Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals

(23 rentals)
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6 BR | 4 BA | Sleeps 12 | Quick View

8

Distance to park: 3 miles to Disney World

$360

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Perfect for our family"

Located a couple miles from Animal Kingdom and close to other Disney World attractions, the home was perfect for 3 generations of our family. It is spacious and well appointed. The kids loved the private ...

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6 BR | 4 BA | Sleeps 14 | Quick View

4.8 rating on other travel sites

$501

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"What a delightful home! It exceeded all of our expectations...There was a television in almost every room, two living rooms with comfortable seating, coffee bar, game room, fun children's bedrooms with a "secret room", pool with large movie screen, and plenty of outdoor loungers and seating...I ...

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Property Type

Kissimmee House

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6 BR | 3.5 BA | Sleeps 14 | Quick View

4.8 rating on other travel sites

$500

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Something for everyone - fun, beauty, and comfort. There's so much to love! Everyone will love the incredible Avengers game room; it is like no other. Plus, all will love the heated pool and spa. Kids will love the themed bedrooms. And, adults will love the professionally decorated beauty of the ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

5.0 rating on other travel sites

$480

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

ARE YOU LOOKING for a just renovated beautiful vacation home that is full of fun? This is it . . . Avenger theme game room - South facing (plenty of sun) private saltwater pool and spa - Poolside movie theater - Themed kids bedrooms - And much more. Also, it's located in Windsor Hills Resort - the closest ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

4.9 rating on other travel sites

$509

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"When you walk through the front door, you immediately walk into fun with the adult area's pool table and large TV. And that's just the beginning. There's an awesome game room, 3 themed bedrooms, and in the pool area are a poolside theater and bar counter with TV. You will be totally entertained ...

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Property Type

Kissimmee House

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5 BR | 5 BA | Sleeps 10 | Quick View

4.8 rating on other travel sites

$413

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"We loved staying at this house, it is in a convenient location to the parks, and groceries are nearby. The house was clean and well-equipped. Our grandkids really enjoyed the themed rooms, the game room, and of course the pool! The gated resort community is awesome, and the water park/big pool were ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

4.8 rating on other travel sites

$509

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Have lots of fun and relax in this beautifully renovated vacation home in Windsor Hills Resort! The air conditioned Star Wars themed game room (with a life-size Storm Trooper) and the poolside movie theater and bar make this home a one-of-a-kind." Cindy CARE YOU LOOKING for lots of fun ...

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Property Type

Kissimmee House

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5 BR | 5 BA | Sleeps 12 | Quick View

5.0 rating on other travel sites

$487

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"We just got home from our 1 week stay and are already wishing we were back! The home was beautiful and looked just as pictured in the listing. We were very close to the parks and shopping but yet felt like we were secluded. The neighborhood is wonderful and was great for walks. The pool and game ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

5.0 rating on other travel sites

$438

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"We have stayed in many Windsor hills homes and this is THE one to stay in! Beautifully decorated, fun and so comfortable!" Beth MARE YOU LOOKING for a very special vacation home? This is it . . . Totally renovated by a professional decorator and includes an incredible game room, a private ...

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Property Type

Kissimmee House

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4 BR | 4 BA | Sleeps 8 | Quick View

Distance to park: 2 miles to Disney

$274

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Wonderfully Themed villa in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy complimentary pool & spa heat, themed rooms, and a fun games room in the garage (air hockey, ping ping, foosball)! This is one of very few 4-bedroom units on the resort. We're nice and close ...

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Property Type

Kissimmee Villa

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5 BR | 5 BA | Sleeps 12 | Quick View

4.9 rating on other travel sites

$408

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Spacious, well-equipped, clean and a quick drive to the Disney parks. Great game room. You couldn't ask for anything more!" Melissa MARE YOU LOOKING for a vacation home with an incredible game room, a private south facing pool and SPA, totally renovated home, in Windsor Hills Resort with ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

4.9 rating on other travel sites

$465

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"This was an ideal spot to relax and enjoy what Florida has to offer. The bedrooms were comfortable and clean. The theater room was great for adults and kids to enjoy movies and video games. Would definitely stay here again!! " Cynthia TARE YOU LOOKING for a beautiful totally renovated ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 12 | Quick View

4.7 rating on other travel sites

Distance to park: 2 miles to Disney World

$453

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Welcome to Oasis by KLMJ Sunshine! Completely renovated (2022), this villa is in the #1 location in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy complimentary pool & spa heat, themed rooms, and the only private Virtual Reality studio in the area! This is the 2nd ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"perfect family villa"

The location is great near all the attractions. The pool and hot tub were wonderful. The beds were very comfortable. The bathrooms were very well kept It was just a wonderful place to stay. We will visit ...

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3 BR | 2 BA | Sleeps 6 | Quick View

4.8 rating on other travel sites

Distance to park: 2 miles to Disney World

$179

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Escape by KLMJ Sunshine! This is a completely renovated 3-bedroom condo in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy the massive heated pool, brand new water park, large playground, tennis and basketball courts, mini-golf, arcade, movie theatre, fitness ...

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Property Type

Kissimmee Condo

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5 BR | 5 BA | Sleeps 12 | Quick View

2

Distance to park: 2 miles to Walt Disney World

$286

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Terrific 5-bedroom/5-bathroom rental home owned by firefighters and 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 ...

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Property Type

Kissimmee House

"Disney get away"

Had a great time at this property love location definitely recommend.The clubhouse at this resort was really well-maintained and we had a great time

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Family vacation"

We had the best time at My Disney Castle. Our kids spent most of their days in the house’s pool and hot tub. We paid for pool heat and it was so worth it. The pool and hot tub were so warm! It was great. ...

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5 BR | 5 BA | Sleeps 12 | Quick View

1

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

$463

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • 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"

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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6 BR | 4 BA | Sleeps 16 | Quick View

2

Distance to park: 2 miles to Disney

$391

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Great House, Great Hosts"

Our stay at this resort home was absolutely perfect! There was more than enough space for my family of 5 as well as my brother in law and 2 nieces. The kitchen was very well stocked with everything we needed ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Just 5 minutes away from Disney World, this Cozy, Lux, themed townhouse will be your perfect getaway from Disney while being your neural operation center to Disney, Golf and Orlando itself. Equipped with everything you need to have unforgettable vacations, from a fully equipped Kitchen to cook the best ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

A fabulous home-base for your trip to Orlando! Just Minutes to Theme Parks.Home Features:* 3 Bedrooms* 1 King, 1 Queen, 2 Full, 1 Twin (Sleeps 7-8) * All New Mattresses * TV's in every bedroom * USBs & Outlets convenient for charging* 3 Bathrooms* All En-Suite * Hair ...

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Property Type

Kissimmee Townhome

"Loved it."

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Welcome to our beautiful townhome, located in prestigious Windsor Hills Resort, only 2 miles to the Magic of Disney World. Home offers 2 queen & 2 single beds (3rd bed/bath with 2 single beds locked (unlocked occasionally at no charge). Open space living/dining room has a TV/DVD player to enjoy a ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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"

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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Windsor Hills Resort (Kissimmee, Florida) Vacation Rentals