Vacation Rentals & Beach Rentals in Anna Maria Island

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418 beach rentals

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

Match: Private outdoor pool (heated)

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Price per night from

$397

Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 24 minutes

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$194

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 39 minutes

Match: Private outdoor pool (heated)

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$258

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 39 minutes

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$567

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 39 minutes

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$792

Bright and cheery waterfront home with private pool and spa

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (heated)

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Price per night from

$330

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 21 minutes

Match: Private outdoor pool (heated)

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$294

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 39 minutes

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$313

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 39 minutes

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$249

**PARADISE RETREAT IN BRADEN RIVER LAKES**

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 10

“Just like being at home.” Great location very quiet neighborhood, Close to grocery, gas, restaurants. We were 30 minutes to an hour from different beaches, we visited 3, Clearwater, Anna Marie Island and Siesta Key. Then we could come back to relax in the pool it was great. Very roomy home would difinetly stay here again.

Responds fast! avg. 42 minutes

Match: Private outdoor pool (heated)

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$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 39 minutes

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$202

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 39 minutes

Match: Private outdoor pool (heated)

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$282

'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 49 minutes

Match: Private outdoor pool (heated)

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Price per night from

$297

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

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. 46 minutes

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$533

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 39 minutes

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$188

Anna Maria Island "High End" Vacation Rental

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 4 minutes

Match: Private outdoor pool (heated)

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$343

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!

Responds fast! avg. 3 hours 35 minutes

Match: Private outdoor pool (heated)

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Price per night from

$228

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

$422

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

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$359

5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 24 minutes

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Price per night from

$399

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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$184

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

Anna Maria Island house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

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$497

High-end home w/ private pool & spa, courtyard, & floor-to-ceiling windows

Anna Maria house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (heated)

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Price per night from

$356

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 20 minutes

Match: Private outdoor pool (heated)

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$286

Luxury waterfront home w/ private pool and dock only three blocks to beach!

Anna Maria house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (heated)

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Price per night from

$497

Incredible, dog-friendly house with private heated pool, close to the beach!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$287

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 47 minutes

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Price per night from

$457

$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. 3 hours 53 minutes

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Price per night from

$319

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

Anna Maria Island house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

Match: Private outdoor pool (heated)

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Price per night from

$497

Ah this is it v2.0! Lemon Cottage w Pool!! Relax!!

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

“Way more than we expected!” Our week at Lemon Cottage was just excellent! Owner, Chris, has thought of everything we would need for the beach. The house is lovely inside, and landscaped just as nicely outside. We used the two bikes to explore, and we took many walks. The lanai area, with pool, is so inviting, that we managed to spend many hours out there just relaxing and trying to decide why we needed to move on to any activity at all! One of the things we did was to take a boat trip with Captain Kim (which I had done before). We stopped at the low places in the bay at low tide and held many live sea creatures...a great trip for adults as well as children. Mote acquarium is also high on my list, and they also have an educational boat tour of Sarasota Bay. Ringling mansion tour and grounds was lovely as well, even though we were caught in a deluge of rain. Lemon Cottage was indeed a lovely place to spend a week and we are hopeful that we will be able to stay there again. I highly recommend it!

Match: Private outdoor pool (heated)

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Price per night from

$200

Stunning luxury newly constructed beachfront villa

Anna Maria villa

4 bedrooms / 5 bathrooms / sleeps 8

“Fabulous beach house” After a mad week doing the theme parks in Orlando we came here for some serious relaxation - and what a great choice it was. The house is stunning and the location couldn't be bettered. Living on the beach meant we could be up for early morning shell hunts and then have evening strolls to the Sandbar for cocktails on the sand watching the glorious sunsets. We saw dolphins, manatees, rays and pelicans. The pool area got a lot of use - a nice shady retreat and good fun for our boys - but most of our time was spent outside. There are lots of lovey restaurants to walk to - the Waterfront, the Sandbar, the two pier restaurants - and you can walk there on the sand. Still picturing the crystal clear sea, sunny skies and white sand. Magical.

Match: Private outdoor pool (heated)

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Price per night from

$802

Crescent Wave

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

“Absolutely wonderful!!” This house is even better than it looks in the pictures .... everything you might want or need while on vacation is provided. It was extremely clean, and the location is perfect. The center across the street is a real bonus with "snow bird" deals. The pool and backyard of this house are beautiful, with plenty of seating and heated pool. We had an issue with the heat in the pool and owner, Rick, responded asap and got it repaired the same afternoon. He then followed up to make sure everything was working. House is very well-stocked from the kitchen to the pool, with lots of beach equipment provided as well. And the two master suites on either end of the house are very convenient.

Responds fast! avg. 1 hour 23 minutes

Match: Private outdoor pool (heated)

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$241

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. 2 hours 57 minutes

Match: Private outdoor pool (heated)

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Price per night from

$229

Full duplex w/ private heated pool and fenced backyard - dogs welcome!

Anna Maria house

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (heated)

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Price per night from

$529

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!

Responds fast! avg. 2 hours 26 minutes

Match: Private outdoor pool (heated)

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Price per night from

$266

A Lime Cottage Pool beach house..Ahhh this is it!!

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 6

“Love, love, love the Lime Cottage!!!” Well, where do I start? We absolutely loved out stay at the Lime Cottage. We felt immediately comfortable and at home upon arrival. Chris is an incredibly thoughtful and organized host. From not having to deal with keys to every amenity in the cottage you could possibly want in vacation getaway place. The whole place was very clean, decorated so well and created an extremely relaxing atmosphere. The beds were perfect and comfortable and everything worked! We thoroughly enjoyed making meals there and hanging out at the wonderful pool. We named the pool cleaner R2D2-14! Walking to the beach was a treat as is was so close. We enjoyed The Beach House Restaurant and Sharky's which are both walkable. The island is easy to get around and tends to relax you even more with it's built-in pace! We managed to play golf, go to a Hockey Game and take in a Baseball Game. Chris had plenty of maps and lots of information about the surrounding areas and activities to take in. No difficulties finding your way around. We managed to split the difference and spent a fair amount of time at the cottage as well away from it. By the time we came to the end of our stay, we all did not want to leave. We were quite comfy and could of easily stayed longer. On that note, I will say; we will definitely come back to this precious place. Chris and family, thank you for making this a wonderful experience Cheers Kellie & Bruce

Match: Private outdoor pool (heated)

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Price per night from

$196

Colorful beach cottage with private pool, grill area, & more - dog-friendly!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (heated)

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Price per night from

$196

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