Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals

(17 rentals)
Beautiful 3 Bedroom Townhome Windsor Hills Resort Super Close to Disney & ESPN

3 BR | 3 BA | Sleeps 8 | Quick View

Owner special: Summer's almost over and we only have one week open in August (8/25-9/1)! Ask for 10% OFF!!

$129

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Are you looking for a fully renovated vacation home with a private heated pool, bunk room complete with Playstation 4 gaming system (with games, sound bar, and gaming chair!), in Windsor Hills Resort with its NEW water park, and is very close to Disney World? This is it . . .Name Of Home: The Mouse ...

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Property Type

Kissimmee Townhome

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Enchanted Crystal Castle at Windsor Hills Resort

5 BR | 5 BA | Sleeps 11 | Quick View

Distance to park: 5 miles to Disney World/Animal Kingdom

$185

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

Our Disney vacation villa is furnished to the highest standard and offers your family the luxury of a Five star hotel combined with the relaxed atmosphere of a family vacation home. Soak up the Florida sun on our extended deck where you can relax in the pool and spa, or simply enjoy the shade of the lanai ...

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Property Type

Kissimmee Villa

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Luxury Windsor Hills home: 10 minutes to Disney and steps to the waterpark !

$139

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Don't let our lack of reviews fool you. We are new to but are 5 star rated and reviewed on other platforms. Check out just some of our reviews in the photos!!Summer is booking up FAST. The only available dates left include: Aug 8-17 and Aug 23-31. Don't miss out!!This is definitely the vacation ...

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Property Type

Kissimmee Townhome

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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
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

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 a large family gathering for 2 or even 3 families. ...

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Property Type

Kissimmee Villa

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First Floor 3 Bed 2 Bath Condo

$95

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

You will love this recently updated oversized 1,465 square foot, 3 bed, 2 bath condo. Situated on the first floor for easy access, this condo boasts an amazing location with easy access to the clubhouse, splash park, and pool in the fantastic Windsor Hills Resort. Location is everything, we are just 2.5 ...

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Property Type

Kissimmee Condo

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Toy Story Tower

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 5 miles to Disney World

$243

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Toy Story Tower is an imposing, six bedroom vacation home located within the prestigious gated community of Windsor Hills Resort. Here, you can enjoy the very best in luxurious accommodation all while being located just minutes from Walt Disney World Resort as well as many other great attractions. As ...

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Property Type

Kissimmee House

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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

1

Distance to park: 3 miles to Disney World

$175

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

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 pool and spa in the enclosed lanai but also ...

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Property Type

Kissimmee House

"Will do this again!!"
Reviewed January 15, 2019

We took 5 of our grandchildren to Disney and Universal and one of the best parts of the trip was the house we stayed at! I believe we could have just stayed at the house and still had the time of our lives!

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Disney Adventure Villa at Windsor Hills Resort Sleeps up 16*

6 BR | 4 BA | Sleeps 16 | Quick View

Distance to park: 2 miles to Walt Disney World

$219

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

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 patio area is perfect to watch the sunset, watch ...

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Property Type

Kissimmee Villa

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The Floridian : Ultra Luxuary 5BR Pool Home, 2 Master Suites, Sleeps 12!

$239

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • 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. This is not your typical Rolling Hills house. ...

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Property Type

Kissimmee 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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❤️*Newly Renovated* Luxury 6BR Windsor Hills Pool Villa, 2 miles to Disney

$219

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

LAST MINUTE DEAL AVAILABLE!! ★ NEWLY RENOVATED 6 bedroom 4 bathroom 3500 sqft luxury home, located in famous Windsor Hill Resort, one of best upscale vacation home resort. It’s only 2.5 miles to Disney Theme Park and close to everywhere. It’s the BEST LOCATION!★ This 6 bedroom villa ...

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Property Type

Kissimmee Villa

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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
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

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 has a great south facing view of the wooded conservation ...

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Property Type

Kissimmee House

"Great stay and location"
Reviewed April 30, 2019

House was very clean and beautiful and a great location near the parks. We really enjoyed our stay here.

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Luxury Windsor Hills 3/2 Condo

3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 2 miles to Disney

$79

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

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 Hotel or Resort.Our 3 bed/2 bath (1 king, 1 ...

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Property Type

Kissimmee Apartment

"Pleased"
Reviewed January 24, 2019

I never give a five but this one came close. The owner was very easy to work with and checked on us to see if we made it ok. Tvs need to be larger and each guest needs to leave behind toilet tissue ...

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Luxury TH ( April 6-11)) Close to club house, Free Pool Ht & Welcome Pkg

$110

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

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 town-home with a private pool is perfect for any ...

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Property Type

Kissimmee Townhome

"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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Windsor Hills – Modern Townhome 3 Bed 3 Bath..Free Wi-Fi

$90

per night

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Key Amenities

  • Full Kitchen

About this property

“This new Orlando vacation Townhome has been tastefully decorated, interior design a high standard taking on board the needs of a modern family. This superb villa is located in the gated community Of the prestigious Windsor Hills Resort, which is just off the 192 highway and minutes away from shops, ...

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Property Type

Kissimmee Villa

"AMAZING...HOME, LOCATION, OWNERS. EVERYTHING!"
Reviewed February 3, 2019

We had such great interactions with Andy. Before during and even after the trip. The house was very nice, clean modern and up to date. The house has everything we needed. The resort is beautiful with so ...

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3 Bd 3 Ba Windsor Hills Resort Very close to Disney. Free use Resort Facilities!

3 BR | 3 BA | Sleeps 6 | Quick View

Distance to park: 4 miles to Disney

$105

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

3 Bedrooms 3 Bathrooms Family Room with large HD Cable TV All bedrooms with Flat Screen TVsFormal Dining Room seating 5 plus breakfast bar and outdoor dining Private Pool Patio with Outdoor FurnitureFull-Size Washer/DryerCentral Air Towels and Bed Linens provided Wireless Internet Telephone ...

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Property Type

Kissimmee Townhome

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☀️❤️ Sunshine Memories near Disney: ❤️ by Families

$200

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to Sunshine Memories Villa, where you will have an amazing vacation enjoying all that the Orlando area has to offer. Our 5-bedroom 5-bathroom villa is located less than 10 minutes away from Disney in the beautiful gated resort of Windsor Hills. As you step inside the foyer of your vacation home ...

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Property Type

Kissimmee Villa

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End of the year special--New Waterpark-Windsor Hill Luxury 6B/4B/Pool house

$185

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

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. Web photos here won't be able to show all the beautiful ...

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Property Type

Kissimmee House

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Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals