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Anna Maria Rentals with Pools

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1,338 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

$340

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

$334

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

$221

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

$277

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 26 minutes

Match: Swimming pool

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Price per night from

$295

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 17 minutes

Match: Swimming pool

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Price per night from

$432

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 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

$451

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 46 minutes

Match: Swimming pool

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Price per night from

$463

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 27 minutes

Match: Swimming pool

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Price per night from

$243

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.

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Price per night from

$687

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

$250

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 51 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

Match: Swimming pool

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Price per night from

$287

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

$298

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

Match: Swimming pool

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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

Responds fast! avg. 3 hours 32 minutes

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

Responds fast! avg. 3 hours 32 minutes

Match: Swimming pool

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Price per night from

$229

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

$134

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

Anna Maria house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$413

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

$155

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.

Responds fast! avg. 1 hour 11 minutes

Match: Swimming pool

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Price per night from

$576

Dog-friendly home w/ private pool in quaint neighborhood

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 8 minutes

Match: Swimming pool

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Price per night from

$248

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

Match: Swimming pool

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Price per night from

$185

Sea Pearl - on the Canal in Anna Maria with heated pool. Pet friendly!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 32 minutes

Match: Swimming pool

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Price per night from

$240

Bayside condo w/ shared pool - across the street from the beach

Anna Maria house

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$140

Jacaranda Beach House - one minute walk to the beach! Private Pool

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

Match: Swimming pool

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Price per night from

$257

ANNA MARIA'S BEST LOCATION! PANORAMIC VIEW of Pool Dock & Bayou to Gulf

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 47 minutes

Match: Swimming pool

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Price per night from

$430

Aquaville B - a 3/1 beauty with pool in the heart of Anna Maria, pet friendly

Anna Maria apartment

3 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 32 minutes

Match: Swimming pool

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Price per night from

$158

50 Steps to the Beach!

Anna Maria condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$203

Cherryfish, a spectacular spacious 4-bed home!

Anna Maria villa

4 bedrooms / 3 bathrooms / sleeps 8

“Great home, great location!” This home was wonderful for our two families of four. Plenty of space for everyone and the pool was perfect. The only complaint we had was the cleanliness upon arrival, there was long black hair everywhere and the overly fluffy rug in living room had food and garbage stuck in it, which the crawling infants would find each day. The rug was shedding green fuzz everywhere, rug needs to go! It also seemed there must have been pets on the sectional couch at some point, all of us had allergy symptoms when sitting on the couch, even the kids. Otherwise we were very happy with the house itself and location of property and proximity to beaches!

Match: Swimming pool

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Price per night from

$469

"Island Oasis" A single family North end canal home with pool

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 48 minutes

Match: Swimming pool

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Price per night from

$383

Old Island Charm - Newly Renovated

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$429

THE SALTY DOG ON NORTH SHORE

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 59 minutes

Match: Swimming pool

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Price per night from

$261

Bay View Dream Waterfront Home

Anna Maria house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 59 minutes

Match: Swimming pool

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Price per night from

$271

COPACABANA BOATERS DREAM HOME

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 59 minutes

Match: Swimming pool

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Price per night from

$281

Great rentals within 20 miles that match your search

Penthouse Condo At Riverstrand Golf & Country Club

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$79

Short Term Fully Furnished Condo 1Bedroom

St. Petersburg condo

1 bedroom / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$97

Viewing 38 of 1,338
rentals in Anna Maria

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