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Windsor Hills Villa Near Disney with Heated Pool & Game Room

Photo gallery for Windsor Hills Villa Near Disney with Heated Pool & Game Room

An aerial view of a resort with multiple swimming pools, a water park, and surrounding buildings. - Windsor Hills Villa Near Disney with Heated Pool & Game Room (Kissimmee)
A living room with a large flat-screen TV, a coffee table, blue sofas, and a view of a swimming pool. - Windsor Hills Villa Near Disney with Heated Pool & Game Room (Kissimmee)
A spacious indoor area with tiled flooring, multiple seating arrangements, ceiling fans, and large windows allowing natural light. - Windsor Hills Villa Near Disney with Heated Pool & Game Room (Kissimmee)
A dining area with a table, chairs, a television, and a ceiling fan. - Windsor Hills Villa Near Disney with Heated Pool & Game Room (Kissimmee)
A modern kitchen with stainless steel appliances, white cabinetry, and a large island with a sink. - Windsor Hills Villa Near Disney with Heated Pool & Game Room (Kissimmee)
Near Mystic Dunes Golf Club, Windsor Hills Villa Near Disney with Heated Pool & Game Room provides golfing on-site, an arcade/games room and laundry facilities. For some rest and relaxation, visit the hot tub. Stay connected with free in-room WiFi, and guests can find other amenities, such as a gym.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Add dates for prices

About this property

Windsor Hills Villa Near Disney with Heated Pool & Game Room

  • YOUR FAMILY’S DISNEY VACATION HOME IN WINDSOR HILLS RESORT

    5 Bedrooms | 5 Bathrooms | Sleeps 12 | Private Pool & Spa | Game Room

    Planning a Disney vacation with family or friends? Enjoy the comfort of your own 5-bedroom, 5-bathroom vacation villa in Windsor Hills Resort, Kissimmee, approximately 12 minutes from Walt Disney World.

    Perfect for family vacations, multigenerational trips, and group getaways, this spacious Orlando-area vacation rental sleeps up to 12 guests and offers everything you need for a memorable Florida stay.

    Enjoy your own private south-facing pool and spa, a game room with pool table, ping-pong, foosball and Xbox, two whimsical themed kids’ bedrooms, and complimentary access to Windsor Hills Resort’s water park and family-friendly amenities.

    Spend your days exploring Disney, enjoying the resort, or simply relaxing by your own pool. Here, the vacation fun doesn’t have to end when you leave the parks.

    WHY FAMILIES LOVE THIS WINDSOR HILLS VILLA

    ✓ Approximately 12 minutes to Walt Disney World
    ✓ 5 bedrooms and 5 bathrooms | Sleeps up to 12
    ✓ Private screened, south-facing pool and spa
    ✓ Game room with pool table, ping-pong, foosball and Xbox
    ✓ Two themed children’s bedrooms
    ✓ Smart TVs in every bedroom
    ✓ Fully equipped kitchen
    ✓ Spacious living and dining areas
    ✓ Outdoor dining and lounge space
    ✓ Washer and dryer
    ✓ Complimentary Wi-Fi
    ✓ Windsor Hills Resort water park and amenities
    ✓ 24-hour manned resort entrance

    Whether you’re visiting Disney World, attending an ESPN sports event, or planning a relaxing Orlando family getaway, this Windsor Hills vacation home offers the space, comfort, and entertainment to make your stay special.

    PRIVATE SOUTH-FACING POOL & SPA

    Your own Florida retreat awaits.

    After an exciting day at Walt Disney World, return to your private screened pool and spa, where the whole family can unwind without leaving the comfort of your vacation home.

    Start your morning with a refreshing swim, spend the afternoon lounging in the Florida sunshine, or enjoy a relaxing evening by the pool.

    With a south-facing pool area, outdoor seating, and space for dining, you’ll have plenty of opportunities to enjoy Florida’s beautiful weather.

    It’s the perfect setting for making memories between Disney adventures.

    5 BEDROOMS & 5 BATHROOMS — ROOM FOR EVERYONE

    Traveling with a large family or multiple generations?

    This spacious 5-bedroom Windsor Hills villa comfortably accommodates up to 12 guests, with five bathrooms to make busy mornings and relaxing evenings easier.

    Each bedroom features a Smart TV and its own bathroom, giving everyone a comfortable space to recharge.

