House in Windsor Hills, FL
11 guests · 5 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
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About this house rental
SPEND CHRISTMAS NEAR DISNEY WORLD AT WINDSOR HILLS RESORT
5 Bedrooms | 5 Bathrooms | Sleeps 12 | Private Pool & Spa | Game Room
Make Christmas 2026 extra magical with a family getaway near Walt Disney World!
Located in Windsor Hills Resort in Kissimmee, approximately 12 minutes from Disney World, this spacious 5-bedroom, 5-bathroom vacation villa offers the perfect home base for celebrating the holidays with family and friends.
Whether you’re planning a Christmas vacation at Disney, a multigenerational family gathering, or a festive Florida getaway, you’ll have plenty of space to relax, reconnect, and make holiday memories together.
Spend your mornings exploring Disney’s holiday celebrations, your afternoons enjoying your private south-facing pool and spa, and your evenings challenging the family in the game room.
Plus, enjoy complimentary access to Windsor Hills Resort’s water park and family-friendly amenities.
This Christmas, enjoy the magic of Disney and the comfort of having your own vacation home.
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 whimsical Disney-inspired children’s bedrooms
✓ Smart TVs in every bedroom
✓ Fully equipped kitchen for family meals
✓ 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 for Christmas, attending an ESPN sporting event, or escaping to Florida for a winter family vacation, this Windsor Hills villa offers everything you need for a memorable stay.
YOUR PRIVATE SOUTH-FACING POOL & SPA
Trade the winter chill for Florida sunshine!
After a magical day exploring Disney’s holiday attractions, return to your private screened pool and spa for some well-deserved relaxation.
Start your morning with a refreshing swim, spend the afternoon lounging by the pool, or unwind with the family after a full day of adventures.
The south-facing pool area features outdoor seating and dining space, making it a wonderful place to enjoy Florida’s pleasant winter weather.
Whether you’re celebrating Christmas in the sunshine or simply enjoying a relaxing family getaway, your private pool offers the perfect escape from the busy theme parks.
Pool heating is available
5 BEDROOMS & 5 BATHROOMS — SPACE FOR THE WHOLE FAMILY
Christmas is even better when everyone can celebrate together!
With five bedrooms, five bathrooms, and accommodations for up to 12 guests, this spacious villa is ideal for extended families, grandparents traveling with grandchildren, and groups celebrating the holidays together.
Each bedroom features a Smart TV, giving everyone a comfortable space to unwind after a day of Disney adventures.
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
Children will love the playful themed bedrooms, while adults can enjoy the comfort and privacy of the spacious king and queen rooms.
With room for everyone, your family can spend Christmas together without sacrificing personal space.
GAME ROOM FUN FOR EVERY GENERATION
Who says the fun has to end when you leave Disney?
Keep the holiday excitement going in your private game room, featuring:
✓ Pool table
✓ Ping-pong
✓ Foosball
✓ Xbox gaming
Challenge the family to a friendly competition, enjoy an afternoon indoors, or spend a relaxing evening playing games together.
It’s a great way to entertain everyone between theme park visits, especially when you’re traveling with children and teenagers.
And when you’re ready to cool off, your private pool is waiting!
COMFORTABLE LIVING & FAMILY DINING
Make yourself at home this Christmas.
The spacious living area provides a welcoming place for family movie nights, holiday conversations, and relaxing evenings after exploring Orlando.
The fully equipped kitchen makes it easy to prepare your favorite meals, whether you’re enjoying breakfast before heading to Disney, preparing a family dinner, or sharing a special Christmas meal together.
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
Whether you’re gathering around the table or enjoying a quiet moment by the pool, there’s plenty of room to make yourself comfortable.
WINDSOR HILLS RESORT — WATER PARK & FAMILY FUN
Enjoy the privacy of your own vacation home with the added excitement of staying in Windsor Hills Resort.
Your stay includes complimentary access to the resort’s family-friendly amenities, including:
✓ Resort water park with slides
✓ Large community swimming pool
✓ Children’s splash area
✓ Movie theater
✓ Fitness center
✓ Basketball courts
✓ Children’s playgrounds
Windsor Hills Resort also features a 24-hour manned entrance for added peace of mind.
Spend a morning at the water park, enjoy lunch at your villa, and relax by your private pool in the afternoon.
With so many activities available, your family can enjoy a wonderful Florida Christmas vacation without spending every day at the theme parks.
Resort amenity availability and operating hours may vary during the holidays.
