Entire home

Disney Villa | Private Pool & Spa | Cinema | Arcade | 12 Guests | Windsor Hills

Photo gallery for Disney Villa | Private Pool & Spa | Cinema | Arcade | 12 Guests | Windsor Hills

Outdoor pool, a heated pool - Disney Villa | Private Pool & Spa | Cinema | Arcade | 12 Guests | Windsor Hills (Kissimmee)
Outdoor dining - Disney Villa | Private Pool & Spa | Cinema | Arcade | 12 Guests | Windsor Hills (Kissimmee)
Dining - Disney Villa | Private Pool & Spa | Cinema | Arcade | 12 Guests | Windsor Hills (Kissimmee)
Fridge, microwave, oven, stovetop - Disney Villa | Private Pool & Spa | Cinema | Arcade | 12 Guests | Windsor Hills (Kissimmee)
Smart TV, video games, table football, ping pong - Disney Villa | Private Pool & Spa | Cinema | Arcade | 12 Guests | Windsor Hills (Kissimmee)
Windsor Hills Resort Home, located just three miles from Disney's Main Gate, offers a luxurious retreat with a private pool and spa. Unwind in the Southwest-facing sun deck or enjoy activities like billiards, Foosball, or watching movies in the theater. With comfortable features like climate-controlled garage gaming and high-speed WiFi throughout your stay will be enjoyable.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 11223 sq m

Popular amenities

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

Add dates for prices

About this property

Entire place

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

Disney Villa | Private Pool & Spa | Cinema | Arcade | 12 Guests | Windsor Hills

🏰 12 MINUTES TO WALT DISNEY WORLD · WINDSOR HILLS RESORT · ORLANDO, FLORIDA

Imagine this: It's early morning in Orlando. Your kids are still dreaming — one tucked under Winnie-the-Pooh murals, another asleep in a princess-pink room, while you stand in the kitchen with your coffee, watching the Florida sun rise over your private south-facing heated pool. Steam curls off the spa. The gate is manned 24 hours. And in twelve minutes, you'll be at Walt Disney World.

Tonight you'll be back here, in your private cinema, at the arcade, around one of two pool tables, or floating in that spa under the stars.

Welcome to 1 Cherry Tree Lane. The Disney vacation home your family will never stop talking about.
📍 LOCATION — KISSIMMEE / ORLANDO, FL
🏰 Walt Disney World — 12 minutes
🏨 World Center Drive, Orlando — 17 minutes
✈️ Orlando International Airport — ~30 minutes
⛳ Golf course — nearby
🛒 Walmart — 5 min · Target — 10 min.
🏠 THE HOME

This 5-bedroom, 5-bathroom English cottage–inspired retreat sleeps up to 12 guests inside Windsor Hills Resort, one of Orlando's most sought-after, 24-hour manned gated communities. From the sweeping two-story foyer to the thoughtfully themed bedrooms, every inch was prepared for families who want magic beyond the parks.
🛏️ BEDROOMS — Every Child Becomes the Main Character
🌿 Primary King Retreat — garden-inspired Disney suite, walk-in shower ensuite
🌊 Coastal King Room — serene blue king bedroom, walk-in shower ensuite
🎈 Up & Away Room — Pixar-inspired queen room, bathtub ensuite
🍯 Hundred Acre Wood Room — Pooh-themed twin bunks + trundle, bathtub ensuite
👑 Princess Room — blush pink twin room, bathtub ensuite
Every room: Smart TV · Ensuite bathroom · Hotel-quality linens
🏊 PRIVATE SOUTH-FACING HEATED POOL & SPA

Your private pool and spa are heated 24 hours a day, year-round. South-facing means maximum Florida sunshine from morning to sundown. A pool fence keeps little ones safe. Pool towels are provided. Late-night swims are not just allowed — they're encouraged.
🎬 PRIVATE CINEMA
Perfect for rainy afternoons, post-park wind-downs, or late-night family film nights. No queues. No strangers. Just your family and the screen.
🎱 ULTIMATE GAME ROOM
Pool table
Arcade games
Three Xbox consoles
Table tennis
ATM machine on-site.
🏘️ WINDSOR HILLS RESORT COMMUNITY AMENITIES
24-hour manned gated security
Resort-style community pool
Basketball courts
Tennis courts
Playgrounds · BBQ areas · Golf nearby
👶 FAMILY & GROUP ESSENTIALS
High chair · Pack-n-play · Stroller · Pool fence · Optional stair gates
Fully equipped kitchen · Dining for 8
Bath towels + pool towels provided
✦ PERFECT FOR: Disney families · Multi-generational trips · Group vacations · Large family reunions · Couples travelling together · Anyone who wants a luxury Orlando vacation home with the space to breathe.

At Practically Perfect Properties, we believe where you stay shapes how you remember your trip. Every detail at 1 Cherry Tree Lane was chosen to give your family something the parks cannot: a home to come back to.