    Primary King Suite
    King bed | Ensuite bathroom | Walk-in shower

    Coastal King Suite
    King bed | Ensuite bathroom | Walk-in shower

    Up & Away Queen Room
    Queen bed | Private bathroom | Bathtub

    Hundred Acre Wood Room
    Twin bunk beds and trundle | Winnie-the-Pooh-inspired themed bedroom

    Princess Room
    Two twin beds | Whimsical princess-themed bedroom

    The playful children’s rooms add a little extra magic to your Disney vacation, while the spacious king and queen bedrooms give adults a welcoming place to relax.

    GAME ROOM FUN FOR ALL AGES

    The fun doesn’t stop when you get home from Disney!

    Challenge your family to a friendly game of pool, ping-pong, or foosball, or settle in for some Xbox gaming.

    Whether you’re enjoying a break from the theme parks, spending a rainy afternoon indoors, or planning a relaxing day at home, the game room offers entertainment for both kids and adults.

    And when you’re ready for a swim, your private pool is just steps away.

    COMFORTABLE LIVING & FAMILY DINING

    Make yourself at home.

    The spacious living area offers a welcoming place to relax, watch a movie, or spend time together after a busy day exploring Orlando’s attractions.

    The fully equipped kitchen makes preparing family meals easy, whether you’re enjoying breakfast before heading to Disney, packing snacks for the day, or sharing dinner at home.

    You’ll also enjoy:

    • Comfortable living and dining spaces
    • Fully equipped kitchen
    • Outdoor dining and seating
    • Smart TVs in every bedroom
    • Complimentary Wi-Fi
    • Washer and dryer

    With plenty of room to gather and separate spaces to unwind, everyone can enjoy their vacation at their own pace.

    WINDSOR HILLS RESORT — WATER PARK & FAMILY AMENITIES

    Experience the best of both worlds: the privacy of your own vacation villa and the fun of staying in one of the Orlando area’s popular family-friendly resort communities.

    Located in Windsor Hills Resort, your vacation home includes access to a variety of resort amenities.

    Enjoy complimentary access to:

    ✓ Resort water park with slides
    ✓ Large community swimming pool
    ✓ Children’s splash area
    ✓ Movie theater
    ✓ Arcade
    ✓ Fitness center
    ✓ Basketball courts
    ✓ Children’s playgrounds

    Windsor Hills Resort also features a 24-hour manned entrance.

    Spend the morning exploring the water park, return home for lunch, and enjoy an afternoon swimming in your private pool.

    It’s a wonderful way to enjoy a Disney vacation with plenty of entertainment beyond the theme parks.

    CLOSE TO DISNEY WORLD & ORLANDO ATTRACTIONS

    Location matters, especially when you’re traveling with children.

    This Windsor Hills Resort vacation rental offers convenient access to Walt Disney World, ESPN Wide World of Sports, shopping, restaurants, and everyday essentials.

    Approximate driving times:

    • Walt Disney World — 12 minutes
    • ESPN Wide World of Sports — 10–12 minutes
    • Walmart — 5 minutes
    • Target — 10 minutes
    • Orlando International Airport (MCO) — 30 minutes

    Whether you’re visiting Magic Kingdom, EPCOT, Disney’s Hollywood Studios, Disney’s Animal Kingdom, or attending a sporting event at ESPN Wide World of Sports, you’ll have a comfortable home base nearby.

    Driving times may vary depending on traffic and your destination.

    MAKE YOUR DISNEY VACATION EVEN MORE MEMORABLE

    The best family vacations are about more than visiting the attractions.

    They’re about the little moments in between.

    Morning swims before Disney. Friendly competitions in the game room. Children enjoying their themed bedrooms. Family dinners after exciting park days. And relaxing evenings together by your own private pool.

    At 1 Cherry Tree Lane, you can enjoy the space and privacy of a 5-bedroom vacation home, the entertainment of a private pool and game room, and the added fun of Windsor Hills Resort’s family-friendly amenities.

    All within easy reach of Walt Disney World and Orlando’s most popular attractions.

    Ready to plan your Disney getaway?

    Check availability and book your Windsor Hills vacation home today. We look forward to welcoming you!

