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Minutes from Disney - a Practically Perfect, Whimsical English Cottage Retreat

Family-friendly vacation home with a water park and an outdoor pool

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Eat-in-kitchen for four overlooking the pool
Beautiful five bedroom, five bathroom Windsor Hills Vacation Pool Home
Two-story foyer welcomes you to "Cherry Tree Lane"
Well-lit formal dining room for eight
Cozy, comfortable and spacious great room featuring the art of David Buckley

Reviews

10 out of 10, Loved by Guests
5 bedrooms5 bathroomsSleeps 112400 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Rooms & beds

5 bedrooms (sleeps 11)

Blue King Bedroom (Second Floor)

1 King Bed

Green King Bedroom (First Floor)

1 King Bed

Princess Bedroom (Second Floor)

2 Twin Beds

Star Wars Two Twin & Trundle (First Floor)

3 Twin Beds

Yellow Queen (First Floor)

1 Queen Bed

5 bathrooms

Blue Bathroom

Bathtub or shower · Toilet

Blue Star Wars Bathroom

Bathtub · Toilet

Green Bathroom

Toilet · Shower only

Pink Princess Bathroom

Bathtub or shower · Toilet

Yellow Bathroom

Bathtub or shower · Toilet · Hair dryer

Spaces

Deck or patio
Kitchen
Separate dining area
Dining area

About this property

Minutes from Disney - a Practically Perfect, Whimsical English Cottage Retreat

Practically Perfect Properties
Where Jolly Delight & Magical Memories Unite
Step into a storybook stay with Practically Perfect Properties. 1 Cherry Tree Lane is a whimsical English-cottage–inspired retreat just minutes from Walt Disney World and nestled inside the 24-hour manned, security-gated Windsor Hills community.

This thoughtfully designed 5-bedroom, 5-bathroom home sleeps up to 12 and was created for families who want Disney magic without chaos—a place that feels joyful, calm, and genuinely cared for.

***A Home Designed for Families (and Peace of Mind)
From the moment you enter the sweeping two-story foyer, you’ll feel it: this is not a cookie-cutter rental. Soft colors, floral touches, and charming details create an atmosphere that’s playful yet polished—magical without being overwhelming.

The bright, sunny kitchen overlooks the private heated pool and spa, making it easy for parents to relax while children swim. Stainless steel appliances, generous counter space, and an adjacent dining room with seating for eight make meals together easy.

***Five Thoughtfully Themed Bedrooms (One Bath Per Bedroom)
Every bedroom has its own bathroom, its own Smart TV, and its own personality:
-Primary King Retreat – Green, garden-inspired suite with Disney florals and ensuite
-Coastal King Room – Blue, Disney-beach–themed king bedroom with ensuite
-Up & Away Room – Light blue Pixar’s UP–themed queen bedroom with ensuite
-Hundred Acre Wood Room – Cheerful yellow Winnie-the-Pooh–themed bunk room with twin bunks and twin trundle
-Princess Room – Pink, charming two, twin bedroom fit for royal dreams
Three bathrooms feature bathtubs (perfect for little ones), while two offer walk-in showers.

***Private Fun + Resort-Style Amenities
-Private heated pool & spa (included year-round)
-Converted game room with billiards/table tennis and three Xbox consoles
-Fresh, hotel-quality bedroom linens and bath & pool towels provided
-High chair, pack-n-play, stroller, pool fence, and optional stair gates available

Just steps away, enjoy the Windsor Hills resort amenities:
-Huge community pool
-Basketball & tennis courts
-Grills, playgrounds, and more

***Location That Makes Disney Easy
-Less than 10 minutes to Disney
-5 minutes to Walmart
-10 minutes to Target
-approximately 30 minutes to Orlando International Airport
You’re close enough for early park mornings—and close enough to come “home” for afternoon naps and evening swims.

***A Calm, Family-Focused Community
Windsor Hills is known for being quiet, secure, and family-friendly. This home is ideal for families and multi-generational groups who value comfort, care, and respectful enjoyment.

