Vacation Rentals & Beach Rentals in Anna Maria Island

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3,494 beach rentals

Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$207

The Peninsula Clermont, Orlando

Clermont villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent Vacation! Can't wait to go back” We absolutely loved your villa and the resort it was situated in. From the moment we arrived we enjoyed every minute. The house was very quiet and spacious. It can easily fit in two families of 4. The house was clean inside out. The mattresses were plush and bedding soft. The Mickey/Minnie room was super cute and my kids' favorite! We all slept like babies every night. The furniture was solid wood and looked brand new. It was also nice to have a kitchen with anything and everything we needed. It's a paradise to have that much space for a vacation. All theme parks including the Lego land were easy to access. There were Publix, McDonald, Danny's close by with plenty of choices to eat out. We were not able to swim in the pool or check the clubhouse. Will try out next time. The view from the backyard was gorgeous! We would definitely be back again soon. I would be happy to refer any friends thinking of travelling to Orlando area.

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Price per night from

$131

Responds fast! avg. 3 hours 10 minutes

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Price per night from

$287

⭐Great Value Villa w/ Private Pool - Nearby Disney Resort⭐

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

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Price per night from

$265

Disney, Universal, Beaches, Golf, New Rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$218

Bella Vida New Phase 6 bedroom Modern Home

Kissimmee house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$321

“Great Family Memories” We give this home an A+!! Everything about it from the appearance, to the owner (Liz), to the location, and the management company combine to give you unprecedented good customer service that insures a great experience. Everything is geared towards you! The house is actually even nicer than the pictures depict!! We had 5 adults and one child stay and there was plenty of room for everyone. We loved the layout. Our granddaughter squealed with delight when she saw the Mickey Mouse room. She even asked to go to bed several nights!! We enjoyed going to nearby outlet malls, Disney, Disney Springs, restaurants close by, and even grilling out on the patio while family members swam in the pool. The game tables in the garage provided some lively competition. The greatest compliment you can give a place is to say you would return again. When we come back to this area again, Pilgrim's Paradise will be at the top of our list to stay at again! Liz made everything run smooth and was a delight to work with!! Thanks for sharing your beautiful villa with our family!!

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$189

Unique 5 Star Home - Private Pool, Free SOLAR Pool heat, WIFI, BBQ, Disney

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Violet lane” Home was clean and charming.We enjoyed the pool and privacy greatly. Owner thought of most anything we may need, except one; toilet paper. This was our first time staying in a private home rather than a hotel so perhaps it isn’t a given but if we had known, it would have saved us an immediate trip to store. I cannot speak for other guests but felt that not starting laundry, despite stating was not mandatory, not doing so may affect my deposit. A few other minor issues: missing ping pong table, “key?” to working slot machines, how, or if, the ice maker worked and where the garage door opener was located(we did find on the furnace in the garage the day before we left), and whether the swinging chair was safe to use, despite the crack, may have been problems easily remedied with a phone call but ultimately not important enough to bother owner and take time away from us. Not meant to be a negative review, it is not. Overall, we had a lovely time and would stay again. However, it seemed important to be honest in regard to our experience.

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Price per night from

$149

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Price per night from

$331

“Very welcoming and worth it !” Me and my family absolutely loved this vacation house everything was so welcoming and near perfect ! This house is definitely something we will never forget and hopefully when we come back we will be able to rent from kim molnar again ! Everything was to a T ! Thank you so much kim !

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Price per night from

$458

Dis Oasis Villa at Windsor Palms Resort - Close to Disney!

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

“Wonderful house for a large family group” The beds were comfortable, the house was immaculate and our needs were taken care of instantly by the owner. Close to shopping, restaurants and Disney World parks.

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Price per night from

$400

Oakhill Disney Villa

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 8 minutes

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Price per night from

$194

Bella Piazza Condo

Four Corners apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$155

Windsor Palms 4/3 Pr. Pl., Hot Tub, Jacuzzi/Games

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing house!” We have amazing family time! This house is excellent with great location! We'll be back soon! I recommend

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Price per night from

$177

Luxurious Resort Condos minutes from Disney World with full access to all

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 10 minutes

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Price per night from

$103

Championsgate 138

Davenport house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$259

SR015V: 9 Bed, Treehouse, Avengers, Ping Pong

Four Corners house

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 20

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Price per night from

$401

Luxury Disney Dreams Home Pool Spa Game Room

Kissimmee house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$358

20% OFF Sale Prime Location. Heated Pool, Game Room, Grill, near Disney World

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$182

SR013V: 9 Bed, Avengers, Frozen, Ping Pong

Four Corners house

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 20

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Price per night from

$403

Encore Resort 6 Bedroom Home with Pool (1913)

Reunion house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 59 minutes

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$215

Solara Resort 135

Four Corners house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 21

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Price per night from

$332

Amazing Villa with south facing pool and conservation view

Orlando villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$228

Championsgate 318

Davenport house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$316

SR007V: 9 Bed, Star Wars, Toy Story, Ping Pong

Four Corners house

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 20

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Price per night from

$313

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Price per night from

$264

Highlands Reserve 37

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$204

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Price per night from

$265

SR006V: 8 Bed, Incredibles, Fashionista, Pool, Shuffle Board

Four Corners house

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$452

Solara Resort 151

Four Corners house

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

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Price per night from

$342

Encore Resort 8 Bedroom Home with Pool (2114)

Reunion hotel apartment

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 59 minutes

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$252

Championsgate 49

Davenport house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$332

Storey Lake Resort 311

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$332

W261: 10 Bed, Rapunzel, Jurassic Park, Avatar, Sports Arcade

Reunion house

  • 10 bedrooms
  • 13 bathrooms
  • sleeps 26

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$1,219

W318: 9 Bed, Avengers, Aladdin, Superhero Arcade

Reunion house

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 24

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Price per night from

$1,251

2300sq ft, Luxury 5 Bed, 4 Bath Villa w/Pool, 15 mins to the Disney Gates!

Four Corners house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$218

SR016V: 9 Bed, Social Media, Pandora, Ping Pong

Four Corners house

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 20

Match: Private outdoor pool (unheated) Table tennis

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Price per night from

$354

Bella Vida Resort 5 Bedroom Home with Pool (1870)

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 15

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$211

Viewing 38 of 3,494
rentals in Anna Maria Island

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