Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals

(20 rentals)
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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Windorhills townhome/pool/New Water Park/1.5 mile to Disney

$105

per night

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Key Amenities

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

About this property

3 bedrooms, 3 full bathrooms, sleeps 7 Disney Dream Vacation Home offers the best combination of service, convenience, comfort and affordability.-Service- this vacation home is serviced by a large local property management group, which ensure you will have the quickest service response.-Convenience- ...

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Property Type

Kissimmee Townhome

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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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RB203: A LUXURY STAR WARS EXPERIENCE, POOLSIDE! 4 mi from WDW

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 4 miles to Walt Disney World

$100

per night

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Key Amenities

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

About this property

MISSION: Use the Force to experience an intergalactic vacation like no other! Join the Rebel Alliance at this magnificent 3 bedroom, 2 bathroom condominium that overlooks the multi-million dollar water park and splash pad at the world renowned Windsor Hills resort. This Rebel Base has been completely ...

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Property Type

Kissimmee Condo

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Luxury Windsor Hills 3/2 Condo

3 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to park: 2 miles to Disney

$69

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

"Great time had by all."
Reviewed February 15, 2020

Pool,perfect games room. Wonderful home clean plenty of towels bedding, utensils and such overall great experience great gathered community.

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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

4

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

"Very, nice and closed to Disney"
Reviewed January 8, 2020

Es muy céntrico y muy callado y seguro el lugar además limpio y la recepción muy amables en todo momento

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The Floridian Oasis - Relaxing 5 bedroom, 5 bath pool home

5 BR | 5 BA | Sleeps 12 | Quick View

Distance to park: 2 miles to Walt Disney World

$175

per night

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Key Amenities

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

About this property

Terrific 5-bedroom/5-bathroom rental home located in Windsor Hills Resort. This beautiful villa includes upstairs and downstairs King Bedroom suites. It also has a Queen Bedroom, Twin Bedroom and sleeper sofa on the first floor. And there is an another Twin Bedroom on second floor making this home ideal ...

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Property Type

Kissimmee House

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

Inquire for rates

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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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❤️*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

"Great stay! Definently recommend."
Reviewed November 15, 2019

My family and I had a great stay. Beautiful house. The kids love the rooms. Definitely would stay again in the future.

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Renovated Home with Private West Facing Pool and close to Amenities

$232

per night

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Key Amenities

  • Air Conditioning
  • Pool
  • Private Pool

About this property

Are you looking for a vacation home that has been beautifully renovated with a west facing private heated pool/spa, in Windsor Hills Resort with its NEW water park, and is very close to Disney World? This is it . . .Name Of Home: Blue Bridge Villa At Windsor Hills Location: Windsor Hills Resort ...

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Property Type

Kissimmee House

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Mickey’s Magical Villa

4 BR | 4 BA | Sleeps 8 | Quick View

$185

per night

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Key Amenities

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

About this property

Our vacation villa has four bedrooms all with in suite bathrooms and is equipped with all the comforts of home but comes with the convenience of being situated less than two miles from Disney World.Mickey’s Magical Villa is a fully furnished luxury family vacation home located in Windsor Hills ...

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Property Type

Kissimmee House

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Windsor Hills resort Private Pool Home (FREE WATER PARK USE DURING STAY!)

6 BR | 3.5 BA | Sleeps 14 | Quick View

Distance to park: 2 miles to Disney World

$226

per night

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Key Amenities

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

About this property

4-6BR Private pool homes in Windsor Hills resort like this one. All homes this size include private pool, spa and wifi, full kitchen, large living spaces, at least 3 bathrooms and most include game room. Please ask for specific homes available for your dates, or visit our website! (we also have condos ...

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Property Type

Kissimmee House

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Beautiful 3 Bedroom Townhome Windsor Hills Resort Super Close to Disney & ESPN

$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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First Floor 3 Bed 2 Bath Condo near Disney

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to park: 3 miles to Walt Disney World

$95

per night

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Key Amenities

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

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

"Amazing location for Disney"
Reviewed October 23, 2019

This condo was simply amazing. The room were so clean and everything was so put together. The rooms were nicely decorated and the beds were super comfy! With the kitchen stocked with everything to cook ...

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Just updated in June 2019! Only 4 miles to Disney World!

6 BR | 4 BA | Sleeps 14 | Quick View

1

Distance to park: 7 miles to Disney World

$250

per night

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Key Amenities

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

About this property

Wishes & Dreams Villa is a perfect Disney area retreat! This home offers all the comforts your family expects and goes much further: beautiful new flooring throughout; well appointed, yet inviting kitchen; all new beds & bedding. Every spacious area professionally decorated & furnished--your ...

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Property Type

Kissimmee House

"Beautiful Home!"
Reviewed August 27, 2019

We had such a great time! This home is spacious, comfortable, beautifully decorated, and clean! It is also conveniently located for all things Disney and beyond! We highly recommend this home for any ...

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Enchanted Crystal Castle at Windsor Hills Resort

5 BR | 5 BA | Sleeps 11 | Quick View

1

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

$199

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

"Wonderful home and resort"
Reviewed December 6, 2019

This home was super clean and there was so much room. The two kids rooms upstairs are amazing. My kids were in heaven. The game room was so much fun. Always nice to be able to come back after a day at ...

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March 5- 14 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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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

$108

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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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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Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals