Florida may have travel restrictions in place due to COVID-19.

Find out moreOpens in new tab or window

Hotels in Windsor Hills, Orlando

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Windsor Hills hotels and places to stay

Windsor Hills Resort Homes
3.5 out of 5
2583 Archfeld Blvd, Kissimmee, FL
Get Rates
4/5Very Good! (2 reviews)
Better than expected

"This is a great complex! This pictures actually don’t do justice. Loved the house and the complex with the pool and slides. The house was perfect for our group of 15. It was also in a good location. Close to Disney, Walmart and lots of restaurants. The check in process was very time consuming and ..."…"

Reviewed on Mar. 4, 2020

Windsor Hills Resort Homes
Windsor Hills Resort by Global Resort Homes
3.5 out of 5
7600 Comrow St, Kissimmee, FL
Get Rates
3.7/5Good! (19 reviews)

"Property was in an excellent location to go to all the theme parks."…"

Reviewed on Dec. 14, 2019

Windsor Hills Resort by Global Resort Homes
Disney at Your Doorstep by VillaDirect
4 out of 5
2821 Almaton Loop, Unit 403, Kissimmee, FL
Get Rates
Disney at Your Doorstep by VillaDirect

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
The Perch at Windsor Hills: View of Disney Fireworks. Water Park. Movie Theatre
4.6/5Wonderful! (54 reviews)
Great Stay at the Perch

"The property is an ideal location if you want to stay off of resort accommodations and have the comforts of home. It was very clean and had everything you would need. The pool and the new water park and slides were great entertainment for our kids. Valeria was very quick to answer any questions we ..."…"

Reviewed on Apr. 14, 2020

The Perch at Windsor Hills: View of Disney Fireworks. Water Park. Movie Theatre
5-10 Min. To Disney - Gated Resort With Large Heated Pool And Slide
Get Rates
4.8/5Exceptional! (28 reviews)
Great location

"Clean, comfortable and very close to Disney! We (family) loved our 4 day weekend at this beautiful condo. The condo was clean and had everything we needed!"…"

Reviewed on Sep. 7, 2020

5-10 Min. To Disney - Gated Resort With Large Heated Pool And Slide
Resort Style Living 2 Miles From Disney World
7663 Fitzclarence St, Kissimmee, FL
Get Rates
4.9/5Exceptional! (27 reviews)
Great place, great location

"Great place and great location. Easy access everywhere. Owner communicates fast and very reliable. Everything worked as advertised."…"

Reviewed on Aug. 27, 2020

Resort Style Living 2 Miles From Disney World
3 BR 2 Miles to Disney, Pool, Spa, Water Park, Game Room, Free Wifi and More
4.6/5Exceptional! (46 reviews)
Disney October 2020

"After a mix up with the check-in it was a great stay."…"

Reviewed on Oct. 19, 2020

3 BR 2 Miles to Disney, Pool, Spa, Water Park, Game Room, Free Wifi and More
5br/5ba And 4 Ensuites With Brand New Furniture/south Faced Pool And Spa
4.4/5Wonderful! (31 reviews)
Perfect Family Vacation

"The house was perfect, exactly what we wanted. Everyone loved it and the kids had a blast!!"…"

Reviewed on Oct. 19, 2020

5br/5ba And 4 Ensuites With Brand New Furniture/south Faced Pool And Spa
Magnolia Style Condo at Windsor Hills With Disney Theme Bunk Room
Get Rates
4.8/5Exceptional! (36 reviews)
Wonderful, quiet and relaxing

"We spent the day at the parks and it was so nice to come back to a quiet room to relax. I have a small child so a quiet room for her to rest is on the top of my list and it was great! Easy communication, thanks Wendy we’ll be back!"…"

Reviewed on Aug. 25, 2020

Magnolia Style Condo at Windsor Hills With Disney Theme Bunk Room
Luxury 7 Bedroom Pool Home at Disney Resort, 2 Miles to Disney,special Offer
4.5/5Wonderful! (25 reviews)
Great host

"Nice and big place ... owner was very supportive with everything ..."…"

Reviewed on Jun. 8, 2020

Luxury 7 Bedroom Pool Home at Disney Resort, 2 Miles to Disney,special Offer
Don't see what you're looking for?
See all available properties in Windsor Hills
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Windsor Hills Hotels Guide

Expedia.ca offers a selection of 2397 hotels in Windsor Hills. You are sure to find cheap deals and discount rates among them with our Best Price Guarantee. No matter what type of hotel strikes your fancy, we will let you search for your preferred one to accommodate your travel needs.

Expedia.ca will not only save you time, but also money when booking your stay at a hotel in Windsor Hills. Making reservations so you can stay within your budget is easy with us.

Expedia.ca even provides you with a map so you may find hotels in the Windsor Hills neighborhood you prefer.

Go ahead. Enter your travel dates to view the best offers on hotel rooms in Windsor Hills, Orlando now!

Frequently asked questions

What's it like in Windsor Hills?
Travelers will be sure to enjoy their time in Four Corners’s Windsor Hills neighborhood.
Where is the best place to stay in Windsor Hills?
Based on our traveler data, 3 BR 2 Miles to Disney, Pool, Spa, Water Park, Game Room, Free Wifi and More is one of the top choices for your stay in Windsor Hills. This resort offers private pools and free WiFi. Other good choices for your stay in the neighborhood include Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 10 and Windsor Hills Resort by Global Resort Homes.
How many hotels will I find in the Windsor Hills area?
Expedia has 2425 hotels and other accommodations in Windsor Hills to choose from, making this an ideal home base for exploring the greater Four Corners area.
If I need to cancel my hotel reservation in Windsor Hills, will I receive a refund?
Yes, most hotel room reservations are fully refundable as long as you cancel prior to the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and get a refund within a 24-hour period of booking. Plug in your dates, click on “Search”, then use the “free cancellation” filter to review the best deals available in Windsor Hills.
What are the top things to see and do in Windsor Hills?
Don’t miss favorite places to visit in the surrounding area, such as Disney’s Animal Kingdom® Theme Park, ESPN Wide World of Sports, and Disney’s Blizzard Beach Water Park. While you’re out sightseeing in Four Corners, be sure to visit other sights like Island H2O Live! or Melt-Away Bay.

Recent Reviews in Windsor Hills