Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals

(13 rentals)
Enjoy our 3000 square foot, custom luxury pool home

$239

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool

About this property

Enjoy our three-thousand square foot, custom luxury pool home, less than four miles from Disney World. We offer two master suites with king-size beds (one with Jacuzzi), two queen-bedrooms, one twin-bedroom, and queen size pullout-couch, all on one floor. ...

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Location Information

Kissimmee, Florida, 34747

Property Type

House

"Our Dream Vacation"
Reviewed July 30, 2018

This home was PERFECT for my family! It was very spacious and had everything we needed to make us comfortable. Very close to Disney and close to a lot of nice eating places we could not have chosen a ...

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Snow White Villa Close to Disney World

Snow White Villa Close to Disney World

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 2 miles to Disney World Resort

$200

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed

About this property

We offer a luxurious decorated home close to Disney World Resort. Kid friendly house, with plenty of things to do in the house. The house is very close to Orlando Disney World Resort. It has 6 bedrooms and 4 bath. There is plenty of space to accommodate ...

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Location Information

Kissimmee, Florida, 34747

Property Type

Villa

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2 Miles to Disney World. 6 BR with Private Pool & Spa. Fireworks Views

2 Miles to Disney World. 6 BR with Private Pool & Spa. Fireworks Views

6 BR | 3.5 BA | Sleeps 14 | Quick View

1

Distance to park: 2 miles to Disney World

$165

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Kid Friendly

About this property

Windsor Hills 6 Bedrooms. 2 Miles to Disney. Perfect Floor plan for Multi-familyWe invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your ...

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Location Information

Kissimmee, Florida, 34747

Property Type

Villa

"Happy and pleased"
Reviewed August 30, 2018

My family stayed at Alexander vacation homes just a week ago and we couldn’t have been more pleased with our accommodations or service. The home was spacious, super clean, well equipped with everything ...

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August special--New Waterpark-Windsor Hill Luxury 6B/4B/Pool house

$185

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Kid Friendly
  • Managed by Owner
  • Free WiFi

About this property

Large 6 Bedroom Executive Vacation Home With 2 Themed Kids Rooms, Sleeps 14 Disney Dream Vacation Villa is located in the #1 rated upscale five-stars Windsor Hills Resort at the doorstep of Disney world.This property was newly thoroughly renovated. ...

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Location Information

Kissimmee, Florida, 34747

Property Type

House

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THE HAVEN AT WINDSOR HILLS RESORT 5 BED POOL HOME

$195

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

The Haven is an executive home overlooking the woodland conservation area in Windsor Hills resort community located only two miles from the entrance to Walt Disney World. Enjoy five bedrooms, five bathrooms and an excellent games room.Windsor Haven ...

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Location Information

Kissimmee, Florida, 34747

Property Type

House

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South facing heated pool and spa

South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

Distance to park: 3 miles to Disney World

$145

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

Situated in the Window Hills resort community about 2 miles from Disney, this 6-bedroom, 4-bath vacation rental home specializes in providing fantastic Florida vacations! With 2,812 square feet and accommodations for 14, guests can enjoy not only the private ...

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Location Information

Kissimmee, Florida, 34747

Property Type

House

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Luxury Windsor Hills 3/2 Condo

Luxury Windsor Hills 3/2 Condo

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 2 miles to Disney

$79

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Communal Pool
  • No Pets Allowed
  • Free WiFi

About this property

Windsor Hills is one of the greatest gated community located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. Windsor Hills has all the amenities of a Five Star ...

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Location Information

Kissimmee, Florida, 34747

Property Type

Apartment

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Affordable Luxury for Your Family by Disney

Affordable Luxury for Your Family by Disney

3 BR | 2 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Disney World

$67

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed

About this property

Windsor Hills is an oasis only a mile from Disney World. Amenities include a huge pool with a water slide, clubhouse, playgrounds, exercise room, putting green, sports area, convenience store and shuttles to major attractions. AAA gives it a 3 diamond ...

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Location Information

Kissimmee, Florida, 34747

Property Type

Condo

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Olaf’s Endless Summer at Windsor Hills Resort

Olaf’s Endless Summer at Windsor Hills Resort

4 BR | 4 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to 2.5 miles to Disney World

$149

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

Book directly on our website provided in the link to the right. All nights are $149 - this is an amazing deal! We have the best vacation rental prices in Windsor Hills, the #1 rated vacation resort near Disney World. We even provide free Pool Heat.Welcome ...

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Location Information

Kissimmee, Florida, 34747

Property Type

House

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Windsor Hills Orlando Villa 6 Bedroom Villa only 2 miles to WDW

$165

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Kid Friendly

About this property

Our Windsor Hills Orlando Villa Features a saltwater pool. The salt water chlorination produces clean, clear, silky-smooth water that’s luxuriously soft. It is also a continuous natural sanitization method, in contrast to administering harsh chemical ...

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Location Information

Kissimmee, Florida, 34747

Property Type

House

"Amazing vacation!"
Reviewed September 21, 2018

The property we stayed as was very nice friendly staff. Always prompt if i needed anything. Will be returning.

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3 Bed 2.5 Bath POOL Townhome Windsor Hills Resort!

$85

per night

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Key Amenities

  • Hot Tub
  • Communal Pool

About this property

Located in the beautiful gated resort community of Windsor Hills, a firm favorite for repeat visitors. The home comes fully furnished and equipped with everything you will need to enjoy your stay here in sunny Florida, it even has it’s own private ...

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Location Information

Kissimmee, Florida, 34747

Property Type

Town Home

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Luxury TH ( Oct 27-Nov 3) Close to club house, Free Pool Ht & Welcome Pkg

$110

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed

About this property

'Disney Dreams Vacation Homes is a spacious Orlando vacation town home in the heart of the exclusive Windsor Hills resort community, less than 2 miles from Disney in Orlando, Florida. With 3 bedrooms and 3 bathrooms, this fully air-conditioned, stylish ...

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Location Information

Kissimmee, Florida, 34747

Property Type

Town Home

"It has everything,"
Reviewed March 18, 2018

We will definitely stay here again. Lots of amenities and personal touches. The fully equipped kitchen and stores - Walmart minutes away saved us quire a bit of money as we were able to prep our own foods ...

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Disney Adventure Villa at Windsor Hills Resort Sleeps up 16*

Disney Adventure Villa at Windsor Hills Resort Sleeps up 16*

6 BR | 6 BA | Sleeps 16 | Quick View

Distance to park: 2 miles to Walt Disney World

$219

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

Beautiful 3500 Square Feet of Luxury Our spacious family villa features 3500 square feet of luxury living space with 6 bedrooms and 4 bathrooms which can accommodate 16 comfortably. Our South facing screened in swimming pool with hot tub and a covered ...

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Location Information

Kissimmee, Florida, 34747

Property Type

Villa

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Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals