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Anna Maria Vacation Rentals

1 - 42 of 297 rentals
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Bay Breeze - Anna Maria, FL Vacation Rental

Bay Breeze

Anna Maria, FL
4 Bed 3 Bath Sleeps 8
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All Decked Out - Anna Maria, FL Vacation Rental

All Decked Out

Anna Maria, FL
5 Bed 3 Bath Sleeps 12
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Living the Dream - Anna Maria, FL Vacation Rental

Living the Dream

Anna Maria, FL
4 Bed 3 Bath Sleeps 8
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Sea Song - Anna Maria, FL Vacation Rental

Sea Song

Anna Maria, FL
2 Bed 1 Bath Sleeps 6
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Au Soleil - Anna Maria, FL Vacation Rental

Au Soleil

Anna Maria, FL
5 Bed 3 Bath Sleeps 10
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211 Elm A  - Anna Maria, FL Vacation Rental

211 Elm A

Anna Maria, FL
2 Bed 1 Bath Sleeps 6
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Sundance Cottage - Anna Maria, FL Vacation Rental

Sundance Cottage

Anna Maria, FL
3 Bed 2 Bath Sleeps 6
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Holly Hideaway - Anna Maria, FL Vacation Rental

Holly Hideaway

Anna Maria, FL
2 Bed 2 Bath Sleeps 4
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Emma's Cottage - Anna Maria, FL Vacation Rental

Emma's Cottage

Anna Maria, FL
3 Bed 2 Bath Sleeps 6
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3 Mermaids - Anna Maria, FL Vacation Rental

3 Mermaids

Anna Maria, FL
4 Bed 2.5 Bath Sleeps 8
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The Seashell Cottage - Anna Maria, FL Vacation Rental

The Seashell Cottage

Anna Maria, FL
2 Bed 2 Bath Sleeps 6
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Anna Maria's Finest - Anna Maria, FL Vacation Rental

Anna Maria's Finest

Anna Maria, FL
3 Bed 3 Bath Sleeps 8
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Dolphin Watch - Anna Maria, FL Vacation Rental

Dolphin Watch

Anna Maria, FL
2 Bed 1 Bath Sleeps 6
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Casa Bonita - Anna Maria, FL Vacation Rental

Casa Bonita

Anna Maria, FL
4 Bed 4 Bath Sleeps 8
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Shoreline Terrace - Anna Maria, FL Vacation Rental

Shoreline Terrace

Anna Maria, FL
4 Bed 2.5 Bath Sleeps 8
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Paradise Pointe - Anna Maria, FL Vacation Rental

Paradise Pointe

Anna Maria, FL
3 Bed 2 Bath Sleeps 8
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Blue Heron Beach House - Anna Maria, FL Vacation Rental

Blue Heron Beach House

Anna Maria, FL
4 Bed 2 Bath Sleeps 8
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Honeywood House - Anna Maria, FL Vacation Rental

Honeywood House

Anna Maria, FL
3 Bed 4 Bath Sleeps 8
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Dream Maker - Anna Maria, FL Vacation Rental

Dream Maker

Anna Maria, FL
3 Bed 3.5 Bath Sleeps 6
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Coconut Tree - Anna Maria, FL Vacation Rental

Coconut Tree

Anna Maria, FL
3 Bed 2.5 Bath Sleeps 8
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Blue Waters - Anna Maria, FL Vacation Rental

Blue Waters

Anna Maria, FL
4 Bed 4 Bath Sleeps 8
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Maple Cottage - Anna Maria, FL Vacation Rental

Maple Cottage

Anna Maria, FL
3 Bed 2 Bath Sleeps 8
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414 B Magnolia - Anna Maria, FL Vacation Rental

414 B Magnolia

Anna Maria, FL
2 Bed 1 Bath Sleeps 6
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Starfish Cottage - Anna Maria, FL Vacation Rental

Starfish Cottage

Anna Maria, FL
2 Bed 2 Bath Sleeps 6
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Sangria Sunrise - Anna Maria, FL Vacation Rental

Sangria Sunrise

Anna Maria, FL
3 Bed 3 Bath Sleeps 7
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Sea 'Esta - Anna Maria, FL Vacation Rental

Sea 'Esta

Anna Maria, FL
2 Bed 2 Bath Sleeps 5
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Harmony House - Anna Maria, FL Vacation Rental

