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Anna Maria Island Vacation Rentals

VacationRentalDirect.com has found 17 Anna Maria Island Vacation Rentals that match your search criteria. Your results can be sorted by price, bedrooms, type of unit and whether the unit is pet friendly or not. All Anna Maria Island cottages, homes and vacation rentals are presented by their respective owners or managers.


Please click on the photos or links below to view the property details, then contact the owner directly (via the phone number or property inquiry button on each listing).

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Palm Tree Villas - Anna Maria Florida
Anna Maria Island, Florida

Just steps from the warm water of the Gulf of Mexico and the powder white Anna Maria Island beaches, enjoy the relaxing charm of southwest Florida accommodations
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Villa 2 1 No $650 to $1095

Anna Maria Island Beach Rentals
Anna Maria Island, Florida

150 miles of waterfront, 7 miles of white sand beach, free trolley service, private beach access, private shiltered parking, heated pool.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Condo 2 2 No $900 to $1150

Island Home with pool close to Beach
Anna Maria Island, Florida

Fantastic AND new....this elevated home is just a short block from lovely pristine sandy beaches.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
House 3 2 No $1350 to $1800

Adorable island home with pool
Anna Maria Island, Florida

So adorable! Island home with pool steps to the beach.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
House 2 1 No $950 to $1160

Direct Gulf front Luxury Condo with Heated Pool
Anna Maria Island, Florida

This luxurious brand new designer decorated gulf front condo is paradise IN paradise! Open Gulf water views and miles of white sandy beach at your footsteps on a bit of island paradise called Anna Maria Island.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Condo 3 2 No $2500 to $3300

Pelican Cove Condo with Gulf of Mexico Views
Anna Maria Island, Florida

Recently remodeled gulf to bay condo with endless Florida sunsets.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Condo 2 2 No $900 to $1250

A SeaShell Throw Away From Pristine Gulf Beaches
Anna Maria Island, Florida

Fantastic Island triplex.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Cottage 1 1 No $650 to $750

A writer's retreat in a lush tropical setting
Anna Maria Island, Florida

A private writer's retreat, this cozy two-bedroom just a short walk to the beach with a lush yard complete with a hammock between swaying palms. Beautifully decorated with a recently updated kitchen, this unique island h...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
House 2 1 No $835 to $958

Unique, beautiful home short walk to beach
Anna Maria Island, Florida

Our unique beautifully furnished island home offers a unique two-suite layout that converts into three bedrooms. Sleep under the mosquito net in the Africa room or work on high-speed internet in the Hemingway Office. Loc...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
House 3 2 No $835 to $985

3 Story "Nantucket-style" 4 bedroom Villa
Anna Maria Island, Florida

3 Story Villa set in a tropical setting. Just a short 2 minute walk to beautiful Gulf of Mexixo beach. Newly remodeled and professionally decorated 'Mary Engelbreit'. 4 Bedrooms/ 3 baths... 1 king bed, 3 queen beds, bu...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
House 4 3 No $1500 to $1750

Gulf-front Home on Most Beautiful Beach
Anna Maria Island, Florida

Traditional, beachfront, Florida bungalow has gulf views from its two spacious porches. Linger-Longer provides both the larger and smaller families with lots of privacy.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
House 4 3 No $0 to $0

A Serene Tropical Paradise
Anna Maria Island, Florida

Island Garden Villas is a lush tropical setting for your island adventure. Just across the street from the sugary white sands of the Gulf, the villas are a serene and relaxing retreat.
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Villa 2 2 Yes $700 to $1075

Beautiful Tropical Villa 100-ft to Pristine Beach
Anna Maria Island, Florida

Las Palmas is an immaculate 3 bedroom, 2 bath fully equipped ground floor unit only 2 homes from the beach. Located on a quiet dead-end street with no streets to cross to reach the pristine white sandy beaches of the Gu...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Villa 3 2 No $1185 to $1585

White Chairs is the Perfect Vacation Retreat
Anna Maria Island, Florida

Welcome to island vacationing at its best. WHITE CHAIRS is located a few steps away from the most beautiful beaches of all of Florida with seven miles of white sand and seashells. Everything you need for "fun in the sun"...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
House 2 2 Yes $785 to $885

Key west style accommodations 45 steps to the Gulf
Anna Maria Island, Florida

Cottage style accommodations with full kitchens and living rooms as well as pretty patios set among white arbors and tropical plantings. The Island's free trolley stops just across the street. Located just a short walk...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Cottage 1 1 Yes $650 to $895

Bird's Nest vacation apartments on Anna Maria isle
Anna Maria Island, Florida

The Bird's Nest vacation rentals beach apartments 2 bed rooms 2 baths on 1,200 square feet completely renovated, elegantly decorated and fully equipped offer a perfect beach vacation rental accommodation for enjoying a ...
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Apartment 2 2 No $870 to $1270

Seacrest - self catering rental condo with pool
Anna Maria Island, Florida

Seacrest - self catering rental condo with pool, near beach, sleeps 6
Type: Bedrooms Bathrooms Pet Friendly Weekly Rate
Condo 2 2 No $770 to $1085


Learn More About Anna Maria Island

Anna Maria Island has a lot to offer all visitors to the area. Below you will find writings from other Anna Maria Island vacation rental owners about the area they know best! It's a great way to learn first hand about the Anna Maria Island region and all that it has to offer!

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