Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals

(14 rentals)
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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

$100

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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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

6

Distance to park: 3 miles to Disney World

$265

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

$272

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pets allowed
  • 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

"Vacation"
Reviewed August 3, 2021

The house was beautiful and very clean and spacious, the pool was a little to hot, had to contact owner to lower the temperature in the jacuzzi and pool also the pool speaker did not work, owner stated ...

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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

1

Distance to park: 2 miles to Disney World

$300

avg/night

View Details

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 up to 31 days prior to arrival. **Due to the number of inquiries we receive, you are welcome to send an inquiry through this page but please allow a day for us to respond, for faster reply, ...

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Property Type

Kissimmee House

"Perfect"
Reviewed July 17, 2021

The owner was excellent with communication and the my family loved the house. My room was beautiful and the garden tub was magical definitely will rent from David again

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Toy Story Tower

6 BR | 4 BA | Sleeps 14 | Quick View

1

Distance to park: 5 miles to Disney World

$255

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

"June vacation"
Reviewed July 8, 2021

House was very nice and clean. Really no problems but the hot tub piece had to be ordered for heat that we paid for extra but it was ok because it was hot enough outside. We stay at wondsor hills every ...

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Goofy’s Getaway

5 BR | 5 BA | Sleeps 10 | Quick View

1

$255

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

$292

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 Oasis - Relaxing 5 bedroom, 5 bath pool home

5 BR | 5 BA | Sleeps 12 | Quick View

1

Distance to park: 2 miles to Walt Disney World

$286

avg/night

View Details

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 with new mattresses. 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 ...

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Property Type

Kissimmee House

"Wonderful"
Reviewed July 22, 2021

The house was amazing my family and I love it. I will definitely rent again. The staff from Florida rentals were great their service was wonderful. I will recommend to my family and friends thank you ...

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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

$365

avg/night

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

$316

avg/night

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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

"Wonderful Time at My Disney Castle!!"
Reviewed July 23, 2021

We cannot say enough great things about our stay at My Disney Castle! Wonderful themed rooms, great pool, and great experience with owner! Owner was ALWAYS available whenever we had any questions… We ...

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

$238

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

"Family Vacation"
Reviewed July 14, 2021

My family stayed at this property from July 1-9 the house was clean upon arrival and the check in process went smooth. The owner was great to work with and handled any problems or concerns that we had during ...

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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

$120

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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★ Minutes to Disney ★ Private Pool ★ Water Park Included! ★ Windsor Hills ★

$184

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pool
  • Private pool

About this property

Magic Holiday HouseA fabulous home-base for your Orlando Vacation! Minutes to Disney Parks. At the end of the day, you get to come back and relax in your own private townhouse/ pool or go to the resort pool & let the kids tire themselves at the water park. All the space and comforts you'd find ...

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Property Type

Kissimmee Townhome

"Loved it."
Reviewed August 21, 2021

Beautiful House, and a wonderful experience from start to finish! Cant wait to go back! The home was spacious and beautifully decorated and Lisa was a Pleasure to work with, and very helpful.

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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

$285

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pets allowed
  • 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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Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals


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