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Family Retreat w/ Heated Pool • Hot tub • Game RM •Near Disney & 10 Mins to ESPN

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Outdoor pool, a heated pool
Outdoor dining
Fridge, microwave, oven, stovetop
Smart TV, video games, table football, ping pong
Dining

Reviews

10 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
    ‪2 min drive‬
  • Place, Bonanza Golf & Gifts
    ‪3 min drive‬
  • Place, Walt Disney World® Resort
    ‪6 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪34 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 2.2 km (1.4 mi) from Bonanza Golf & Gifts. 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 - 2 min drive - 1.4 km
  • Bonanza Golf & Gifts - 3 min drive - 2.7 km
  • Walt Disney World® Resort - 6 min drive - 4.7 km
  • Disney's Animal Kingdom® Theme Park - 7 min drive - 4.5 km
  • Disney Springs™ - 12 min drive - 13.7 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

About this property

Entire place

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

Family Retreat w/ Heated Pool • Hot tub • Game RM •Near Disney & 10 Mins to ESPN

Welcome to 1 Cherry Tree Lane by Practically Perfect Properties, a 5-bedroom, 5-bathroom family retreat in Windsor Hills, just minutes from Walt Disney World, and ESPN Wide Word of Sport. With space for up to 12 guests, a private heated pool and spa, themed bedrooms, and thoughtful family-friendly amenities, this home was designed to make your Disney stay feel joyful, restful, and beautifully easy.

Set within the beautifully maintained, 24-hour manned gated community of Windsor Hills, this English cottage–inspired home offers the best of both worlds: the delight of a Disney vacation and the comfort of a home that feels calm, polished, and genuinely cared for.

From the sweeping two-story foyer to the soft colors, floral touches, and charming details throughout, every space has been thoughtfully prepared for families who want a stay that feels special without ever feeling overwhelming.

Why Families Love It
• Less than 10 minutes to Walt Disney World
• Private heated pool and spa included year-round
• 5 bedrooms and 5 bathrooms
• Themed bedrooms children will remember
• Game room with billiards/table tennis and 3 Xbox consoles
• Family-friendly extras including high chair, pack-n-play, stroller, and pool fence
• Located inside the sought-after Windsor Hills resort community

The Space

The bright kitchen overlooks the private heated pool and spa, making it easy to keep an eye on little swimmers while meals come together nearby. With stainless steel appliances, generous counter space, and an adjacent dining area with seating for eight, gathering for breakfast before the parks or winding down after a full day feels simple and relaxed.

The home’s layout is especially well suited for larger families and multi-generational stays, offering room to spread out, come together, and settle in comfortably.

Sleeping Arrangements

Each bedroom includes its own bathroom, Smart TV, and its own thoughtful personality.
• Primary King Retreat – green, garden-inspired suite with Disney floral touches and ensuite bathroom
• Coastal King Room – serene blue king bedroom with subtle beach-inspired charm and ensuite bathroom
• Up & Away Room – light blue bedroom inspired by Pixar’s Up, with a queen bed and ensuite bathroom
• Hundred Acre Wood Room – cheerful Winnie-the-Pooh–inspired room with twin bunks and a twin trundle
• Princess Room – charming pink bedroom with two twin beds designed for sweet dreams

Three bathrooms include bathtubs, which are especially helpful for little ones at the end of a park day, while two feature walk-in showers.

Amenities

This home has been thoughtfully equipped to make family travel easier and more comfortable. Amenities include:
• Private heated pool and spa
• Game room with billiards/table tennis
• Three Xbox consoles
• Smart TVs in every bedroom
• Fresh, hotel-quality bed linens
• Bath towels and pool towels provided
• Fully equipped kitchen
• Dining area with seating for eight
• High chair
• Pack-n-play
• Stroller
• Pool fence
• Optional stair gates

Windsor Hills Resort Amenities

In addition to the home’s private features, guests also enjoy access to Windsor Hills community amenities, including:
• Large resort-style pool
• Basketball courts
• Tennis courts
• Playgrounds
• Grills and shared outdoor spaces

Location

One of the loveliest things about this home is how easy it makes your stay. You’re close enough for early park mornings, midday breaks, and evening swims back at the house.

Approximate drive times:
• Walt Disney World: less than 10 minutes
• Walmart: 5 minutes
• Target: 10 minutes
• Orlando International Airport: about 30 minutes

Good to Know

This home is best suited for families and respectful groups looking for a comfortable, thoughtfully prepared place to enjoy time together. Windsor Hills is known for being quiet, secure, and especially family-friendly, making it a lovely fit for guests who value both fun and peace of mind.

