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Anna Maria Island Rentals with Pools

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1,553 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

$139

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. 6 minutes

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Price per night from

$344

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. 1 hour 28 minutes

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Price per night from

$206

Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

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Price per night from

$190

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 0 minutes

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Price per night from

$243

AMI Bradenton Beach Ground Condo

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$145

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$217

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 34 minutes

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Price per night from

$298

Bright and cheery waterfront home with private pool and spa

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$441

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

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$174

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

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$332

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.

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Price per night from

$93

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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Price per night from

$229

Coconuts Beach Front 106 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$196

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

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$270

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$175

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!

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Price per night from

$198

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

$308

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$184

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

$203

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 3 minutes

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Price per night from

$132

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 22 minutes

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Price per night from

$430

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 17 minutes

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Price per night from

$281

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

$497

Coconuts Beach Front 107 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$308

Update One Bedroom/One Bath with view and steps to beach unit 234 runaway bay

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$111

Absolutely Perfect - Cove at Sandy Pointe #207

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$93

Coconuts Poolside Unit 104

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“The BEST spot on the island!” 24 hours ago we got home from our vacation to Anna Maria at the Coconuts! I'm already wishing we could get a plane and head back!! We absolutely love this island.. And finally lucked out finding the perfect place to stay! We rented a pool side room which was perfect for my family! My daughter couldn't wait to get up and jump in the pool at 9am and just a few steps walk out of the pool gate was the GULF! The location could not be better. The beach wasn't busy like around the public entrances we have previously been on. We could even cast out our poles and catch fish while we enjoyed the beach. My 8 year old daughter caught 5 fish right off the bat Saturday morning! The actual room was great too! Very old school Florida beach feeling to it.. It really felt like the island life! If your looking for a top of the line updated place.. This wouldn't be your place. But if your just looking for that true island feeling.. It's here! It has everything you could possibly need on a condo.. Other then a washer and dryer, but they are on site and I was able to come home with clean luggage to put away! The only complaint we have is the beds.. They were not comfortable at all. Doing our full 10 vacation on those would have been tough. The pricing was VERY reasonable also.. A lot of places on the island can get pricey. The Resort on all was awesome tho! We love it.. And we will be back next year

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$160

Anna Maria Island "High End" Vacation Rental

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$347

Coconuts Beach Front 109 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$196

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

Bradenton Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Excellent accomodation and locality” This is the second time we have stayed here, in different units. Everything was excellent. No fuss, and just so convenient with the trolley at the roadside and the beach a walk across the road

Responds fast! avg. 3 hours 38 minutes

Match: Swimming pool

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Price per night from

$231

Coconuts Two Bedroom Unit 117 Upstairs Courtyard

Holmes Beach villa

1 bedroom / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 57 minutes

Match: Swimming pool

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Price per night from

$196

Dog-friendly home with private pool, great location near beach, shopping, dining

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$121

Coconuts Beach Front 105 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 57 minutes

Match: Swimming pool

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Price per night from

$196

Coconuts Two Bedroom 118 Upstairs Courtyard

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$196

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 47 minutes

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Price per night from

$427

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

$231

Viewing 38 of 1,553
rentals in Anna Maria Island

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