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Encanto, Skee-Ball & Peter Pan *Windsor Whimsy* 6 BR

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Drive down the beautiful tree-lined street to our home and conveniently park directly in front of the house in the driveway.
Gorgeous magnolias, spanish moss laden oaks, and towering palm trees welcome you to the neighborhood. Just behind the front door lies the rest, relaxation, and memories you’ve been waiting for.
With vintage Disney decor, the living room will immediately capture your imagination and invite you to “leave today and enter the world of yesterday, tomorrow, and fantasy” as Walt Disney would say.
Comfort, convenience, and beauty were considered in every design and decor choice. Our hope is that the small, thoughtful details scattered throughout the house invite you into a time to relax and connect.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
6 bedrooms4 bathroomsSleeps 13260.1 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Kissimmee, FL
  • Place, Bonanza Golf & Gifts
    ‪3 min drive‬
  • Place, Walt Disney World® Resort
    ‪6 min drive‬
  • Place, Disney Springs™
    ‪12 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪34 min drive‬

Rooms & beds

6 bedrooms (sleeps 13)

Aladdin King Suite

1 King Bed

Beauty and the Beast Queen Room

1 Queen Bed

Cinderella King Suite

1 King Bed

Encanto Kid’s Room- Twin over Full Bunk

1 Single Bed and 1 Double Bed

Mickey Mouse Kid’s Room- Twin over Twin Bunk

1 Single Bunk Bed

Peter Pan Queen Room

1 Queen Bed

4 bathrooms

Aladdin Room Ensuite Bathroom

Toilet · Shower only

Cinderella Room Ensuite Bathroom

Bathtub · Toilet · Shower only

Downstairs Shared Bathroom-Subtle Mickey Mouse Themed

Bathtub or shower · Toilet

Upstairs Shared Bathroom- Mickey Mouse Themed

Bathtub or shower · Toilet

Spaces

Kitchen
Dining area

About this property

Encanto, Skee-Ball & Peter Pan *Windsor Whimsy* 6 BR

Step into the magic as soon as you walk through the doors of your own private 6 bedroom, 4 bathroom villa. Newly renovated and redecorated, every space has been designed to make special, lifelong memories with family and friends. Every room is whimsically and tastefully themed and loaded with the comforts and conveniences of home. Located in Windsor Hills Resort- a private, 24/7 guarded resort community with free waterpark and zero entry lagoon style pool. Only minutes from Disney theme parks and conveniently located to all other Orlando attractions.

Encanto, Peter Pan, Cinderella and more! Only minutes from Disney parks and all Orlando has to offer our 6 bedroom, 4 bathroom fully themed pool home has everything you need to enjoy your vacation. Whether you choose to relax in your private full size pool with spa, visit the resort community’s lagoon style pool with waterpark and loads of activities, or explore the area with a jam packed day at one of the many local theme parks, you will find our home is the perfect location for any type of day you choose. When evening comes, cook up a dinner in the fully stocked kitchen, eat poolside in the screened in lanai, and retreat to your bedroom for a deep restful sleep in one of the brand new beds with luxurious 100% cotton linens. White noise machines will ensure you aren’t awakened too early from the kids playing Skee-ball, foosball, or Nintendo Switch in the fun and bright Toy Story Themed game room. Windsor Whimsy is sure to be your home base for making memories you will cherish for years!

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
No Smoking or Vaping. No parties. No pets. Resort community quiet hours from 11pm-7am. Driveway only parking for 3 vehicles.
Be respectful of neighbors. Be respectful of home, report any damage or problems immediately.
Signed rental agreement and $500 refundable security deposit is required.

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
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, a first aid kit and a deadlock

About the area

Kissimmee

Located in Windsor Hills, a neighbourhood in Kissimmee, this holiday home is near theme parks. Old Town and Flamingo Crossings Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Hollywood Studios®. Travelling with kids? Don't miss Disney's Blizzard Beach Water Park and Epcot®. Power boating and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
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Map
Kissimmee, FL

What's nearby

  • Bonanza Golf & Gifts - 3 min drive - 2.7 km
  • Walt Disney World® Resort - 6 min drive - 5.4 km
  • Disney's Animal Kingdom® Theme Park - 7 min drive - 4.5 km
  • Disney Springs™ - 12 min drive - 13.7 km
  • Magic Kingdom® Park - 14 min drive - 15.3 km

Getting around

  • Kissimmee Station - 25 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 22 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Starbucks - ‬2 min drive
  • ‪Del Taco - ‬3 min drive
  • ‪Osaka Bay Buffet - ‬3 min drive
  • ‪Sickies Garage Burgers & Brews - ‬3 min drive

Frequently asked questions

Is Encanto, Skee-Ball & Peter Pan *Windsor Whimsy* 6 BR pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Encanto, Skee-Ball & Peter Pan *Windsor Whimsy* 6 BR?

As of 21 Apr 2026, prices found for a 1-night stay for 2 adults at Encanto, Skee-Ball & Peter Pan *Windsor Whimsy* 6 BR on 28 June 2026 start from AU$497, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Encanto, Skee-Ball & Peter Pan *Windsor Whimsy* 6 BR?

On-site parking is available at the property.

What time is check-in at Encanto, Skee-Ball & Peter Pan *Windsor Whimsy* 6 BR?

