Anna Maria Island Rentals with Pools

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Filtering by: Swimming pool

1,405 beach rentals in Anna Maria Island with pools

Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful condo, close to everything!” Everything was perfect in the condo which was new and updated! The 2 new full size beds in the 2nd bedroom were too hard. The pool was a nice size and stayed sunny most of the day. Shopping was close and the city beach also was close. We would drive down the road to our favorite stretch of the beach. I would definitely stay here again, very quiet location off the beaten path, but not far from it! Love the beach chairs, towels, cooler, umbrella, pool toys, and more provided!

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Price per night from

$110

Gulf Beach Place - Just a few steps from the Beach

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

“Outstanding Condo” The perfect place to stay on AMI! Close to everything and very safe. Will be going back to this condo for sure. Been staying on AMI for 4 years and found the hidden gem.

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$150

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

“Amazing Oceanview Pool Home and Perfect Location On Anna Maria Island” Let me first say that Mark (the home owner) exceeded any and all expectations for our 15th wedding Anniversary! We booked last minute and when we wanted to stay an additional day Mark rescheduled planned maintenance in order to accommodate us. When we arrived there were fresh flowers, wine, cookies, music and a Anniversary Cake for us! The Beautiful ocean view pool home is in a perfect location on Anna Maria Island and equipped with everything you will need: floats for the pool, anything you would need to take to beach across the street, bikes to explore the island, a large kitchen stocked with everything you need to cook, very comfortable beds and spacious rooms, fresh orchids throughout the home, library of DVD's and books, and I could just keep going...make sure you take the bikes and explore - go to the Museum, to bean point, have fresh grouper sandwich at the Rod and Reel Pier, ride down to Two Scoops for an ice cream and take a walk on the City Pier, on Fridays at 12:30 you can pick up amazing fresh bread at Olive Oil Outpost with some other goodies, go have a custom snack at the Donut Experiment, A drink at the Sandbar Rest., Lunch or Dinner at the Waterfront is amazing, and more all a short bike ride away. All my wife and I can say is what a wonderful week and we will be back for sure!

Responds fast! avg. 7 minutes

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Price per night from

$112

Canalfront home w/ pool, dock & lanai - 2 blocks to the beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$258

runaway bay 2 bedroom condo with wonderful access to restaurant, beach, shopping

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$174

Dog-friendly cottage w/ private heated pool - minutes from beaches & more!

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$328

Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$187

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$321

Oceanfront dog-friendly home w/private pool & ocean view - right on the beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$714

Bright and cheery waterfront home with private pool and spa

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$321

AMI Island Living -Walk to Beach-Ground Level Unit

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$174

AMI Bradenton Beach Ground Condo

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$144

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$212

Blue Bayou

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

“"Home from Home"” A very well appointed apartment in a great location that had everything you would wish for to enhance your vacation experience. A real home from home that is clean, well furnished and spacious. The owners have been great to deal with and nothing is too much trouble. I have already recommended this accommodation to friends who were similarly impressed and we will be staying here for the third time later this year.

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Price per night from

$144

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. 3 hours 38 minutes

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Price per night from

$165

Pet-Friendly Holmes Beach Home - Steps to Beach!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$296

Breezy canalfront home w/ pool & dock - 3 blocks to Bean Point Beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$203

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$173

Bermuda Bay 1467

Bradenton Beach condo

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$192

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 50 minutes

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Price per night from

$296

**PARADISE RETREAT IN BRADEN RIVER LAKES**

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 10

“Summer Vacay” We had a wonderful stay. Everything was perfect and Rhonda was super helpful. The home was about 30 minutes from the beach and the pool was a blessing, that's where the kids wanted to stay. I would book this home again without a second thought.

Responds fast! avg. 56 minutes

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Price per night from

$133

Upscale tropical getaway with private pool & spa, elevator, and more!

Holmes Beach house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$180

Anthony Beach Cottages Island Retreat

Holmes Beach house

4 bedrooms / 4 bathrooms / sleeps 8

“Family friendly” My family and I enjoyed our stay in Florida and we all loved being able to be under one roof again. My mothers dream was to take us 6 kids, now adults, to the ocean again. Also, she wanted her two new grand-sons to see the ocean fir the first time. Her dream was made reality staying at a beautiful beach house only 1 1/2 blocks from the beach. The beach access was beyond beautiful and as close to your own private beach, for at this time of year there was no crowding. The pool at the house was great for cooling off after a day at the beach and the pool room had several toys and floating devices for the kids to use. The house was fully stocked with towels for multiple days and the washer and dryer came in handy with babies around! The living room seating was great for a big family to gather around for late night discussions and the kitchen stocked with basic appliances for cooking and cleaning.The only thing that could have made the stay better, was a little comfier mattresses in the bedrooms. However the case, this beach house was a cherry on top to my family's short fall vacation to Florida!

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Price per night from

$345

744 Jacaranda Rd

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

“Nice getaway” Nice home! Large enough for family. Decks and heated pool were great!

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Price per night from

$315

Charming house with private heated pool, patio, and grill - steps from beach

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$258

'Elegance' 100 Steps from the Beach!

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing!” This house has it all and a perfect location makes it an even more wonderful place to vacation. We hope to be back soon!

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$298

Coconuts Beach Front 106 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$253

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

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 8

“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!

Responds fast! avg. 2 hours 11 minutes

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Price per night from

$235

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

2 bedrooms / 2 bathrooms / sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$133

NEW LISTING! Great condo w/shared pool & access to beach, shopping & dining

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$218

Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453

Bradenton Beach apartment

3 bedrooms / 3 bathrooms / sleeps 6

“great place for florida vacation” the location was great, 180 degree views of the beach and water. manager Dan was very helpful and accomodating. condo was modern, spacious and well laid out for our family of 4 adults and 3 kids. kitchen was huge and well equipped pool was practically private. parking ample and mostly covered. beach chairs were in need of updating and perhaps too readily available for non-residents. perfect vacation for swimming, beach walks and shell hunting. plan to stay again if possible.

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Price per night from

$196

Bradenton Beach Club A

Bradenton Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Very nice Condo” This condo is lovely, a beautiful porch on the gulf, and 3 good sized bedrooms and 2.5 baths. The pools in the ocmplex are very nice, as is the boardwalk to the bay. Very nice location in Bradenton Beach. And people at rental office very helpful. Only slight negatives are the state of applicances. They are all ver old, and not too many. It is obviously used only as a rental, there are no "home touches", such as reading lamps for the twin bed room, and the coffee pot is very old and tempermental. But overall the building and unit are lovely.

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Price per night from

$409

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 10 minutes

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Price per night from

$286

Absolutely Perfect - Cove at Sandy Pointe #207

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 7 minutes

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Price per night from

$121

Charming, dog-friendly duplex with a shared pool and a Key West-style deck!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$188

Dog-friendly house with private pool, island views & nearby beach access!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$153

Coconuts Beach Front 109 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$254

Gulf-front condo w/ balcony & shared heated pool - steps to the beach & trolley!

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$95

Viewing 38 of 1,405
rentals in Anna Maria Island

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