Around the World at Windsor Hills

Photo gallery for Around the World at Windsor Hills

A large outdoor swimming pool surrounded by palm trees and a hotel building.
A front door with a doormat, a chair, a lamp, and a plant.
A dining area with a wooden table set for six, surrounded by chairs. A chandelier hangs above the table, and a potted plant is visible to the side.
A building with a sign reading "Windsor Hills Clubhouse."
A modern kitchen with stainless steel appliances, granite countertops, wooden cabinets, and a dining area with a table and chairs.

Reviews

10 out of 10, Loved by Guests
Top 1% of guest reviews in this area

Highlights

  • Family fun awaits
    Top-rated for families.
  • Cue up the fun
    One of the few properties with an onsite pool table.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Hot tub on site
  • Lanai
  • Private pool
  • Toys
  • On-site fitness center
  • Barbecue grill

Explore the area

View in a map
Kissimmee, FL
  • Place, Mystic Dunes Golf Club
    ‪3 min drive‬
  • Place, Bonanza Golf & Gifts
    ‪4 min drive‬
  • Place, Island H2O Live!
    ‪6 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪33 min drive‬

Rooms & beds

6 bedrooms (sleeps 14)

Downstairs bedroom

1 Queen Bed

Kids room

1 Twin Bunk Bed and 1 Twin Bed

Upstairs bedroom

1 King Bed

Upstairs kids bedroom

2 Twin Beds

Upstairs master

1 King Bed

Upstairs smaller master

1 King Bed

4 bathrooms

Bathroom 4

Upstairs main bath

Upstairs master

Bathtub · Toilet · Shower only

Upstairs smaller master

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Dining area

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About the neighborhood

Kissimmee

Located in Windsor Hills, a neighborhood in Kissimmee, this vacation 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 in the mood for shopping can visit Old Town and Flamingo Crossings Town Center. Traveling with kids? Don't miss Walt Disney World® Resort and Disney's Hollywood Studios®. Spend some time exploring the area's activities, including golfing, swimming, and winery tours.
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Map
Kissimmee, FL

What's nearby

  • Mystic Dunes Golf Club - 3 min drive - 1.7 km
  • Bonanza Golf & Gifts - 4 min drive - 3.4 km
  • Mighty Jungle Golf - 4 min drive - 3.7 km
  • Island H2O Live! - 6 min drive - 4.1 km
  • Orange Lake Golf - 7 min drive - 7.1 km

Getting around

  • Kissimmee Station - 26 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 22 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪El Cafetal Bakery & Restaurant - ‬3 min drive
  • ‪Del Taco - ‬3 min drive
  • ‪IHOP - ‬3 min drive

Frequently asked questions

Does Around the World at Windsor Hills have a pool?

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

How much does it cost to stay at Around the World at Windsor Hills?

As of Oct 28, 2026, prices found for a 1-night stay for 2 adults at Around the World at Windsor Hills on Nov 7, 2026 start from $314, 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.

Is Around the World at Windsor Hills 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 Around the World at Windsor Hills?

Check-in begins at 4:00 PM.

What time is check-out at Around the World at Windsor Hills?

Check-out is at 10:00 AM.

Where is Around the World at Windsor Hills located?

This family-friendly Kissimmee vacation 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.

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. 87 out of 89 reviews
Rating 8 - Good. 2 out of 89 reviews
Rating 6 - Okay. 0 out of 89 reviews
Rating 4 - Poor. 0 out of 89 reviews
Rating 2 - Terrible. 0 out of 89 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We really enjoyed ourselves, I’ve been staying at Windsor resort over 20 years and that’s the best home I’ve stayed in.
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect, clean house for our stay, exactly as described. Nice size house for 3 families with 4 little ones under the age of 5. Great location to stay for Disney trips! Excellent turnaround on all communication.
Stayed 5 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed here for the second time. Great location, Great hosts, Great property. We will be back!
Stayed 7 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host is wonderful & home has everything you need. Our family would definitely return. The neighborhood is in a great location!
Stayed 5 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This stay renewed our belief in VRBO! This property was CLEAN and accurately portrayed in the description (it’s big and roomy). The hosts communicated well from our initial booking through our checkout. Although there was no need to contact the hosts during our stay, we felt we could reach them if anything came up…that was very reassuring. Thank you for a great experience!
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

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

Family Vacation

Our stay was very nice
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

OUR STAY

We enjoyed our stay very much the house was very nice and comfortable
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

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

Windsor

Great place,location and host.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

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

Amazing

This place was better than we could have hoped for and we will remember it as a great part of our vacation!
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

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

Perfect vacation house and location!

