Crestwynd Bay Rentals

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118 Houses

Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great Stay” The house was a better option than hotel rooms. The house was very clean and they had everything necessary for a pleasant stay. They also provided pool towels for the pool or jacuzzi. The jacuzzi was nice and hot and a good option in the evening. Each bedroom had a TV and they had a pool table in the garage. It's a quiet neighborhood. It's not far from Disney or Walmart for groceries.

Responds fast! avg. 2 hours 44 minutes

Match: Private outdoor pool (heated)

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Price per night from

$121

“A Magical Stay” What's not to love about this home! First and foremost Brandie herself is a genuine person who really cares about the people who stay at her home. From the initial contact of a personal phone call, to her follow ups on every little question, to her wishing us a safe trip to a thank you and welcome home at the end, Brandie is truly a great family person! The home itself was as described in other reviews and more. The location to the clubhouse could not have been better. A short walk down the path (100yds maybe) and the kids were relaxing by the lagoon pool! The added security of a gated community provided additional piece of mind even though you are only 5mins from Disney. The staff at the community became like family before we left. Friendly, cheerful, always willing to stop and talk about anything and everything! The home itself is exactly as pictured! Clean and comfortable made for it enjoyable to return home for afternoon breaks from the park. The Disney bedroom was the room of choice for our youngest! The downstairs bedroom provided a nice separation for our oldest to have her space when exhaustion took over:). We have rented homes before when traveling to Disney and Brandie's is at the top of the list! From location, ease of access, amenities, cleanliness, comfort and exceptional (what I will call) customer service and value, you won't find a better place to stay or person to work with then Brandie and her home!!! We will definitely be back again!!! Thanks Brandie :)

Match: Private outdoor pool (heated)

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Price per night from

$228

Sweet Escape

Windsor Hills townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private outdoor pool (heated)

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Price per night from

$166

Wow Factor-Interior Designers Own 5 bed/5bath Home

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$224

Disney Memories. Beautiful 4 Bedroom, 3 Bath,

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 57 minutes

Match: Private outdoor pool (heated)

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Price per night from

$172

Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 33 minutes

Match: Private outdoor pool (heated)

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Price per night from

$247

Beautiful 6BR/4BA villa, Pool/Spa, 2miles2Disney

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

“Excellent Review” This is a beautiful home very nice surroundings we enjoyed the stay will rent again. The kids enjoyed the pool area and the water park located a block away.

Match: Private outdoor pool (heated)

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Price per night from

$321

Pineapple Paradise with Private Pool in Windsor Hills by Notable Vacation Rental

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Good location, townhouse had everything we needed.” The townhouse was conveniently located for us. We went to Disney one day, downtown Orlando twice for Citrus Bowl events. We had a minor issue with what was referred to as "drain flys"... but it was quickly addressed. I would go back to this property.

Match: Private outdoor pool (heated)

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Price per night from

$201

Windsor Hills Greenview 5BR/5BA All-Suite Pool/SPA 2 Miles to Disney

Four Corners villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

Responds fast! avg. 1 hour 32 minutes

Match: Private outdoor pool (heated)

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Price per night from

$219

“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 !

Match: Private outdoor pool (heated)

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Price per night from

$459

Relax and Enjoy

Kissimmee house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

Match: Private outdoor pool (heated)

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Price per night from

$545

5 Star Family Home with Water Park, Private Pool, Hot Tub 2 Stoplights to Disney

Four Corners house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

“Perfect for everyone's needs and in an excellent location!” From long before we arrived we knew how excellent a villa this was, as the owner and the management team were so incredibly helpful and willing. Including the management team assisting me with purchases to go in the home before I arrived and Susan the owner answering all my crazy questions! In fact I'm going to miss our email chats! On arrival in the home we found everything perfectly clean tidy and in order with an excellent welcome pack to see us through before our big shop. Being a mum of young children I was delighted with the huuuge washing machine and dryer. We need these in the UK. The children loved the pool and the games room and spent lots of happy times there, as did the adults after the kids had gone to bed. We unusually chose not to hire a car and we got around no problem. Disney, particularly animal Kingdom is only a short distance away and universal is only about 25-30 mins. I prebooked a lot of journeys with a company called happy limo who were absolutely outstanding in their punctuality and ease of booking. Anyway back to the house, every bedroom was perfectly appointed with all you could need. The living areas were very spacious even with 7 adults and 2 children. We never once felt on top of each other. The shop and communal pool at Windsor hills is a nice short stroll away and Windsor Hills itself is very clean, well laid out and very secure indeed. I could not recommend this house highly enough and am very pleased I chose this one. I spent weeks and weeks searching villa rentals before settling on this house so I learnt a lot about the different features and prices of villas and I do feel that this one fitted the bill perfectly.

Match: Private outdoor pool (heated)

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Price per night from

$315

Mickey's Magical Villa

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$344

Beautiful Vacation Villa Close to Disney

Kissimmee house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 47 minutes

Match: Private outdoor pool (heated)

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Price per night from

$287

Dream family vacation rental villa

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

Match: Private outdoor pool (heated)

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Price per night from

$281

Pooh's Palace in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$516

✪ 5min→Disney Spacious Family Villa ✪ 135

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$103

Gorgeous Family Villa! 114

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$103

⭐️ 5min→Disney Cozy Villa | BBQ Grill ⭐️ 108

Kissimmee house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$109

☀ Beautiful Family Villa BBQ patio 5min ---> Disney| ♥ 137

Kissimmee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated)

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Price per night from

$103

★Fantastic Townhome | 5min→Disneyworld |★ 134

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$109

WH_604BR Windsor Charm

Four Corners house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$164

⭐ Sensational Large 7 Bedroom Home with Pool,Hot Tub,Games Rm, 5 Min Disney ⭐

Four Corners house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated)

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Price per night from

$402

⭐️Amazing Family Villa ⭐️ 5min→Disney | BBQ | 128

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Match: Private outdoor pool (heated)

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Price per night from

$126

Gorgeous 3bd villa close to Disney (WH557)

Four Corners villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$1,146

FG_800BR Sunset Mansion

Kissimmee house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 20

Match: Private outdoor pool (heated)

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Price per night from

$707

Match: Private outdoor pool (heated)

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Price per night from

$247

★ 5min→Disney Family Villa | Hot Tub | BBQ ★ 127

Kissimmee house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$103

My Disney Castle, Windsor Hills Pool Villa located 2 miles from Disney

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$430

♥ 5min→Disney Family Villa | BBQ ♥ 104

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$103

Disney Escape

Four Corners house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

Match: Private outdoor pool (heated)

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Price per night from

$206

♥ 5min→Disney Wonderful Villa | BBQ | 102

Kissimmee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$115

⭐️ 5min→Disneyworld Precious Townhome| BBQ ⭐️131

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$111

★Amazing Hidden Gem | Min ➡️ Disney | ❤ 139

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Match: Private outdoor pool (heated)

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Price per night from

$103

6BR/4B Villa, Pool, 2 Miles from Disney World

Four Corners house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$377

♥ 5min to Disney Amazing Villa| BBQ & Hot Tub | 110

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$109

✧5min→Disney✧Fantastic Family Villa✧ 113

Kissimmee house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$115

☀5min➡️Disney Precious Villa| BBQ & Hot Tub ⭐️132

Kissimmee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$103

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rentals in Crestwynd Bay

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