Check-in begins at 4:00 PM.

What time is check-out at Encanto, Skee-Ball & Peter Pan *Windsor Whimsy* 6 BR?

Checkout is at 10:00 AM.

Where is Encanto, Skee-Ball & Peter Pan *Windsor Whimsy* 6 BR located?

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

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
we loved our stay at Windsor Whimsy! It was the perfect setting for our multigenerational visit to Orlando and Disney. The theming of the rooms was so cute and there was plenty of space for us to relax and enjoy our time together.
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Marie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location and amenities
Stayed 6 nights in Jul 2025
Verified

10/10 Excellent

Dawn C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect house for our family, we loved all of the Disney decorations, themed rooms and especially the playroom. There were "ears and bubbles" on the table for the kids when we checked in. Krissi and Keith were easy to reach and helped solve a mishap very quickly and professionally. I would highly recommend this house if you're planning a trip to Orlando and the parks.
Stayed 13 nights in Feb 2026
Verified

10/10 Excellent

Jessica K.

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

Wonderful!!!

The house is decorated beautifully! My kids loved the pool. I loved the coffee area. 5 stars all the way around!!!
Stayed 8 nights in May 2024
Verified

10/10 Excellent

Amy L.

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

Magical getaway

This property was absolutely wonderful and what we needed. It was clean and so comfortable. The rooms were fun and tastefully decorated. Our 4 year old son had so much fun with the toy room— that was outstanding and wonderful for his little imagination. Krissi was such a kind host and reached out several times. We hope to stay there again!
Stayed 5 nights in Jul 2024
Verified

10/10 Excellent

Amelia T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved this house so much for our family Thanksgiving trip. I originally chose Windsor Hills for the community amenities—the playgrounds, the pool, the water park—but I’m so glad we booked this particular home. I expected we’d spend most of our time out in the community areas, but we ended up hanging out at the house constantly because it was just that comfortable and fun.The open layout was perfect for our big, blended family (including divorced grandparents who really needed separate lounging spaces!). There were multiple seating areas and plenty of room for everyone to spread out without feeling disconnected.My favorite part was the kids’ setup. The toys, themed rooms, and little surprises throughout the house were a huge hit. Our 15-month-old and almost-3-year-old played nonstop, and even our 13-year-old was totally comfortable in her own room.We reached out to the hosts a couple of times and they were incredibly responsive and helpful. When the coffee maker stopped working, they had a brand-new one delivered within hours—truly above-and-beyond service.This was the perfect home base for our trip, and we’d absolutely stay here again.
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Sarah F.

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

Family Trip to Disney

We took our girls to Disney to celebrate a graduation for one, and give our little her first trip! The house was perfect! We had too many people to utilize hotels for the space needed, and knew we wanted a house but also Disney charm. This is it! The decor is adorable and fun for all ages without being overwhelming, there’s subtle charm everywhere! We utilized the pool for our youngest, weather was chillier our week but it was great to come back to a quiet spot and relax. The only reason for 4 stars on the check in process was just the length of time, we had a long line ahead of us but that’s nothing the owner could control. Once you’re checked in tho. It’s very smooth to get in and out of the property and feels very safe. Our family had a magical trip, Disney property is so close it didn’t feel like it was a burden at all to commute between the two, restaurants are available nearby and the amenities of the house were wonderful. We hope to come again!
Stayed 8 nights in Mar 2025

About the host

Hosted by Krissi and Keith Callahan

Host profile image
Hi! We are the Callahan Family! Our family of seven loves adventuring together and meeting new people. We enjoy exploring Florida, are huge Disney fans, and are so excited to share our vacation home with you. Renovating and decorating this home has been a family affair and we have tried to think of everything to make your stay comfortable, fun, convenient, and memorable! We want your stay to be perfect and are available to connect with guests directly during the whole process- from booking to check-out. We hope you make magical memories at Windsor Whimsy and enjoy it and all the area has to offer!

Why they chose this property

Location, Location, Location! We bought this home because of its incredible location to Disney theme parks and Orlando’s central location to some of the best Florida has to offer. Located in the well established, safe, and beautiful community of Windsor Hills Resort our home is only 8 minutes from Animal Kingdom and 12-15 to Magic Kingdom, Hollywood Studios, and EPCOT, making it as close and convenient as a Disney resort with more space and more amenities. A short half hour drive gets you to all the action at Universal theme parks and Sea World. Driving a little over an hour will get you to the Atlantic Beaches and Kennedy Space Center or drive an hour and 40 minutes to get to the gulf side beaches in Clearwater- repeatedly voted some of the best beaches in the world. Hundreds of shopping, entertainment, and dining options are minutes away.
Windsor Hills Resort is a 24/7 secure gated community with tons of amenities. It boasts a zero-entry lagoon style swimming pool, waterpark with waterslides, splash pad, water bucket and fun poolside planned activities and events. Also within the community are multiple playgrounds, including one fully fenced castle themed playground and a lighted sports complex with pickleball, tennis courts, basketball courts, volleyball court, and putting green. At the community center, you’ll find an arcade/game room, a theatre playing nightly movies, fitness center, convenience store, and cafe serving poolside drinks, simple meals, snacks, and ice cream.

Languages:

English
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