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Anna Maria Island Cottage & Vacation Rentals

Florida South Gulf Coast, Florida, US

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About Anna Maria Island

Anna Maria Island is an excellent travel destination when looking to get away from it all and head out to Cottage Country. Anna Maria Island is full of nature to explore. When you visit Anna Maria Island be prepared to take advantage of all the excellent activities Anna Maria Island has to offer.

When planning your trip to Anna Maria Island note that there are many excellent private cottage rentals to choose from. Make sure you browse through the Anna Maria Island listings and pick the one that is right for you and your family.

United States → Florida → Florida South Gulf Coast → Anna Maria Island
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1 - 18 of 92 Holiday Rentals
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106 36th Street

Vacation Homes in Anna Maria Island, Florida - #187891
106 36th Street
From
$1,820 / week
Bedrooms
3
Bathrooms
2
Sleeps
5-6
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
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 thing or two ... More →
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Bayou Hideaway

Condos in Anna Maria Island, Florida - #187807
Bayou Hideaway
From
$550 / week
Bedrooms
2
Bathrooms
1
Sleeps
5-6
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
These charming condos are nestled right in the heart of the historic village of Anna Maria. Located at the northeast end of Pine Avenue, you'll be just across the street ... More →
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Anna Maria Island Club #18

Vacation Homes in Anna Maria Island, Florida - #187881
Anna Maria Island Club #18
From
$1,300 / week
Bedrooms
2
Bathrooms
2
Sleeps
5-6
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
Anna Maria Island Club offers some of the finest vacation condos in the area. And the view from Unit 18 is especially breathtaking. The Gulf of Mexico stretches out into ... More →
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5613 Gulf Drive

Vacation Homes in Anna Maria Island, Florida - #187886
5613 Gulf Drive
From
$636 / week
Bedrooms
2
Bathrooms
2
Sleeps
5-6
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
Frank Lloyd Wright is known from bringing the world what he considered “organic architecture”. He believed in buildings that focused on balance between humanity and ... More →
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Beach Castle Unit-6

Condos in Anna Maria Island, Florida - #187796
Beach Castle Unit-6
From
$1,190 / week
Bedrooms
2
Bathrooms
2
Sleeps
5-6
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
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 condo. ... More →
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Genesis II – 6385 Gulf Of Mexico

Vacation Homes in Anna Maria Island, Florida - #187797
Genesis II – 6385 Gulf Of Mexico
From
$1,000 / week
Bedrooms
2
Bathrooms
2
Sleeps
5-6
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
Picturing lazy days on the beach? Get your bathing suit and flip flops, and settle in for the most relaxing vacation ever! This charming two bedroom/two bath cottage is ... More →
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116 Maple Ave

Vacation Homes in Anna Maria Island, Florida - #187817
116 Maple Ave
From
$1,400 / week
Bedrooms
4
Bathrooms
2.5
Sleeps
7-8
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
Located on one of the prettiest streets in the village of Anna Maria, this lovely 4 bedroom, 2 and a half bath home is just 7 houses away from the beach. The quiet, tree-... More →
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1000 Gulf Drive

Condos in Anna Maria Island, Florida - #187873
1000 Gulf Drive
From
$700 / week
Bedrooms
1
Bathrooms
1
Sleeps
3-4
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
Welcome to the Beach House Resort, located just blocks from downtown Bradenton Beach, Florida on beautiful Anna Maria Island! This Gulf front vacation rental condo is ... More →
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Beach Castle Unit-9

Condos in Anna Maria Island, Florida - #187793
Beach Castle Unit-9
From
$1,050 / week
Bedrooms
2
Bathrooms
2
Sleeps
7-8
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
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 condo. All ... More →
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Beach Castle Unit-26 - BC26

Condos in Anna Maria Island, Florida - #187792
Beach Castle Unit-26 - BC26
From
$798 / week
Bedrooms
1
Bathrooms
1
Sleeps
3-4
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
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 throughout, new ... More →
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509 Spring Paradise

Vacation Homes in Anna Maria Island, Florida - #188384
509 Spring Paradise
From
$1,000 / week
Bedrooms
2
Bathrooms
2
Sleeps
3-4
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
Beautifully remodeled and professionally decorated 2 bedroom, 2 bath elevated home in the heart of Anna Maria City. Close to Tampa Bay and the City Pier, this home sits ... More →
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213 70th Street

Vacation Homes in Anna Maria Island, Florida - #187888
213 70th Street
From
$1,175 / week
Bedrooms
3
Bathrooms
2
Sleeps
7-8
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
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 vacation and a ... More →
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422 Spring Chilifish

Vacation Homes in Anna Maria Island, Florida - #188375
422 Spring Chilifish
From
$1,600 / week
Bedrooms
3
Bathrooms
2
Sleeps
5-6
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
You can’t imagine anyone not falling in love with the exquisite Chillifish, a peaceful gem, decorated with the utmost attention to details and surrounded by a garden ... More →
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Bermuda Bay Unit 14

Condos in Anna Maria Island, Florida - #188425
Bermuda Bay Unit 14
From
$900 / week
Bedrooms
3
Bathrooms
2.5
Sleeps
7-8
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
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 Refrigerator, ... More →
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7302 Palm Drive

Vacation Homes in Anna Maria Island, Florida - #187882
7302 Palm Drive
From
$500 / week
Bedrooms
2
Bathrooms
1
Sleeps
7-8
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
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 palm trees... More →
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779 Jacaranda Road

Vacation Homes in Anna Maria Island, Florida - #187885
779 Jacaranda Road
From
$1,023 / week
Bedrooms
3
Bathrooms
2
Sleeps
7-8
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
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 plus den ... More →
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208B 72nd Anna Rose

Vacation Homes in Anna Maria Island, Florida - #188388
208B 72nd Anna Rose
From
$1,700 / week
Bedrooms
4
Bathrooms
2.5
Sleeps
7-8
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
Unwind in the tropical paradise and Old Florida Charm of this single family pool home on Anna Maria Island at Anna Rose. This 4 bedroom 2.5 bath pool home is located in ... More →
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West Bay Pt Moorings Unit 64

Condos in Anna Maria Island, Florida - #187794
West Bay Pt Moorings Unit 64
From
$475 / week
Bedrooms
2
Bathrooms
2
Sleeps
3-4
Region
Florida South Gulf Coast
City
Anna Maria Island, Florida
Enjoy one of the most breathtaking views on the island from this lovely two bedroom/two bath upstairs unit at West Bay Point Moorings. Not only are the views spectacular... More →
1 - 18 of 92 Holiday Rentals

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