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Anna Maria Island Rentals with Pools

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1,073 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

“Great Value Stay in Paradise aMI!” This is a lovely spacious condo, nicely furnished, with decent wifi, aircon and all mod cons. The condos in the Sandy Point complex all share a pool and we found this to be very clean, nicely warm and never too crowded. Although it's on the quieter side of the island we liked the location - it's a five minute walk from Publix, even less to the free Island Trolley Bus, and less than 10 minutes to the beach for those amazing sunsets :-) The equipment cupboard allowing us to borrow beach chairs, swimming noodles, buckets and spades etc was much appreciated. Having looked around at other rentals we found this condo to be very keenly priced. Andrew and Jo were very pleasant and easy to deal with and we will definitely stay again some day.

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Price per night from

$133

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

Bradenton Beach apartment

3 bedrooms / 3 bathrooms / sleeps 6

“Great place, great location, and everything you need!” We stayed here to go to my sister's wedding at The Beach House. We loved this townhouse. It had spacious rooms, beautiful decor, and a great view of the ocean from the balcony. I was really impressed with how many little things were available. There were plenty of towels, soap and shampoo dispensers in the bathroom, spices in the cabinet, beach towels, and even aloe gel for burns. In the garage there is an area full of sand toys and floats and a grill. We felt so comfortable and had a true vacation.

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Price per night from

$263

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 46 minutes

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Price per night from

$123

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$196

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

$344

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.

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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. 3 hours 52 minutes

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Price per night from

$1,621

Bermuda Bay Club Un09 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.

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Price per night from

$263

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 18 minutes

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Price per night from

$400

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. 3 hours 27 minutes

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Price per night from

$156

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$629

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 0 minutes

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Price per night from

$476

Anna Maria Island Beach Palms 5B

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$232

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 49 minutes

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Price per night from

$218

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

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$442

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. 1 hour 44 minutes

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Price per night from

$178

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$246

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 18 minutes

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Price per night from

$515

Anthony Beach Cottages Bare Feet Retreat

Holmes Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$258

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

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Price per night from

$287

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

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$344

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

$279

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. 3 hours 27 minutes

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Price per night from

$188

Anna Maria Island Beach Palms 7A

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$194

Gladiolus on the Water

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$404

Lifestyle on the island

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$144

Anna Maria Island Beach Sands 201

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$294

Come join us for your Winter Migration!!!!!!!!!!

Bradenton Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$66

Anna Maria Island Beach Paradise 6

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$212

Castnetter Beach Resort 5

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$315

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.

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Price per night from

$384

Contemporary Beach House, Very Private Yard & Pool - 1.5 Blocks to Beach

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 47 minutes

Match: Swimming pool

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Price per night from

$287

Anna Maria Island Beach View 207

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$203

Anthony Beach Cottages Gulfview Condo

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$258

Gorgeous Remodeled Townhouse between the BeachnBay

Bradenton Beach townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 0 minutes

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Price per night from

$263

GULF COAST DESTINATION

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 24 minutes

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Price per night from

$201

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$287

Anna Maria Island Absolute Anna Maria-Private Beach Access-Heated Pool-Wi-Fi

Anna Maria Island apartment

2 bedrooms / 2 bathrooms / sleeps 5

“A little gem” Lovely condo, great views and ideally situated for restaurants and shopping (all within walking distance). Would definitely come back again.

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Price per night from

$257

Viewing 38 of 1,073
rentals in Anna Maria Island

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