JUST MINUTES FROM DISNEY WORLD & ORLANDO ATTRACTIONS
Make the most of your Christmas vacation with a convenient location near Orlando’s most popular attractions.
Situated in Windsor Hills Resort, this Kissimmee vacation home offers easy access to Walt Disney World, ESPN Wide World of Sports, restaurants, shopping, 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
Experience the holiday magic at Magic Kingdom, EPCOT, Disney’s Hollywood Studios, and Disney’s Animal Kingdom, then return to your comfortable home away from home.
With Disney just a short drive away, you can enjoy the excitement of the parks while having your own peaceful space to recharge.
Driving times may vary depending on traffic and your destination, particularly during the busy Christmas season.
MAKE CHRISTMAS 2026 A FAMILY VACATION TO REMEMBER
Imagine waking up on Christmas morning in your own spacious Florida vacation home.
Enjoy breakfast together before heading out to experience the magic of Disney during the holidays.
Spend sunny afternoons by your private pool, challenge the family to a game of ping-pong, and end your evenings sharing stories from another unforgettable day.
At 1 Cherry Tree Lane, you’ll enjoy:
✓ The comfort and privacy of a 5-bedroom vacation villa
✓ Your own private pool and spa
✓ Entertainment for children and adults
✓ Access to Windsor Hills Resort’s water park and amenities
✓ A convenient location approximately 12 minutes from Disney World
Whether you’re celebrating Christmas, planning a December family reunion, or simply enjoying a winter escape to Orlando, this villa is ready to be your family’s home away from home.
Planning your Christmas 2026 Disney vacation?
Check availability for your preferred December dates and book your Windsor Hills getaway.
We look forward to welcoming you and your family for a memorable holiday stay!
5 Bedrooms | 5 Bathrooms | Sleeps 12 | Private Pool & Spa | Game Room
Make Christmas 2026 extra magical with a family getaway near Walt Disney World!
Located in Windsor Hills Resort in Kissimmee, approximately 12 minutes from Disney World, this spacious 5-bedroom, 5-bathroom vacation villa offers the perfect home base for celebrating the holidays with family and friends.
Whether you’re planning a Christmas vacation at Disney, a multigenerational family gathering, or a festive Florida getaway, you’ll have plenty of space to relax, reconnect, and make holiday memories together.
Spend your mornings exploring Disney’s holiday celebrations, your afternoons enjoying your private south-facing pool and spa, and your evenings challenging the family in the game room.
Plus, enjoy complimentary access to Windsor Hills Resort’s water park and family-friendly amenities.
This Christmas, enjoy the magic of Disney and the comfort of having your own vacation home.
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 whimsical Disney-inspired children’s bedrooms
✓ Smart TVs in every bedroom
✓ Fully equipped kitchen for family meals
✓ 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 for Christmas, attending an ESPN sporting event, or escaping to Florida for a winter family vacation, this Windsor Hills villa offers everything you need for a memorable stay.
YOUR PRIVATE SOUTH-FACING POOL & SPA
Trade the winter chill for Florida sunshine!
After a magical day exploring Disney’s holiday attractions, return to your private screened pool and spa for some well-deserved relaxation.
Start your morning with a refreshing swim, spend the afternoon lounging by the pool, or unwind with the family after a full day of adventures.
The south-facing pool area features outdoor seating and dining space, making it a wonderful place to enjoy Florida’s pleasant winter weather.
Whether you’re celebrating Christmas in the sunshine or simply enjoying a relaxing family getaway, your private pool offers the perfect escape from the busy theme parks.
Pool heating is available
5 BEDROOMS & 5 BATHROOMS — SPACE FOR THE WHOLE FAMILY
Christmas is even better when everyone can celebrate together!
With five bedrooms, five bathrooms, and accommodations for up to 12 guests, this spacious villa is ideal for extended families, grandparents traveling with grandchildren, and groups celebrating the holidays together.
Each bedroom features a Smart TV, giving everyone a comfortable space to unwind after a day of Disney adventures.
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
Children will love the playful themed bedrooms, while adults can enjoy the comfort and privacy of the spacious king and queen rooms.
With room for everyone, your family can spend Christmas together without sacrificing personal space.
GAME ROOM FUN FOR EVERY GENERATION
Who says the fun has to end when you leave Disney?
Keep the holiday excitement going in your private game room, featuring:
✓ Pool table
✓ Ping-pong
✓ Foosball
✓ Xbox gaming
Challenge the family to a friendly competition, enjoy an afternoon indoors, or spend a relaxing evening playing games together.