Similar properties

About the area

Located in Windsor Hills, a neighbourhood in Kissimmee, this holiday home is near theme parks and near a water park. Mystic Dunes Golf Club and Reunion Resort Golf Course are worth checking out if an activity is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Old Town. Travelling with kids? Don't miss Disney's Hollywood Studios® and Disney's Animal Kingdom® Theme Park. Take the opportunity to explore the area for water adventures such as swimming and other activities like golfing. Visit our Kissimmee travel guide
View more Holiday homes in Orlando
Map
Kissimmee, FL

What's nearby

  • A golf course with sand bunkers, trees, and a flagstick.
    Mystic Dunes Golf Club
    3 min drive - 1.1 miles
  • Bonanza Golf & Gifts
    3 min drive - 1.9 miles
  • Mighty Jungle Golf
    4 min drive - 2.1 miles
  • Island H2O Live!
    5 min drive - 2.4 miles
  • Orange Lake Golf
    6 min drive - 4.2 miles

Getting around

  • Kissimmee Station
    26 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    21 min drive

Restaurants

  • McDonald's
    4 min drive
  • Starbucks
    3 min drive
  • El Cafetal Bakery & Restaurant
    3 min drive
  • Del Taco
    3 min drive
  • IHOP
    3 min drive

Frequently asked questions

Does Windsor Hills Villa Near Disney with Heated Pool & Game Room have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Windsor Hills Villa Near Disney with Heated Pool & Game Room pet-friendly?

No, pets are not allowed at this property.

How much is parking at Windsor Hills Villa Near Disney with Heated Pool & Game Room?

On-site parking is available at the property.

What time is check-in at Windsor Hills Villa Near Disney with Heated Pool & Game Room?

Check-in begins at 4:00 PM.

What time is check-out at Windsor Hills Villa Near Disney with Heated Pool & Game Room?

Checkout is at 10:00 AM.

Where is Windsor Hills Villa Near Disney with Heated Pool & Game Room located?

This family-friendly Kissimmee holiday home is located in Windsor Hills, within 3 mi (5 km) of Island H2O Live! and Walt Disney World® Resort. Mystic Dunes Golf Club is 2.9 mi (4.6 km) away.

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Reviews

Windsor Hills Villa Near Disney with Heated Pool & Game Room Reviews

9.8

Exceptional

9.8

Cleanliness

10

Location
Rating 10 - Excellent. 116 out of 125 reviews
Rating 8 - Good. 7 out of 125 reviews
Rating 6 - Okay. 1 out of 125 reviews
Rating 4 - Poor. 0 out of 125 reviews
Rating 2 - Terrible. 1 out of 125 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our second stay here did not disappoint. Love this house, location and the communication provided. Hope to be back again!
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Excellent house with an excellent location very quiet we enjoyed it a lot
Stayed 5 nights in Oct 2024
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacation

A nice stay and location.
Stayed 6 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a blast. The property was very clean and was easy to check in. The parking is limited and can be a hassle if you have visitors but our host fixed the issue very quick, was polite, and was awesome. The pool was amazing but the heat was a little much during summer. The kids had a blast with the floats and game room. Kitchen was fully supplied. Neighborhood was nice. Great location if you are visiting for then parks. Walmart is always crazy busy but so close. We would come back for sure! Love it
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place-

Convenient location!
Stayed 6 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thank you Jennibelle for making our stay in Kissimmee absolutely wonderful. This property is located in the perfect spot for any Disney/Orlando area vacation. The home was perfect (minus a few minor details) which were quickly responded to and remedied above and beyond. The pool and jacuzzi on site were so nice at the end of our long days. The amenities available at the clubhouse as well as the entire staff working there are SO hospitable. You can tell they are accustomed to taking care of part-time guests. We felt welcome from the minute we drove through the entry gate. We had a memorable trip and having a comfortable, clean, roomy place to stay made it even better!
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacay

Everything was excellent, house was roomy and clean, and the neighborhood was nice. Very close to Disney and other shopping and restaurants.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Property

The house was beautiful and just like the pictures. Enjoyed being able to walk out to the pool and hot tub. Would definitely stay here again.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for a family weekend

We started for a long Labor Day and we're impressed by the community amenities and house. Plenty of space, our own pool, and access to a resort style pool. Perfect for our family gathering.
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A wonderful time!!

