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Houses Anna Maria Island

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457 houses

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 4

“Even better than you can imagine!” We are so thrilled to have discovered this gem. Barb really has thought of everything you need for a perfect vacation - short or long stay. Quaint boutique shops, excellent dining - one of the best "Lobstah" dinners ever, and a beautiful beach with all the comforts of home - literally right around the corner.

Responds fast! avg. 1 hour 1 minutes

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$150

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

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$341

Spacious house w/ private yard & great location near the beach - dogs ok!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 17 minutes

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$130

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 45 minutes

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$228

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

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$329

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

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$215

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 29 minutes

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$205

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 16 minutes

Travelers’ Choice award

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$230

Ohana Hale North 2 Bedroom on Anna Maria

Holmes Beach house

2 bedrooms / 1 bathroom / sleeps 6

“Home is very comfortable and we really enjoyed our stay” Home is very comfortable. Loved the kitchen and owners could not be more accomadating.

Responds fast! avg. 1 hour 38 minutes

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$178

Holmes Beach Home w/Pool & Hot Tub, Walk to Beach!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

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Price per night from

$305

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 23 minutes

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$295

Sunny, dog-friendly cottage w/ a spacious patio and grill, steps from the beach!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

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$196

Ohana Hale South West Suite

Bradenton Beach house

2 bedrooms / 1 bathroom / sleeps 6

“Great place for a family Stay” We stayed for 5 days in June. Very clean and comfortble close to the beach and quiet. Excellent experience. We left some items there and they were even shipped to us promptly.

Responds fast! avg. 1 hour 38 minutes

Travelers’ Choice award

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$178

Luxury 3 Bedrooms/3 Full Baths, Private Heated Pool with Waterfall, Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Christmas at the Beach” It was a wonderful family vacation for two families going away for Christmas! There were 4 adults and 6 children! The pool was amazing and the house was perfect! Anna Maria Island is gorgeous and the house is in a perfect location for the beach, food and shopping! The owners were available for any needs that needed to be met! Awesome Owners!

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$228

Sea Haze Cottage - Gorgeous waterfront pool beachhouse

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

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$357

19 Palms. Quaint Old-Florida Charm

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 59 minutes

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$172

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. 2 hours 36 minutes

Travelers’ Choice award

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$430

Bermuda Bay Club betwn the Beach and Bay , elevator, nicely furnished

Bradenton Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Excellent condo with elevator for all the ladies” Sharkey's Bar and Grill was by far the bet prime rib around. Sandbar had the best fish platter and Skinny's the best burgers and the City Pier Restaurant had great shrimp overall excellent food all around.

Responds fast! avg. 3 hours 6 minutes

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$279

The Lime Door

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

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$300

Dog-friendly condo w/ beautiful upstairs deck and grill, steps from the beach

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 36 minutes

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Price per night from

$201

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 40 minutes

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Price per night from

$400

Longboat Key, Waterfront 3BR w/ Private Enclosed Pool & Spa - Near Beach!

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$359

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 21 minutes

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$463

Spectacular Beach House With GulfView Only Steps to a Pristine Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

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$431

A Pearl of a Beach Home - with luxury private heated pool and hot tub

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“out standing place to stay” I would/will stay here again when we come back down. Everything is top notch and the home has everything you need. We enjoyed the pool and hot tube, used it every night. Mike and Lesley are very easy to work with and do anything to make things go smoothly.

Responds fast! avg. 1 hour 25 minutes

Travelers’ Choice award

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Price per night from

$260

4102GD-10. Beautiful Anna Maria 1 Bedroom Condo

Anna Maria Island house

1 bedroom / 1 bathroom / sleeps 4

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$395

4102GD-6. Modern 2 Bedroom Condo with Pool and Patio

Anna Maria Island house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$648

$300 OFF MARCH PARADISIAC ENCLAVE 5* Waterfront Canal Pool Home-Dock/Kayak/BikeS

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 39 minutes

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Price per night from

$345

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 40 minutes

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$457

Affordable Anna Maria Vacation - close to everything

Holmes Beach house

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 50 minutes

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Price per night from

$92

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

Travelers’ Choice award

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$241

Anna Maria Island Stunning Waterfront home

Anna Maria Island house

3 bedrooms / 2 bathrooms / sleeps 7

“Fantastic accommodations and hosts!” As others have stated, the pictures do not do this home justice! The common space is allocated in such a way that there are four different conversational areas and an office! This was a working vacation for me and I sincerely enjoyed working from the indoor office area or poolside. I cannot say enough about the attentiveness and graciousness of our hosts, the Greenfelders. From the time I spoke with Gail to make the reservation, I knew we would be instant friends. My feelings were confirmed upon meeting her in person. My husband and I enjoyed a wonderful social evening with Glen and Gail during our visit and every concern we had while staying at the house was addressed in a timely fashion to our complete satisfaction. I don't really want others to know about this home as I'd like to keep it for our own personal jewel, but I guess that wouldn't be fair...so rent this house!

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$279

4102GD-5. Renovated 2 Bedroom Condo with Private Pool

Anna Maria Island house

2 bedrooms / 2 bathrooms / sleeps 6

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$598

Charming 2 Bedroom/2 Bath Cottage on a Canal

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

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$327

Charming condo w/shared tennis courts & pool - steps to the beach

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 5 minutes

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Price per night from

$134

1304BDN-R. Anna Maria Island Retreat is a Gorgeous Two Bedroom Condo

Anna Maria Island house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$892

Coquina Sands, view beach from balcony, priv pool

Holmes Beach house

2 bedrooms / 3 bathrooms / sleeps 6

“Great place, great location, great vacation” We stay at Anna Maria for 12 days and if we could we would be there for 12 years. Awesome place and great host. Everything was ready for us. Only high marks. Thanks

Responds fast! avg. 3 hours 6 minutes

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Price per night from

$228

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 36 minutes

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Price per night from

$265

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