Harmony House

Anna Maria, FL
3 Bed 2 Bath Sleeps 8
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Grant's View - Anna Maria, FL Vacation Rental

Grant's View

Anna Maria, FL
2 Bed 2 Bath Sleeps 6
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Pineapple Cottage - Anna Maria, FL Vacation Rental

Pineapple Cottage

Anna Maria, FL
4 Bed 3 Bath Sleeps 8
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Grande Haven - Anna Maria, FL Vacation Rental

Grande Haven

Anna Maria, FL
6 Bed 3 Bath Sleeps 16
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Sugar Plum Hideaway East - Anna Maria, FL Vacation Rental
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Cayman Bay - Anna Maria, FL Vacation Rental

Cayman Bay

Anna Maria, FL
4 Bed 4 Bath Sleeps 8
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Waterfront Retreat - Anna Maria, FL Vacation Rental

Waterfront Retreat

Anna Maria, FL
6 Bed 3.5 Bath Sleeps 14
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Pretty Palms - Anna Maria, FL Vacation Rental

Pretty Palms

Anna Maria, FL
3 Bed 2 Bath Sleeps 6
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Sweet Retreat Cottage - Anna Maria, FL Vacation Rental

Sweet Retreat Cottage

Anna Maria, FL
3 Bed 2 Bath Sleeps 8
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414 A Magnolia - Anna Maria, FL Vacation Rental

414 A Magnolia

Anna Maria, FL
2 Bed 1 Bath Sleeps 6
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Sandy's Getaway - Anna Maria, FL Vacation Rental

Sandy's Getaway

Anna Maria, FL
3 Bed 2 Bath Sleeps 8
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LaRaya Retreat - Anna Maria, FL Vacation Rental

LaRaya Retreat

Anna Maria, FL
3 Bed 2 Bath Sleeps 6
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Heavenly Holly - Anna Maria, FL Vacation Rental

Heavenly Holly

Anna Maria, FL
3 Bed 2 Bath Sleeps 6
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Water Colors  - Anna Maria, FL Vacation Rental

Water Colors

Anna Maria, FL
4 Bed 4 Bath Sleeps 10
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Alamanda by the Gulf - Anna Maria, FL Vacation Rental

Alamanda by the Gulf

Anna Maria, FL
3 Bed 2 Bath Sleeps 6
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Mangrove Cottage - Anna Maria, FL Vacation Rental

Mangrove Cottage

Anna Maria, FL
2 Bed 2 Bath Sleeps 5
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About Anna Maria

Treat yourself to a seaside getaway filled with sun-soaked days and easy beach breezes when you pay a visit to Anna Maria. Offering postcard-perfect beaches, easy access to deep sea fishing and ocean adventures, as well as the tranquility of a small town, this hidden Florida vacation destination is perfect spot to let the stress melt away as you slip into vacation mode. 

With family-friendly outings, wonderful nightlife options, and seasonal festivals, there is something for everyone to dive into no matter what time of year you plan to visit our Anna Maria vacation rentals.

Where is Anna Maria, FL?

Located at the tip of Anna Maria Island at the south end of Tampa Bay, you'll be surrounded by the tranquility of swaying palm trees while escaping the typical Florida crowds. An easy drive from Bradenton on the mainland and only 44 miles south of the picturesque shores of Madeira Beach, our Anna Maria vacation rentals have the best of it all!

Things to Do in Anna Maria, FL

Grab a spot underneath one of the beautiful Australian Pines on Manatee Beach and enjoy a bit of lunch before you head out onto the water with a rented stand-up paddleboard. Stroll down the walking path at Coquina Beach and slip into the beach lifestyle, then treat yourself to a bit of shopping at St. Armands Circle.

Grab the famed Anna Maria Island Trolley to one of the local aquariums to learn about the local marine life, then take a water shuttle along the coast to see some dolphins jumping and snap some photos of the sweeping ocean views. Treat yourself to a seaside happy hour and a plate of fresh, mouthwatering seafood while you watch the waves rolling in during sunset.

With a bevy of family-friendly offerings, vibrant nightlife hotspots, and a seemingly endless array of ocean adventures, our Anna Maria vacation rentals put memory-making fun at your fingertips!

Photo Credit: Anna via Flickr 

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