***Why Guests Return
Families return because this home feels intentional—clean, well-maintained, and designed with heart. It’s a place where traditions start, where children remember their Disney house, and where parents actually get to relax.

Practically Perfect Properties isn’t just a place to sleep between park days.
It’s where jolly delight and magical memories truly unite.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Hot Tub
Kitchen
Washer
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
Please Inquire
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Pets

No pets allowed
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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
Onsite parties or group events are strictly prohibited
Note from host: Please Inquire
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock

We should mention

A car is required for transportation to and from this property

About the neighborhood

Kissimmee

Located in Windsor Hills, a neighborhood in Kissimmee, this vacation home is near theme parks. 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. Traveling with kids? Don't miss Disney's Hollywood Studios® and Disney's Blizzard Beach Water Park. Take an opportunity to explore the area for water adventures such as swimming and other activities like golfing.
Map
Kissimmee, FL

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
  • Epcot® - 11 min drive - 10.5 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

Frequently asked questions

Does Where Jolly Delight and Magical Memories Unite have a pool?

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

Is Where Jolly Delight and Magical Memories Unite pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Where Jolly Delight and Magical Memories Unite?

Check-in begins at 4:00 PM.

What time is check-out at Where Jolly Delight and Magical Memories Unite?

Check-out is at 10:00 AM.

Where is Where Jolly Delight and Magical Memories Unite located?

This family-friendly Kissimmee vacation home is located in Windsor Hills, within 3 mi (5 km) of Island H2O Live!, Walt Disney World® Resort, and Mystic Dunes Golf Club. Old Town and Disney's Hollywood Studios® are also within 6 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 105 out of 113 reviews
Rating 8 - Good. 7 out of 113 reviews
Rating 6 - Okay. 1 out of 113 reviews
Rating 4 - Poor. 0 out of 113 reviews
Rating 2 - Terrible. 0 out of 113 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

8/10 Good

Jodi Q.

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

10/10 Excellent

Wayne M.

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

10/10 Excellent

Stacie

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

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

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

10/10 Excellent

Dominic B.

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

Nice place-

Convenient location!
Stayed 6 nights in Jan 2025

10/10 Excellent

TOBY F.

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

10/10 Excellent

Nori B.

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

Carla F.

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

10/10 Excellent

Doris H.

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

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

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

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

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

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

10/10 Excellent

Nicole B.

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

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

10/10 Excellent

tammy H.

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

10/10 Excellent

David W.

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

10/10 Excellent

Gill H.

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

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

Sarah B.

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

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

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

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

10/10 Excellent

Verified traveler

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

April Vacation 2024

This is our second year in a row staying here. It was like coming home. We love the house!!!
Stayed 8 nights in Apr 2024

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

About the host

Hosted by Practically Perfect Properties

Host profile image
As a travel agent, making Disney dreams come true is my passion! Having a vacation home is one more way of making magic!
Also, for fifteen years I dreamed of owning a vacation home near Walt Disney World. My family and I were able to purchase this home in May, 2019 when my eldest chid and only daughter participated in the Disney College Program. While her experience was cut short due to the pandemic, we were able to quarantine in Florida, enjoy the weather and pool, and truly appreciate our beautiful vacation home for the blessing that it is. As a family of six, we continue to look forward to future vacations when we can spread out in our own rooms, and reunions when we can be joined by grandparents, aunts, uncles, cousins and friends in our beautiful home!

Why they chose this property

We love the security and upkeep of Windsor Hills. When in town, we take advantage of the proximity to local attractions like Walt Disney World, Universal Studios, Sea World and more! We appreciate that there's a Walmart and Starbucks within minutes of the house! You won't go hungry here - there are dozens of restaurants within a 10-minute drive and you can always get food delivery directly to the house.

What makes this property unique

Windsor Hills is unparalleled in its proximity to Walk Disney World and the amenities are outstanding. When coupled with the fresh and clean condition of the home, you can be assured, a delightful vacation awaits you and your family!

Languages:

English

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