Your Disney story deserves the perfect first chapter. This is it.

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

Similar properties

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

Pets not 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

We should mention

This property does not have any lifts
A car is required for transport to and from this property

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 Blizzard Beach Water 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

  • Mystic Dunes Golf Club
    Mystic Dunes Golf Club
    2 min drive - 1.4 km
  • www.alamy.com
    Walt Disney World® Resort
    6 min drive - 4.7 km
  • Bonanza Golf & Gifts
    3 min drive - 2.7 km
  • Mighty Jungle Golf
    3 min drive - 3.1 km
  • Island H2O Live!
    4 min drive - 3.4 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
  • Del Taco
    3 min drive
  • Osaka Bay Buffet
    3 min drive
  • Sickies Garage Burgers & Brews
    4 min drive

Frequently asked questions

Does Family Retreat w/ Heated Pool • Hot tub • Game RM •Near Disney & 10 Mins to ESPN have a pool?

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

Is Family Retreat w/ Heated Pool • Hot tub • Game RM •Near Disney & 10 Mins to ESPN pet-friendly?

No, pets are not allowed at this property.

How much is parking at Family Retreat w/ Heated Pool • Hot tub • Game RM •Near Disney & 10 Mins to ESPN?

On-site parking is available at the property.

What time is check-in at Family Retreat w/ Heated Pool • Hot tub • Game RM •Near Disney & 10 Mins to ESPN?

Check-in begins at 4:00 PM.

What time is check-out at Family Retreat w/ Heated Pool • Hot tub • Game RM •Near Disney & 10 Mins to ESPN?

Checkout is at 10:00 AM.

Where is Family Retreat w/ Heated Pool • Hot tub • Game RM •Near Disney & 10 Mins to ESPN 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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Disney Villa | Private Pool & Spa | Cinema | Arcade | 12 Guests | Windsor Hills Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 108 out of 116 reviews
Rating 8 - Good. 7 out of 116 reviews
Rating 6 - Okay. 1 out of 116 reviews
Rating 4 - Poor. 0 out of 116 reviews
Rating 2 - Terrible. 0 out of 116 reviews

10

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

Rodrigo Vallejo R.

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

6/10 Okay

rich d.

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

Vacation

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

10/10 Excellent

Dominic B.

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

Nice place-

Convenient location!
Stayed 6 nights in Jan 2025
Verified

10/10 Excellent

Michael M.

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

10/10 Excellent

Susan S.

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

10/10 Excellent

Ashley M.

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

10/10 Excellent

Kellie W.

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

8/10 Good

Terri B.

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

10/10 Excellent

Heather H.

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

10/10 Excellent

Joy J.

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

10/10 Excellent

Kymberly R.

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

8/10 Good

Nikkitoyya I.

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

10/10 Excellent

Jen M.

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

10/10 Excellent

Amber P.

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

10/10 Excellent

Jason G.

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

10/10 Excellent

Howard B.

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

10/10 Excellent

Steven E.

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

10/10 Excellent

Jessica B.

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

10/10 Excellent

jan W.

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

10/10 Excellent

Stephanie K.

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

10/10 Excellent

Andrew O.

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

10/10 Excellent

Ashley L.

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

Perfect stay

What a wonderful spot! The house is huge, clean, and the perfect location for Disney. We had 4 adults and 7 kids and there was plenty of space. The host was extremely kind and provided us 2 pack and plays for the babies. The kids loved the game room. The pool at the house was warm and a great time. The netting around the pool gave us peace of mind. Less than 15 minutes to Disney. Walmart within 4 mins. The waterpark at the resort was an absolute highlight with slides, a movie theatre and lots of kids activities. We will absolutely be coming back! Truly couldn’t have had a better time. Thank you host!!!
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Shannon P.

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
Verified

10/10 Excellent

Bethany J.

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

Perfect stay!

My family and I had such an amazing stay! The check in process was easy and smooth. The host was very responsive when we had questions! Couldn’t have asked for a better place to stay. The house was so clean and organized. If I had to make any critiques it would be there are no games for the Xbox. Not a big deal as there was plenty to do otherwise. The community pool and water slides were within a 3 minute walk. The house is centrally location to many Orlando attractions! The farthest one was Legoland and still within 45 mins. We will definitely be staying again!
Stayed 5 nights in Feb 2025
Verified

10/10 Excellent

D S.

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

Our GREAT, hot, hot, hot vacation!

We had a blast at Jolly Delight. Couldn’t get the girls out of the pool even to go to Disney World. We were fortunate to be able to hike through Disney on record heat days, probably lost 5 lbs each! Still a once in a lifetime trip experiencing the world through 5 and 7 year old eyes again. Great managers. Only wishes - a 9x13 casserole dish for family dinners and a heads up before hand on the ice situation.
Stayed 7 nights in Jun 2024