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Anna Maria Island Rentals with Pools

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1,282 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!

Match: Swimming pool

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Price per night from

$134

Gulf Beach Place - Just a few steps from the Beach

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful, friendly Beach Condo” Beautiful Condo right on the beach with awesome sunsets from the roof and a Dunkin Donuts within walking distance. While the teen/young adult slept in, I visited DD and walked the beach. The owner had a manual that provided lots of activities around the area and places to eat. We enjoyed our stay and would definitely visit again!

Responds fast! avg. 54 minutes

Match: Swimming pool

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Price per night from

$213

Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$207

Dolphin Pointe (North End of AMI!)

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$361

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$172

Blue Bayou

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“"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.

Responds fast! avg. 3 hours 40 minutes

Match: Swimming pool

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Price per night from

$123

90 steps to the Beach!

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing” Absolutely loved our stay! Beautiful condo right next to the beach. Had everything we needed! We will definitely be back!

Match: Swimming pool

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Price per night from

$197

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$305

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.

Match: Swimming pool

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Price per night from

$288

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.

Match: Swimming pool

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Price per night from

$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 13 minutes

Match: Swimming pool

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Price per night from

$550

A Pearl of a Beach Home - now with luxury Saltwater 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 35 minutes

Match: Swimming pool

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Price per night from

$288

Runaway bay 234 bright & clean 1bed /1 Bath Bradenton beach Anna Maria Island

Bradenton Beach condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 12 minutes

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Price per night from

$138

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!

Match: Swimming pool

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Price per night from

$343

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.

Match: Swimming pool

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Price per night from

$373

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 10 minutes

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Price per night from

$447

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 49 minutes

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Price per night from

$209

Anna Maria Island Beach Palms 5B

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$145

Vintage Sunset Cottage Vacation Rental (55 or older park)

Bradenton Beach bungalow

1 bedroom / 1 bathroom / sleeps 4

“Lovely Cottage” This space has been creatively transformed into a comfortable, charming cottage. Jaleen is friendly and quickly responds to questions and provides everything you need. The location is great too!

Match: Swimming pool

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Price per night from

$114

PARADISIAC ENCLAVE 5* Waterfront Canal Pool Home-Dock/Kayak/Bikes/Family fun

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$459

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$573

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 10 minutes

Match: Swimming pool

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Price per night from

$515

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

Match: Swimming pool

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Price per night from

$246

Island Vacation Rental

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Island Paradise” The moment we arrived, exhausted after many delays and problems, the Thomas' home became our home. The condo is well appointed, with comfortable beds, a wonderful kitchen and a fully stocked linen closet, right down to beach towels. Laine, Kevin and Howard are so responsive and saw to all of our needs. Location was prime. We walked to get groceries, eat and do other shopping. There were 7 miles of beaches to explore and the quaint villages of anna Maria and Cortez and Bridge Street kept us occupied when we weren't soaking up the sun. The lanai was my favorite place to drink my coffee and check out the action at the pool each morning . We ate the majority of our meals there, under the twinkling lights. It was a wonderful month!

Responds fast! avg. 3 hours 12 minutes

Match: Swimming pool

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Price per night from

$147

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$247

Gladiolus on the Water

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 55 minutes

Match: Swimming pool

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Price per night from

$339

Anthony Beach Cottages Bare Feet Retreat

Holmes Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$257

Anna Maria Island Beach Palms 7A

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$148

Anna Maria Island Beach Sands

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Paradise” We loved this place, felt right at home the minute we walked in the door. Had a view minor problems and the service to deal with them was awesome. Thanks Terry for a great experience, being our first time here on anna Maria Island. If we didn't need the extra bedroom, we would have booked for next yr. Location~~!! wow, close to great restaurants Love the view...can't say enough of the sunsets and of course the dolphins, got chills every time I seen them, almost daily...first class...thanks...

Match: Swimming pool

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Price per night from

$182

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“A trip to paradise.” From the breathtaking views of both the Gulf and the Bay to the wonderful, eclectic furnishings, this condo is everything one could hope for. It has great amenities for entertaining friends and every convenience you will need. The heated pool overlooks the Gulf and allows direct access to the beach and the elevator provides ease in getting up to the condo. This vacation was the most enjoyable I've ever experienced.

Responds fast! avg. 3 hours 20 minutes

Match: Swimming pool

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Price per night from

$383

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Famous Holiday” Everything was so perfekt ... WE CAME back next Year THE HOUSE BEAUTIFUL AND CLEAN.. THE Area perfekt

Match: Swimming pool

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Price per night from

$264

Anna Maria Island Beach Sands 201

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$190

Runaway Bay unit 192 bay view 2bed/2Bath - Bradenton Beach - Anna Maria Island

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 46 minutes

Match: Swimming pool

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Price per night from

$165

Lifestyle on the island

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$128

Holmes Beach Family Home w/Private Pool & 3 Decks!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$238

GULF COAST DESTINATION

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 6 minutes

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Price per night from

$144

Mintfish, beautiful views across Bimini Bay! 4-Bed

Anna Maria Island villa

4 bedrooms / 4 bathrooms / sleeps 8

“Great View!” The best thing about this home is it's location on Bimini Bay. Beautiful pool and view out over the bay. The home is decorated in a happy motif, although the beds were deemed hard as boxes by a couple of our guests. Kitchen is sufficient for cooking basics, and has nice appliances. Overall a nice stay on a quiet, north end spot of the island.

Match: Swimming pool

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Price per night from

$418

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$408

Viewing 38 of 1,282
rentals in Anna Maria Island

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