House in Windsor Hills, FL
11 guests · 5 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
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About this house rental
Windsor Hills 5BR Near Disney | Private Pool & Spa | Game Room | Sleeps 12
YOUR PRIVATE FAMILY RETREAT NEAR DISNEY
Make your Disney vacation even better with the space and privacy of your own 5-bedroom, 5-bathroom vacation home in Windsor Hills Resort, approximately 12 minutes from Walt Disney World.
Sleeping up to 12 guests, this family-friendly Kissimmee villa has something for everyone: a private south-facing pool & spa, a game room with pool table, ping-pong, foosball and Xbox, two themed kids’ bedrooms, Smart TVs in every bedroom, and complimentary access to the Windsor Hills Resort water park and amenities.
Spend exciting days at Disney, cool off in your own pool, challenge the family in the game room, and end the evening with plenty of space for everyone to relax.
WHY FAMILIES LOVE THIS WINDSOR HILLS HOME
✓ Approx. 12 minutes to Walt Disney World
✓ 5 bedrooms | 5 bathrooms | Sleeps 12
✓ Private south-facing pool & spa
✓ Pool, ping-pong, foosball & Xbox
✓ Two themed kids’ bedrooms
✓ Smart TV in every bedroom
✓ Fully equipped kitchen
✓ Outdoor dining & lounge area
✓ Washer & dryer
✓ Free Wi-Fi
✓ Windsor Hills water park & resort amenities
✓ 24-hour manned resort entrance
YOUR OWN PRIVATE POOL & SPA
Some of the best vacation moments happen after you leave the parks.
Come home from Disney and step outside to your private screened, south-facing pool and spa. Swim with the kids, relax in the spa, enjoy the Florida sunshine or settle in for an easy evening together without leaving the villa.
The outdoor area also includes space for dining and lounging, giving your family another place to enjoy the Florida weather.
ROOM FOR THE WHOLE FAMILY — 5 BEDROOMS & 5 BATHROOMS
No fighting over bathrooms in the morning.
With five bedrooms and five bathrooms, your group can spread out, get ready for the parks and unwind comfortably at the end of the day.
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 | Tub
Hundred Acre Wood Room
Twin bunk beds + trundle | Playful themed bedroom
Princess Room
Two twin beds | Whimsical themed bedroom
Each bedroom has its own Smart TV and bathroom, giving families and groups more privacy throughout their stay.
A GAME ROOM THEY’LL ACTUALLY USE
Need a break from the theme parks?
Stay home and start a family tournament.
Play pool, ping-pong or foosball, enjoy some Xbox time, or head straight from the game room to the pool for an afternoon at the villa.
It’s an easy way to keep both kids and adults entertained on slower vacation days, rainy afternoons or evenings after Disney.
SPACE TO EAT, RELAX & SPEND TIME TOGETHER
Vacationing together doesn’t mean everyone has to be crowded into one room.
The open living space gives your group somewhere comfortable to relax after long park days, while the fully equipped kitchen makes everything from quick breakfasts before Disney to family dinners at home easier.
The kitchen overlooks the pool area, helping everyone stay connected whether they’re inside preparing food or outside enjoying the pool.
A washer and dryer are also available in the home — especially convenient for longer stays and families traveling with children.
WINDSOR HILLS RESORT AMENITIES — INCLUDED WITH YOUR STAY
When you want even more to do, head out and enjoy the family-friendly amenities at Windsor Hills Resort.
Your stay includes access to:
• Water park with slides
• Large community swimming pool
• Movie theater
• Arcade
• Fitness center
• Basketball courts
• Children’s playgrounds
The resort also has a 24-hour manned entrance.
So you can enjoy the privacy of your own pool and vacation home while still having resort-style entertainment nearby.
STAY CLOSE TO DISNEY
Less time getting there. More time enjoying your vacation.
From your Windsor Hills home, you’ll be conveniently located near Disney, ESPN Wide World of Sports, shopping and everyday essentials.
Walt Disney World — approx. 12 minutes
ESPN Wide World of Sports — approx. 10–12 minutes
Walmart — approx. 5 minutes
Target — approx. 10 minutes
Orlando International Airport (MCO) — approx. 30 minutes
Whether your plans include early mornings at Disney, an ESPN sports event, relaxing pool days or a little of everything, you’ll have a convenient home base to return to.
MORE THAN A PLACE TO SLEEP
A great Disney vacation isn’t only about the hours you spend inside the parks.
It’s morning swims before the day begins. Kids choosing between the game room and the pool. Everyone having their own space to get ready. And coming home after a long Disney day knowing you can simply relax.
At 1 Cherry Tree Lane, your family gets the space of a 5-bedroom home, the fun of a private pool and game room, the amenities of Windsor Hills Resort, and Walt Disney World approximately 12 minutes away.
Book your Windsor Hills stay and give the whole family something to look forward to, both inside and outside the parks.
YOUR PRIVATE FAMILY RETREAT NEAR DISNEY
Make your Disney vacation even better with the space and privacy of your own 5-bedroom, 5-bathroom vacation home in Windsor Hills Resort, approximately 12 minutes from Walt Disney World.
