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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

What to Do Here

What to do 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 →


Waterside

Condo Rentals in Anna Maria Island, Florida

5
Beds

4+
Baths

$2,500
Week

Luxurious Island accommodations await! This elegant waterfront home is sure to please even the most discriminating guest, with breathtaking views across the Bay… More →


At Last - 308 Spring Ave

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,500
Week

Tour: http://www.pfretour.com/2079 At Last….. Imagine yourselves on a beautiful island with warm sunshine, surrounded by palm trees, white sand beaches and a … More →


Island Escape – 214 Lakeview Dr

Condo Rentals in Anna Maria Island, Florida

3
Beds

3
Baths

$2,310
Week

Escape to this lovely 3 bedroom/3 bath waterfront home, nestled on the shores of Lake LaVista in the village of Anna Maria. Now a meandering, mangrove-lined … More →


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 →


779 Jacaranda Road - Vacation Home

779 Jacaranda Road

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$1,023
Week

What a special place! Remember days gone by in this Key West style holiday rental with sparkling pool in a tropical paradise setting. Three spacious bedrooms … More →


Waters Edge #109 North - Vacation Home

Waters Edge #109 North

Vacation Homes in Anna Maria Island, Florida

2
Beds

2
Baths

$1,550
Week

Enjoy a magical sunset in this updated Gulf of Mexico DIRECT beachfront Condo... Perfect family condo for a holiday rental with a large heated pool and nestled … More →


619 Rose Street - Condo Rental

619 Rose Street

Condo Rentals in Anna Maria Island, Florida

3
Beds

3.5
Baths

$2,300
Week

Absolutely stunning in every way! This ultimate luxury beach vacation rental home is for relaxing with family and friends at the highly coveted north end of … More →


3008 Avenue E - Vacation Home

3008 Avenue E

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$118
Week

Here in Florida, we’re called the “Sunshine State” for the same reason South Dakota is the “Mount Rushmore State”. Because we know why people come to … More →


Bermuda Bay Club #26 - Vacation Home

Bermuda Bay Club #26

Vacation Homes in Anna Maria Island, Florida

3
Beds

2.5
Baths

$950
Week

Welcome to the Bermuda Bay Club located just blocks from downtown Bradenton Beach, Florida on beautiful Anna Maria Island! Jump the free Trolley, ride to Holmes… More →


213 70th Street - Vacation Home

213 70th Street

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$1,175
Week

A good vacation is thick like honey. It slows down time to a drag; everything feels sweet and golden and indulgent. This is especially true of a Florida … More →


106 36th Street - Vacation Home

106 36th Street

Vacation Homes in Anna Maria Island, Florida

3
Beds

2
Baths

$1,820
Week

On Anna Maria Island, there are no high rise hotels. Life is better on the beach because it’s simpler. But don’t let the flip flops fool you; we know a … More →


Runaway Bay 279 - Vacation Home

Runaway Bay 279

Vacation Homes in Anna Maria Island, Florida

1
Beds

1
Baths

$725
Week

New features include wireles internet service, extended cable, digital phone with free nationwide long distance. If outside entertainment is what you desire … More →


748 North Shore - Condo Rental

748 North Shore

Condo Rentals in Anna Maria Island, Florida

3
Beds

2
Baths

$1,700
Week

Florida is pretty notorious for sweet things. Oranges, key lime pie, and drippy ice cream of course, but we can’t forget 748 N Shore. This holiday cottage … More →


6407b Gulf Drive - Vacation Home

6407b Gulf Drive

Vacation Homes in Anna Maria Island, Florida

2
Beds

2
Baths

$1,000
Week

Recently remodeled island duplex just steps to the pristine Gulf of Mexico beaches of Holmes Beach. This vacation rental has been lovingly remodeled, and … More →


Bermuda Bay Unit 22 - Condo Rental

Bermuda Bay Unit 22

Condo Rentals in Anna Maria Island, Florida

3
Beds

2.5
Baths

$900
Week

Miles of White Sandy Beaches Gorgeous unit, three private decks to relax on. Two car garage for secure and covered parking. Fully equipped Kitchen with … More →


Triplex Unit A - Condo Rental

Triplex Unit A

Condo Rentals in Anna Maria Island, Florida

2
Beds

1
Baths

$1,050
Week

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


3000 Gulf Drive 8 - Condo Rental

3000 Gulf Drive 8

Condo Rentals in Anna Maria Island, Florida

1
Beds

1
Baths

$599
Week

Second floor condo with peeks from the front porch of the Gulf of Mexico. A new kitchen was just installed in this well cared for condo. This island vacation … More →


7302 Palm Drive - Vacation Home

7302 Palm Drive

Vacation Homes in Anna Maria Island, Florida

2
Beds

1
Baths

$500
Week

Peaceful Palms is more than a vacation rental, it is a slice of island life that you can call you own. Ease into your home away from home by pulling up swaying … More →


Sandy Pointe 208 - Vacation Home

Sandy Pointe 208

Vacation Homes in Anna Maria Island, Florida

2
Beds

2
Baths

$693
Week

Sandy Pointe II unit 208, at 3607 East Bay Drive in Holmes Beach on Anna Maria Island, FL is a bright and airy, two bedrooms, and two bath holiday condo in a … More →


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