It’s a great way to entertain everyone between theme park visits, especially when you’re traveling with children and teenagers.
And when you’re ready to cool off, your private pool is waiting!
COMFORTABLE LIVING & FAMILY DINING
Make yourself at home this Christmas.
The spacious living area provides a welcoming place for family movie nights, holiday conversations, and relaxing evenings after exploring Orlando.
The fully equipped kitchen makes it easy to prepare your favorite meals, whether you’re enjoying breakfast before heading to Disney, preparing a family dinner, or sharing a special Christmas meal together.
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
Whether you’re gathering around the table or enjoying a quiet moment by the pool, there’s plenty of room to make yourself comfortable.
WINDSOR HILLS RESORT — WATER PARK & FAMILY FUN
Enjoy the privacy of your own vacation home with the added excitement of staying in Windsor Hills Resort.
Your stay includes complimentary access to the resort’s family-friendly amenities, including:
✓ Resort water park with slides
✓ Large community swimming pool
✓ Children’s splash area
✓ Movie theater
✓ Fitness center
✓ Basketball courts
✓ Children’s playgrounds
Windsor Hills Resort also features a 24-hour manned entrance for added peace of mind.
Spend a morning at the water park, enjoy lunch at your villa, and relax by your private pool in the afternoon.
With so many activities available, your family can enjoy a wonderful Florida Christmas vacation without spending every day at the theme parks.
Resort amenity availability and operating hours may vary during the holidays.
JUST MINUTES FROM DISNEY WORLD & ORLANDO ATTRACTIONS
Make the most of your Christmas vacation with a convenient location near Orlando’s most popular attractions.
Situated in Windsor Hills Resort, this Kissimmee vacation home offers easy access to Walt Disney World, ESPN Wide World of Sports, restaurants, shopping, 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
Experience the holiday magic at Magic Kingdom, EPCOT, Disney’s Hollywood Studios, and Disney’s Animal Kingdom, then return to your comfortable home away from home.
With Disney just a short drive away, you can enjoy the excitement of the parks while having your own peaceful space to recharge.
Driving times may vary depending on traffic and your destination, particularly during the busy Christmas season.
MAKE CHRISTMAS 2026 A FAMILY VACATION TO REMEMBER
Imagine waking up on Christmas morning in your own spacious Florida vacation home.
Enjoy breakfast together before heading out to experience the magic of Disney during the holidays.
Spend sunny afternoons by your private pool, challenge the family to a game of ping-pong, and end your evenings sharing stories from another unforgettable day.
At 1 Cherry Tree Lane, you’ll enjoy:
✓ The comfort and privacy of a 5-bedroom vacation villa
✓ Your own private pool and spa
✓ Entertainment for children and adults
✓ Access to Windsor Hills Resort’s water park and amenities
✓ A convenient location approximately 12 minutes from Disney World
Whether you’re celebrating Christmas, planning a December family reunion, or simply enjoying a winter escape to Orlando, this villa is ready to be your family’s home away from home.
Planning your Christmas 2026 Disney vacation?
Check availability for your preferred December dates and book your Windsor Hills getaway.
We look forward to welcoming you and your family for a memorable holiday stay!
Amenities
Free WiFi/internet
Free Parking
Air conditioning
Pool
Non-smoking
Gym
TV
Heating
Refrigerator
Kitchen
WiFi/Internet
Hot tub/Jacuzzi
Parking Available
Private pool access
Microwave
Dishwasher
Washing machine
Dryer
Washer/dryer
Patio
Kitchenware
No pets allowed
Kettle
Oven
Stove
Laundry services
Bath or shower
Outdoor Cooking
Family friendly
Cribs or cots available
Ironing facilities
Towels
Linens
Dining table
Hairdryer
Fire extinguisher
Tennis court
Map of Windsor Hills, FL
Ratings and reviews
10 / 10Outstanding·Jul 2026
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.
10 / 10Outstanding·Jul 2026
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
10 / 10Outstanding·Jul 2026
Really nice place, very clean. Host was in constant contact as necessary. Private pool and hot tub were a great amenity. Really enjoyed our stay.
6 / 10Average·Feb 2025
A nice stay and location.
$$$$
Top rated by guests
9.9Outstanding
(123 Ratings)
"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 o..."
Jessica M.Don't miss out! Price and availability may change
