Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals

(13 rentals)
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Goofy’s Getaway

5 BR | 5 BA | Sleeps 10 | Quick View

1

$245

avg/night

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Key Amenities

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

About this property

Goofy’s Getaway is a stunning five bedroom vacation home located at Windsor Hills Resort in sunny Central Florida. Here, you and your family can enjoy the very best in luxurious and stylish living combined with the convenience of being located just minutes from Walt Disney World Resort and many ...

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Property Type

Kissimmee Villa

"Outstanding rental"
Reviewed April 29, 2021

We rented this home as our first vacation home rental. I can definitely say we will return. Ray and Eileen have an amazing home that they offered to us for 10 days. Nothing was wrong and if it was I am ...

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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

6

Distance to park: 3 miles to Disney World

$235

avg/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

"Girls Trip 2020"
Reviewed July 24, 2020

My friends and I absolutely loved this home ...it was perfect for the 8 of us. I WOULD DEFINITELY RENT AGAIN!!

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Toy Story Tower

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 5 miles to Disney World

$245

avg/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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Sunshine Memories Villa. ☀️❤️ Magical Family Retreat near Disney w/Waterpark

$298

avg/night

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Key Amenities

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

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

"Don’t worry, be happy"
Reviewed August 7, 2020

Even with all that’s going on, this was a blessing in disguise. Really needed this and everything was perfect. You can’t live your life in fear, just be cautious in all you do. No complaints whatsoever. ...

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

$250

avg/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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Luxury Windsor Hills 3/2 Condo

3 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to park: 2 miles to Disney

$107

avg/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

"Excellent resort facilities"
Reviewed March 24, 2020

Resort was excellent with all the Disney attractions. Plus all the restaurants nearby and the Walmart store just one half mile away. The pool area was very large and accommodated all the guests. Very well ...

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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

$350

avg/night

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Key Amenities

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

About this property

COVID 19 INFO UPDATED ON OUR WEBSITE, CANCEL FOR ANY REASON TRAVEL PROTECTION COVERAGE OFFERED, FLEXIBLE CHANGES.PLEASE SEE RATE NOTES FOR RATES FOR VARIOUS SEASONS AND SIZE HOMES 4-6BR Private pool homes in Windsor Hills resort and other resorts available. All homes this size include private pool, ...

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Property Type

Kissimmee House

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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

$199

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

$228

avg/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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Livin' Free2❤️NEW Sparkling Clean! Closest Resort WDW/ESPN

6 BR | 4 BA | Sleeps 16 | Quick View

Distance to park: 2 miles to Disney

$287

avg/night

View Details

Key Amenities

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

About this property

Clean NEWLY Renovated. NEW Air Conditioned Game Room!! Close .3 mile to the FREE Water Park & across from the big playground!! We have 2 homes side-by-side for larger groups and a 3rd home just a few doors down.* just 2 miles to Disney * Private Heated Pool & Spa * FREE Water park * Foosball, ...

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Property Type

Kissimmee House

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Enchanted Crystal Castle at Windsor Hills Resort

5 BR | 5 BA | Sleeps 12 | Quick View

1

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

$223

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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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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

$114

avg/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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MY DISNEY CASTLE, Private Pool, Games Room, Family Friendly, Baby Equipped Home

$502

avg/night

View Details

Key Amenities

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

About this property

* LOCATED 3 miles from the Disney World Theme Parks*KEY-LESS entry with personalized access code is provided to each guest for enhanced security. Home Security Alarm with 24/7 monitoring for added security.* FREE Welcome starter items provided, including 1 roll of Paper Towels, Toilet Paper in ...

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Property Type

Kissimmee Villa

"Perfect home for a family!"
Reviewed January 16, 2021

My family and I stayed late December 2020 into early January 2021. Family of three, including a four year old. This house was perfect for our daughter!! Aside from the themed bedrooms and the AMAZING pool ...

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Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals