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Anna Maria Rentals with Pools

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1,500 beach rentals in Anna Maria with pools

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

“We love this house and Mark is wonderful!” The house and pool were clean with everything you need and the location was great too! Mark was very nice to deal with! I wish we could have met him personally!

Responds fast! avg. 6 minutes

Match: Swimming pool

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Price per night from

$343

Beautiful, well-maintained home w/private pool - walk to beach, dining, & more!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$332

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$217

Waterfront and dog-friendly home with private pool, dock, views, and lanai!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$243

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 34 minutes

Match: Swimming pool

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Price per night from

$299

Gorgeous views,spectacular home!

Anna Maria house

5 bedrooms / 3 bathrooms / sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

Responds fast! avg. 1 hour 6 minutes

Match: Swimming pool

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Price per night from

$430

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 45 minutes

Match: Swimming pool

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Price per night from

$400

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 19 minutes

Match: Swimming pool

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Price per night from

$412

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 45 minutes

Match: Swimming pool

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Price per night from

$457

Crescent Wave

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

“Mrs.” With three couples and three kids, this house met our needs perfectly. Great location-about three blocks from the beach, and two blocks from Pine Avenue. We didn't have to get back in the car after arriving until we left. The house was well stocked with towels, kitchenware, and even books and games for the kids. The wagon, beach buggies, beach chairs, and beach toys from the shed were all put to good use. Having a pool with three kids is a must. We enjoyed the pool area, but the pool needed some TLC. All and all it was a great vacation. We would stay at this house again!

Responds fast! avg. 1 hour 48 minutes

Match: Swimming pool

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Price per night from

$241

The Oleander House

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$360

Reduced rates for June Stunning luxury beachfront house with pool and spa

Anna Maria villa

4 bedrooms / 5 bathrooms / sleeps 8

“Fabulous beach house” After a mad week doing the theme parks in Orlando we came here for some serious relaxation - and what a great choice it was. The house is stunning and the location couldn't be bettered. Living on the beach meant we could be up for early morning shell hunts and then have evening strolls to the Sandbar for cocktails on the sand watching the glorious sunsets. We saw dolphins, manatees, rays and pelicans. The pool area got a lot of use - a nice shady retreat and good fun for our boys - but most of our time was spent outside. There are lots of lovey restaurants to walk to - the Waterfront, the Sandbar, the two pier restaurants - and you can walk there on the sand. Still picturing the crystal clear sea, sunny skies and white sand. Magical.

Match: Swimming pool

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Price per night from

$826

Beautiful cottage w/ private pool - walk to the beach, dining, and Bayfront Park

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$249

Gladiolus on the Water

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$280

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Match: Swimming pool

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Price per night from

$256

Dog-friendly house w/ private lagoon pool - two blocks from the beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$249

Paradise Cottage

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$219

Haupia House

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$255

AMI Du Soleil

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$304

Vibrant Beach House – Private Pool and Steps to the Beach

Anna Maria house

4 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$261

Manatee Manor

Anna Maria house

1 bedroom / 2 bathrooms / sleeps 6

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Price per night from

$280

Coconut Bayou - a gem with heated pool on a fantastic location in Anna Maria

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$236

Aquaville A - 2/1 beauty with private pool in the heart of Anna Maria. Pets!

Anna Maria apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$143

Seashell - Less than 1 minute to the beach - PRIVATE POOL and PET friendly!

Anna Maria condo

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$229

Spring Break

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$304

Tarpon Pointe

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$280

Bayside condo w/ a shared pool - close to the beach & restaurants

Anna Maria house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$115

Spacious gulf side home with private pool and views of gulf beaches.

Anna Maria house

4 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$411

Bay-facing condo w/amazing view, shared pool & beach across street

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$169

Canary Cottage

Anna Maria house

2 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$280

213 75TH STREET

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$312

C-viewFlorida, Canal/Dock/Heated Pool/Near Gulf - A Hidden Gem

Anna Maria house

5 bedrooms / 4 bathrooms / sleeps 10

“Great Beach Vacation Spot” A really outstanding vacation house. The house is roomy, up-to-date in every way, and clean beyond all means. It has everything you need if you want to cook and if not you are very close to great resturants. You are a short hop to a beautiful beach. But you also have your own swimming pool and dock-bring your boats or whatever. The place was extremely clean upon arrival and was easy to find. Just a great place for a vacation.

Match: Swimming pool

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Price per night from

$590

Dog-friendly home w/ private pool in quaint neighborhood

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$257

WAVES EDGE ANNA MARIA

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$1,089

Manatee Cottage

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$314

215 SPRING AVENUE

Anna Maria house

4 bedrooms / 4 bathrooms / sleeps 14

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Price per night from

$773

Coastal Cottage - NORTH END 3 bedroom, 2 bath pet friendly pool home!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$185

Island Priva-Sea

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$336

Viewing 38 of 1,500
rentals in Anna Maria

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