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Windsor Hills Villa Near Disney with Heated Pool & Game Room

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An aerial view of a resort with multiple swimming pools, a water park, and surrounding buildings.
A dining area with a table, chairs, a television, and a ceiling fan.
A modern kitchen with stainless steel appliances, white cabinetry, and a large island with a sink.
A spacious indoor area with tiled flooring, multiple seating arrangements, ceiling fans, and large windows allowing natural light.
A living room with a large flat-screen TV, a coffee table, blue sofas, and a view of a swimming pool.

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 11223 sq m

Popular amenities

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

Explore the area

View map
Kissimmee, FL
  • Place, Mystic Dunes Golf Club
    ‪3 min drive‬
  • Place, Bonanza Golf & Gifts
    ‪3 min drive‬
  • Place, Island H2O Live!
    ‪5 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪32 min drive‬

Room options

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About the area

Kissimmee

A family-friendly stay in Kissimmee awaits you at this holiday home. You'll be 4.6 km (2.8 mi) from Walt Disney World® Resort and 4.1 km (2.5 mi) from Island H2O Live!. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 5 bathrooms and a balcony or patio. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a dining area and a Smart TV are also available. .Enjoy the outdoor swimming pool, gym and Hot tub. Added amenities include free Wi-Fi in public areas and laundry facilities. .Attractions within a 10-minute drive of this Windsor Hills holiday home include Old Town and Mystic Dunes Golf Club.

What's nearby

  • Mystic Dunes Golf Club - 3 min drive - 1.7 km
  • Bonanza Golf & Gifts - 3 min drive - 3.0 km
  • Mighty Jungle Golf - 4 min drive - 3.4 km
  • Island H2O Live! - 5 min drive - 3.8 km
  • Orange Lake Golf - 6 min drive - 6.8 km

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car required
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 5 private bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Games
  • Smart TV with cable/satellite channels
  • Video games

Outdoor areas

  • Barbecue grill
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • No lift
  • Smoke-free property
  • Note from host: Includes Vaping and is Grounds for Eviction

Services and conveniences

  • Concierge services
  • Iron/ironing board
  • Phone

Location highlights

  • Near a hospital

Things to do

  • Arcade/game room
  • Billiards/pool table
  • Foosball table
  • Golf
  • Gym
  • Heated pool
  • Table tennis
  • Tennis
  • Basketball nearby
  • Golfing nearby
  • Swimming nearby
  • Theme park nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Gated community
  • Property located in a resort
  • Unit size: 2,400 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed
Please Inquire

Smoking

Smoking is not permitted
Includes Vaping and is Grounds for Eviction

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: Please Inquire
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. Note from host: Please Inquire For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a deadbolt lock in all accommodation.

Property is also known as

Delightfully Through Through
Delightfully New Through Through
***Delightfully New*** Through Through
NEW Listing 5br/5ba Windsor Hills Resort Home
***Delightfully New*** Through and Through Kissimmee
***Delightfully New*** Through and Through Private vacation home

Frequently asked questions

Are there any beaches close to Windsor Hills Villa Near Disney with Heated Pool & Game Room?

The closest beach to Windsor Hills Villa Near Disney with Heated Pool & Game Room is Hideaway Bay (8.3 km).

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

Take your pick from a heated pool, a pool and a communal pool.

What luxury perks are available at Windsor Hills Villa Near Disney with Heated Pool & Game Room?

This property features a heated pool, as well as a private pool and a living room.

What makes Windsor Hills Villa Near Disney with Heated Pool & Game Room a romantic place to stay?

1 hot tub, private pools, and private balconies all help set the scene for a sizzling getaway at Windsor Hills Villa Near Disney with Heated Pool & Game Room.

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

You bet! With amenities such as an arcade, laundry facilities and travel cots, it's no surprise that Windsor Hills Villa Near Disney with Heated Pool & Game Room is a winner with our family travellers.

Is there a private hot tub at Windsor Hills Villa Near Disney with Heated Pool & Game Room?

Yep, there is a hot tub.

Is there a free airport shuttle available at Windsor Hills Villa Near Disney with Heated Pool & Game Room?

No, Windsor Hills Villa Near Disney with Heated Pool & Game Room does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Windsor Hills Villa Near Disney with Heated Pool & Game Room?

No, pets are not allowed.

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

Reviews

9.8

Exceptional

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

9.8/10

Cleanliness

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a pleasant stay!
Stayed 7 nights in Dec 2025
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

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay. It was the perfect property for 2 families to share.Our only issue was the security gate using rideshares. We would have to wait in line for up to 45 minutes just to be let in. In one case, the security staff asked for our driver's permit and more, which seemed unnecessary and an overstep.
Stayed 8 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had the best time during our stay. The house was beautiful. Jenni was very helpful and so responsive to any issues. I would recommend this home to anyone visiting the area.
Stayed 9 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great open floor plan the home feels cozy and home with a little or enough Disney cute flair. Backyard pool and hot tub was enough space for all to enjoy. This house thought of everything!! Was very very impressed.
Stayed 5 nights in Apr 2026
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

Awesome Stay! Great home!

Great home! Everyone enjoyed the stay! If we are in this area again, we would choose to stay here if available.
Stayed 5 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay at this property. The hostess was very accommodating and the house was well stocked with cookware and appliances. The house was very clean on arrival and we enjoyed the heated pool and hot tub. The property is close to all amenities and close to Disney.
Stayed 8 nights in Nov 2025
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

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
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

Beautiful house

I would definitely stay there again. Loved the Disney decor on the walls.
Stayed 13 nights in Feb 2023
Verified review

10/10 Excellent

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

Perfect stay

We loved everything about this stay. Communication was quick and easy, the listing was very accurate. The neighborhood and waterpark was the best part. We would highly recommend this property!
Stayed 4 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

Our stay was great and the house did not disappoint.

The house was amazing and very clean. great location and we were very happy
Stayed 5 nights in Feb 2023
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

Excellent

Thank you, home was as advertised. Had a wonderful vacation. Would stay again.
Stayed 8 nights in Mar 2024
Verified review

10/10 Excellent

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

Magical

Thank you for making our 2nd stay in your magical. We had an amazing time!
Stayed 6 nights in Sep 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

April Vacation

The house was beautiful! It is close to the Disney Parks so dropping off my adult children and driving back to the house with my elderly dad was easy. I would s]tay again at this beautiful home.
Stayed 8 nights in Apr 2023
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