A Stay to Remember

Guests return not only for the location, but for the feeling this home leaves with them: cared for, comfortable, and ready for memory-making. It’s the kind of place where children remember their Disney house, family traditions begin, and parents get to exhale a little, too.

At Practically Perfect Properties, we believe where you stay shapes how you remember your trip. And here, every detail is thoughtfully in place for something wonderful to begin.

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 Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney?

The closest beach to Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney is Getaway Glen (8.2 km).

Does Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney have a pool?

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

What luxury perks are available at Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney?

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

What makes Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney a romantic place to stay?

1 hot tub, private pools, and private balconies all help set the scene for a sizzling getaway at Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney.

Is Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney family-friendly?

You bet! With amenities such as an arcade, laundry facilities and travel cots, it's no surprise that Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney is a winner with our family travellers.

Is there a private hot tub at Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney?

Yep, there is a hot tub.

Is there a free airport shuttle available at Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney?

No, Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney does not offer an airport shuttle service.

What time are check-in & check-out at Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney?

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

Are pets allowed at Family Retreat w/ Heated Pool, Hot tub & Spa Near Disney?

No, pets are not allowed.

Family Retreat w/ Heated Pool • Hot tub • Game RM •Near Disney & 10 Mins to ESPN Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 107 out of 115 reviews
Rating 8 - Good. 7 out of 115 reviews
Rating 6 - Okay. 1 out of 115 reviews
Rating 4 - Poor. 0 out of 115 reviews
Rating 2 - Terrible. 0 out of 115 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Lindsay S.

Liked: Cleanliness
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

10/10 Excellent

Katherine K., Liberty Township

Liked: Cleanliness
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

8/10 Good

Jodi Q.

Liked: Cleanliness
We had a pleasant stay!
Stayed 7 nights in Dec 2025

10/10 Excellent

Stacie

Liked: Cleanliness
Wonderful property and location. Well suited for multiple families. Great amenities. Teens loved the game room and water slides. Excellent, easy communication with management/owners regarding checkin, etc. Only recommendation would be to stock a few more staples. Needed to purchase more dishwasher detergent, trash bags, tinfoil and toiletries for bathrooms. Otherwise, I would highly recommend and use again in the future.
Stayed 3 nights in Dec 2025

10/10 Excellent

Wayne M.

Liked: Cleanliness
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

10/10 Excellent

laura s.

Liked: Cleanliness
We had a wonderful vacation at this home! It was exactly as pictured, and the ice machine was a huge hit. The kids loved starting their mornings with a swim in the pool right after breakfast.The beds were very comfortable, and the bedrooms were spotless. The spacious living room gave us plenty of room to relax and enjoy time together.We appreciated the abundance of towels—both in the bathrooms and extra in the linen closet. Another thoughtful touch was the stroller available at the house, which was a lifesaver for our Disney days.The Host answered any questions I had during our stay. And was very prompt on a response. Overall we had a wonderful time & Hope to be back soon!!
Stayed 9 nights in Aug 2025

10/10 Excellent

Nori B.

Liked: Cleanliness
Great stay at this wonderful property! No issues with checking in and getting settled. The house was clean, well decorated and all 5 rooms and beds comfortable. Pool was great and outdoor seating was perfect. Any questions / minor issues ( like adjusting temperature in house) were very quickly addressed by the owner and then property manager onsite. We would stay again! Highly recommended
Stayed 9 nights in Jul 2025

10/10 Excellent

Ashley L.

Liked: Cleanliness

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

10/10 Excellent

Chrissie M.

Liked: Cleanliness

Hurry Up And Stay Here!

If you are looking for a gorgeous, spacious house for your Orlando stay, book here! The house is well-suited for a big group, with everything you need to relax or make the short drive to Disney! There are lots of kitchen supplies like pots and pans, plates, dishes, etc. We brought our older kids with us and they LOVED the pool, hot tub, game room and the privacy of their own bathrooms with each of their rooms. The host was great, very responsive to questions, and everything in the photos was exactly what we found in the house. If we come back to Orlando again, THIS house is where we will stay.
Stayed 5 nights in Jun 2025

10/10 Excellent

David H.

Liked: Cleanliness

Mr David Hillson

From start to finish the whole process was seem less. The owner is an excellent host, communication was excellent. The house was just as described spotlessly clean and had absolutely everything you could want. The grown up children ie adults thoroughly enjoyed the games room.The swimming pool at the clubhouse was also superb with slides and a brilliant splash pad.The house is in a superb position for Disney only 15 minutes away.We would love to come back one day.Thank you so much.
Stayed 7 nights in May 2025

10/10 Excellent

Doris H.