Sleeping up to 12 guests, this family-friendly Kissimmee villa has something for everyone: a private south-facing pool & spa, a game room with pool table, ping-pong, foosball and Xbox, two themed kids’ bedrooms, Smart TVs in every bedroom, and complimentary access to the Windsor Hills Resort water park and amenities.
Spend exciting days at Disney, cool off in your own pool, challenge the family in the game room, and end the evening with plenty of space for everyone to relax.
WHY FAMILIES LOVE THIS WINDSOR HILLS HOME
✓ Approx. 12 minutes to Walt Disney World
✓ 5 bedrooms | 5 bathrooms | Sleeps 12
✓ Private south-facing pool & spa
✓ Pool, ping-pong, foosball & Xbox
✓ Two themed kids’ bedrooms
✓ Smart TV in every bedroom
✓ Fully equipped kitchen
✓ Outdoor dining & lounge area
✓ Washer & dryer
✓ Free Wi-Fi
✓ Windsor Hills water park & resort amenities
✓ 24-hour manned resort entrance
YOUR OWN PRIVATE POOL & SPA
Some of the best vacation moments happen after you leave the parks.
Come home from Disney and step outside to your private screened, south-facing pool and spa. Swim with the kids, relax in the spa, enjoy the Florida sunshine or settle in for an easy evening together without leaving the villa.
The outdoor area also includes space for dining and lounging, giving your family another place to enjoy the Florida weather.
ROOM FOR THE WHOLE FAMILY — 5 BEDROOMS & 5 BATHROOMS
No fighting over bathrooms in the morning.
With five bedrooms and five bathrooms, your group can spread out, get ready for the parks and unwind comfortably at the end of the day.
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 | Tub
Hundred Acre Wood Room
Twin bunk beds + trundle | Playful themed bedroom
Princess Room
Two twin beds | Whimsical themed bedroom
Each bedroom has its own Smart TV and bathroom, giving families and groups more privacy throughout their stay.
A GAME ROOM THEY’LL ACTUALLY USE
Need a break from the theme parks?
Stay home and start a family tournament.
Play pool, ping-pong or foosball, enjoy some Xbox time, or head straight from the game room to the pool for an afternoon at the villa.
It’s an easy way to keep both kids and adults entertained on slower vacation days, rainy afternoons or evenings after Disney.
SPACE TO EAT, RELAX & SPEND TIME TOGETHER
Vacationing together doesn’t mean everyone has to be crowded into one room.
The open living space gives your group somewhere comfortable to relax after long park days, while the fully equipped kitchen makes everything from quick breakfasts before Disney to family dinners at home easier.
The kitchen overlooks the pool area, helping everyone stay connected whether they’re inside preparing food or outside enjoying the pool.
A washer and dryer are also available in the home — especially convenient for longer stays and families traveling with children.
WINDSOR HILLS RESORT AMENITIES — INCLUDED WITH YOUR STAY
When you want even more to do, head out and enjoy the family-friendly amenities at Windsor Hills Resort.
Your stay includes access to:
• Water park with slides
• Large community swimming pool
• Movie theater
• Arcade
• Fitness center
• Basketball courts
• Children’s playgrounds
The resort also has a 24-hour manned entrance.
So you can enjoy the privacy of your own pool and vacation home while still having resort-style entertainment nearby.
STAY CLOSE TO DISNEY
Less time getting there. More time enjoying your vacation.
From your Windsor Hills home, you’ll be conveniently located near Disney, ESPN Wide World of Sports, shopping and everyday essentials.
Walt Disney World — approx. 12 minutes
ESPN Wide World of Sports — approx. 10–12 minutes
Walmart — approx. 5 minutes
Target — approx. 10 minutes
Orlando International Airport (MCO) — approx. 30 minutes
Whether your plans include early mornings at Disney, an ESPN sports event, relaxing pool days or a little of everything, you’ll have a convenient home base to return to.
MORE THAN A PLACE TO SLEEP
A great Disney vacation isn’t only about the hours you spend inside the parks.
It’s morning swims before the day begins. Kids choosing between the game room and the pool. Everyone having their own space to get ready. And coming home after a long Disney day knowing you can simply relax.
At 1 Cherry Tree Lane, your family gets the space of a 5-bedroom home, the fun of a private pool and game room, the amenities of Windsor Hills Resort, and Walt Disney World approximately 12 minutes away.
Book your Windsor Hills stay and give the whole family something to look forward to, both inside and outside the parks.
Amenities at Windsor Hills 5BR Near Disney | Private Pool & Spa | Game Room | Sleeps 12
Non-smoking
No pets allowed
Family friendly
Map of Windsor Hills, FL
Ratings and reviews
10 / 10Outstanding·Jun 2026
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!
10 / 10Outstanding·May 2026
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.
10 / 10Outstanding·Mar 2026
Our second stay here did not disappoint. Love this house, location and the communication provided. Hope to be back again!
6 / 10Average·Feb 2025
A nice stay and location.
$$$$
Top rated by guests
9.9Outstanding
(123 Ratings)
"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..."
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