We had a great time and had no issues with the rental. It was so nice having all that space for our group.
Stayed 4 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Totally perfect

Everything about the property was top notch. Location was awesome for visiting Disney parks! Plenty of room for all 7 of us! Clean and nice amenities in the neighborhood! Would stay here again for sure!
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent accomodations

This is a great property. Very clean, spacious, and beautiful. The owner paid attention to details from decorations to pool toys, games, and puzzles. Our family enjoyed the private pool and hot tub. I highly recommend this property.
Stayed 5 nights in Feb 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Clean beautiful home

This house was centrally located to lots of attractions, but yet the home was quiet and peaceful! We enjoyed just staying home and relaxing in the beautiful outdoor pool and patio area.
Stayed 9 nights in Mar 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family time

The stay was just as described. We found the property in good shape and enjoyable. Our grandkids lived the heated pool. Over all a good experience.
Stayed 6 nights in Dec 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay in Kissimmee

This is property has the perfect location. My family was close to all of the attractions. The younger ones enjoyed the private pool and going to larger pool/ water park on property. There was something for everyone. I also enjoyed the amount of space the house had.
Stayed 6 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Close to Disney

The house was beautifully decorated with classy Disney decor and was a short drive from the Disney parks. We had plenty of room to spread out on our extended family stay with each of us having our own space to retreat to. The common areas were well sized for when we were all together. Our family enjoyed our stay; in fact, it was practically perfect!
Stayed 6 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing Stay

Windsor Hills is our go-to neighborhood for our Orlando stays. Jeni is a pleasure to work with. Very accessible and easy communication. We love the layout of the home with plenty of room for 5 adults. Highly recommend! We plan to book again.
Stayed 4 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Great location near all Disney parks. Lots of restaurant options nearby. Property manager was responsive on questions we had. One tip, use the shortcut through Sherberth Road to get to parks. We found it to be the quickest way to and from all the parks.
Stayed 5 nights in Jan 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect!

The property was perfect for our family! All 5 bedrooms and 5 bathrooms were clean and comfortable. The indoor space and outdoor space was well maintained and accommodating. The kids LOVED the game room! This will be our first choice when we return to the area!
Stayed 4 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Rental

We have stayed many times at Windsor Hills and the complex never disappoints. This home was particularly nice and spacious for our group of nine. Great place to relax after a long day at Disney parks, very convenient to access the parks and close to Walmart, restaurants, etc. The owner was very responsive, flexible, and just generally helpful in answering questions.
Stayed 4 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Disney with a toddler and 8 adults.

Exactly what we wanted. A nice house with 5’ bedrooms and bathrooms and pool. That would accommodate us all. And where we could all be together but with enough space to chill and relax. Also With the added benefit of being close to the parks and the Windsor hills resort pool.
Stayed 4 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing!

The house was everything we wanted and then some! The checking process was easy, especially since we arrived early. I communicated with the host and she let us get in the house early. We loved all the Disney touches throughout the house. The house was in GREAT location to the parks.We are already planning our next trip to Disney and we will be using this house again.
Stayed 7 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay, excellent location, very responsive management

Our family has stayed in this community a few times and this is the first time in this house. The proximity to the community pool was great - far enough way for privacy but close enough for a short walk. The house had everything we needed, and the layout was perfect for a big family (4 adults, including two grandparents and 3 boys). We had one or two minor issues but the manager resolved these immediately, so we were really happy with the quick resolution - we’ve stayed in other spots were issues haven’t been resolved. I’d definitely recommend a stay here and will be looking to book here again on our next trip.
Stayed 9 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Practically perfect indeed

House was as expected. Spacious for our group of 7. Outdoor patio was where we spent most of our time, however, neighbors directly behind ruined tranquility with the alarm beeping constantly on their patio door (which was out of the control of the rental home owner). Jenni the home owner responded quickly to all questions. Would definitely stay here again. Thank you Jenni!!
Stayed 7 nights in Feb 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved this VRBO

Each couple/family had their own bedroom and bathroom., which allowed a large group of people to get ready to go to the parks much easier. Loved our pool, made great use of it. Enjoyed the community pool and water slides/splashoad. Great location to get to the parks. We missed a few days of our stay due to Hurricane Milton. Will reach out to our travel insurance on that for refund. But the days we were there were wonderful. We will be back.
Stayed 7 nights in Oct 2024