Liked: Cleanliness

Enjoyably Relaxing

Great for children under 10 years. The community recreation area was fantastic, but the house swimming pool was the 'hit' of the vacation for both parents and children. A great experience.
Stayed 7 nights in May 2025

10/10 Excellent

Gill H.

Liked: Cleanliness

3 generations vacation

Two weeks of Disney fun at Practically Perfect Villa. Great house and pool plenty of room for 5 adults and two small children, close to all Disney attractions even with heavy traffic at time no longer than 25 min drive 15 mins best. Little further to universal. I would recommend staying here.
Stayed 14 nights in Apr 2025

10/10 Excellent

Vonnie V.

Liked: Cleanliness

Family vacation

We really enjoyed our stay at Where Jolly Delight and Magical Memories Unite. The house was well maintained and very clean. We were supplied with phone numbers to reach if we needed anything but never had to use them. The pool temperature was amazing. We used it every day!!! We loved the security with check in and check out of Windsor Hills. The daily activities at the Clubhouse were fun and engaging for our littles. The pool temp at the waterpark was nice as well. The slides were very cold though. We would definitely go back!!!
Stayed 14 nights in Mar 2025

10/10 Excellent

Gail B., Kanata, Ontario, Canada

Liked: Cleanliness

Jolly Delight and Magical Memories!

Our first impression when we walked in was WOW! The place looked exactly like the pictures, but it looked even better in person. It was clean and bright. There is plenty of seating both inside and out by the pool. The kitchen is very well equipped, and we were very pleased to see lots of plastic plates and cups so that we could enjoy pool side dining with no worry of breaking anything. The addition of an outside TV was a bonus. Our grandkiddies were thrilled to be able to watch TV from the pool. All of bedrooms are well kept. There were plenty of bath towels and beach towels as well. The games room was nice. Again, the grandkiddies had a great time there. The owner was very quick to respond to any questions or concerns that popped up and resolved very quickly. I wouldn't hesitate to book this property again, as it had everything we needed, and then some. Magical Memories were certainly made in this wonderful home.
Stayed 10 nights in Mar 2025

10/10 Excellent

Stephanie K.

Liked: Cleanliness

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

10/10 Excellent

Kellie W.

Liked: Cleanliness

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

10/10 Excellent

Emily P.

Liked: Cleanliness

Great family house

This house was perfect for our family (3) MIL and FIL. There was a primary suite on the first floor so my in-laws did have to use the stairs. My husband and I and our son used the bedrooms upstairs. The pool was delightfully heated and we loved having the hot tub as well. There were more than enough bathrooms and space. The only complaint I have is not having enough toilet paper, paper towels, dishwasher tabs, and garbage bags for the entire week, so we had to purchase these. Additionally, we had to buy some laundry detergent because we did utilize the onsite washer and dryer. There also wasn’t foil or cooking spray to utilize for the dishes. Overall though we thoroughly enjoyed our stay and would recommend this property.
Stayed 7 nights in Feb 2025

10/10 Excellent

Dominic B.

Liked: Cleanliness

Nice place-

Convenient location!
Stayed 6 nights in Jan 2025

10/10 Excellent

Bethany J.

Liked: Cleanliness

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

6/10 Okay

rich d., Gloucester

Liked: Cleanliness

Vacation

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

10/10 Excellent

Cheryl R.

Liked: Cleanliness

Disney World Marathon Weekend 2025

My friends and I have been traveling to Walt Disney World for marathon weekend for the last 12 years. We chose this house because of the neighborhood being so close to Disney. There were plenty of rooms and bathrooms available for us. The kitchen was fully stocked with plenty of utensils, pots, cups, etc. so we were able to prepare our meals. The game room garage provided hours of entertainment. We did have an issue with the Jacuzzi, (beyond anyone’s control) but Jenni (homeowner)and Paul (property manager) were quick to resolve this issue for us. This house truly was perfect in every way. We hope to stay here again in the future.
Stayed 5 nights in Jan 2025

8/10 Good

Terri B.

Liked: Cleanliness

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

10/10 Excellent

Carla F.

Liked: Cleanliness

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

10/10 Excellent

Jessica B.

Liked: Cleanliness

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

10/10 Excellent

Sara B.

Stayed 5 nights in Nov 2024