We will definitely be staying here again. Everything from communication, the house, the location, was perfect. The owners had the home stocked and clean. We have nothing but great things to say and highly recommend this property.
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

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

Great stay

As advertised. Everything as it should be for a flawless stay.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

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

Great property, ideal for disney parks

First class property and facilities
Stayed 11 nights in Dec 2022
Verified review

10/10 Excellent

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

Clark family vacation

This stay was amazing! The house was very clean and cozy, while the entire neighborhood was well kept up and safe. I loved how quiet the community was. Our property manager was so hospitable and quick to answer our questions. It truly was a home away from home.
Stayed 6 nights in Jul 2025
Verified review

10/10 Excellent

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

Perfect for my family vacation

Place that everything we needed hosts were very accommodating. They let us do early check in, late check out. Even heated the pool. Place was wonderful.
Stayed 4 nights in Dec 2024
Verified review

10/10 Excellent

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

Brilliant house for our family group holiday

Around the World was a great base for our big family holiday - comfy, spacious and very well set up as a holiday home. Everything we needed had been thought of and the hosts were really quick to respond to any queries. Around the World is a great base for exploring the parks and everything else Orlando has to offer.
Stayed 10 nights in Apr 2025
Verified review

10/10 Excellent

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

Great house

The house overall was really good. It was really spacius for our big family. We enjoyed the stay a lot especially the pool . The house was really clean and comfortable.
Stayed 7 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House had everything we needed. Very well equipped kitchen. Lots of supplies. Bedrooms suited our family of 6 adults and 4 kids perfectly. Pool, hot tub and games room were loved by all. Very close to the resort, which was great. Very handy for everywhere we wanted to go.Communication with owners was great. Would definitely recommend
Stayed 14 nights in Dec 2025
Verified review

10/10 Excellent

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

Excellent Property

This was an exceptional property to stay at. Lots of room for our family of 11. The house had everything you could want to make your holiday special. The host was extremely easy to work with and was most accommodating
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

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

Great House Very Clean and Very Accurate Pictures

I have stayed in over 10 VRBO houses in the Orlando area and this is by far our favorite. Pictures are accurate but much better in person. Host was very accommodating.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

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

Great

Loved the house, pool, hot tub, all the extras and the resort. Owners very easy to communicate to
Stayed 5 nights in Oct 2024
Verified review

10/10 Excellent

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

Great Family Vacation

Wonderful home. Communication with the owner was fast and pleasant. Very nicely laid out and in a very safe and inviting community. Walmart just up the street and plenty of great restaurants within several minutes. Highly recommended!
Stayed 9 nights in Apr 2023
Verified review

10/10 Excellent

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

Vacation on spring break 2025

Everything was great, house was like pictures. It was very clean and we enjoyed everything it had to offer. And yes, we made sure it looked the way we found it when we left. Thanks for the opportunity to book this home. Neighbors were so friendly.
Stayed 3 nights in Apr 2025
Verified review

8/10 Good

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

Excellent!

We love our stay. Nice, clean, and located close to our Walt Disney Epcot destination. Also conveniently close to Walmart to grab groceries and necessities. And Dave, our host, was very responsive and accommodating. Thank you Dave.
Stayed 5 nights in Aug 2024
Verified review

10/10 Excellent

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

Nice Family Home

Great Stay! Well laid out and furnished! No issues at all ! Conveniently located near Disney World with lots of Restaurants nearby! Gated security! Great communication with owner who seems very motivated to be sure you had a perfect stay! 👍
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

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

Nationals Stay

I have been competing in AAU Nationals since 2011, this has been by far one of the best houses my team has stayed over the years. Clean, up to date and good communication.
Stayed 5 nights in Jun 2025
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