 - Condo Rental

Ami Beach Resort Rm 11

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,450
Week

Two bedroom, pool side and garden view, nicely furnished. In the heart of Anna Maria Island, this resort has it all, King size bed, and Queen size bed in 2nd … More →

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Beach Castle Unit-9 - Condo Rental

Beach Castle Unit-9

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,050
Week

A view of the Gulf, but more economical than the other Gulffront condominium at the Beach Castle Resort, the owners have spared no expense in renovating this … More →

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Ami Beach Resort Room 5 - Condo Rental

Ami Beach Resort Room 5

Condo Rentals in Anna Maria Island, Florida

1
Beds

1
Baths

$900
Week

One bedroom, garden & partial beach view, nicely furnished on 2nd level. In the heart of Anna Maria Island, this resort has it all, King size bed, fully … More →

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Beach Castle Unit-26 - Bc26 - Condo Rental

Beach Castle Unit-26 - Bc26

Condo Rentals in Anna Maria Island, Florida

1
Beds

1
Baths

$798
Week

Enjoy one of the best views of Sarasota Bay in the entire complex from this one bedroom, one bath second floor unit. Completely redecorated with new tile … More →

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Beach Villa – 207 71st St - Condo Rental

Beach Villa – 207 71st St

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$443
Week

The perfect spot for the budget-conscious, beach-loving vacationer! This comfortable and clean 2 bedroom/2 bath elevated duplex is only 200 yards from the … More →

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Beach Castle Unit-6 - Condo Rental

Beach Castle Unit-6

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,190
Week

A view of the Gulf, but more economical than one of the other Gulf Front apartments at the Beach Castle, the owners have spared no expense in updating this … More →

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Triplex Unit B - Condo Rental

Triplex Unit B

Condo Rentals in Anna Maria Island, Florida

2
Beds

1
Baths

$900
Week

Nice Two Bedroom with Pool area and BBQ. This unit is in an excellent location. It has all the amenities needed either for a short stay or longer. This Unit is… More →

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Ami Beach Resort Room 10 - Condo Rental

Ami Beach Resort Room 10

Condo Rentals in Anna Maria Island, Florida

2
Beds

2
Baths

$1,200
Week

Two Bedroom, Pool side, partial gulf view, nicely furnished on the second level. In the heart of Anna Maria Island, this resort has it all, King size beds, … More →

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