Find hotels in Windsor Hills, Orlando

Most hotels are fully refundable. Because flexibility matters.

Save 10% or more on select stays with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide.

Filter by

Popular filters
Guest rating
guestRating-
guestRating-45
guestRating-40
guestRating-35
Star rating
Payment type
Property type
Neighborhood
regionId-178294
regionId-800087
regionId-10870
regionId-6034611
regionId-6360417
regionId-6361034
regionId-6209488
regionId-800089
regionId-6151795
regionId-7927
regionId-6176523
regionId-5194573
regionId-177664
regionId-6126579
regionId-5965
regionId-7902
regionId-7898
regionId-602896
regionId-6360395
regionId-6301
Popular locations
poi-28.38728,-81.567156:6034120
poi-28.41619,-81.5812:6049246
poi-28.47788,-81.470642:6049239
poi-28.416459,-81.581169:6034436
poi-28.473012,-81.467757:6347698
poi-28.410385,-81.461968:502142
poi-28.371064,-81.518143:502131
poi-28.417664,-81.581215:6123797
poi-28.359718,-81.591316:6123780
poi-28.424379,-81.469927:6034972
poi-28.371649,-81.548822:6123778
poi-28.368902,-81.519263:6034242
poi-28.479718,-81.470101:6277909
poi-28.405126,-81.463937:6068683
poi-28.474169,-81.45064:6154309
poi-28.60294,-81.20121:6034977
poi-28.539237,-81.383875:6069361
poi-28.445681,-81.394739:502138
poi-28.357246,-81.560591:502132
poi-28.329927,-81.515923:6128179
Meal plans available
Amenities
Accessibility
Traveler experience
7766 5-bedoom Orlando Vacation Home-windsor Hills

7766 5-bedoom Orlando Vacation Home-windsor Hills
3.5 out of 5
7766 Basnett Circle, Kissimmee, FL, 34747
Get rates
Windsor Hill Resort

Windsor Hill Resort
3 out of 5
2562 Renshaw St, Kissimmee, FL, 34747
Get rates
Karen's Windsor Hill's Resort Condo

Karen's Windsor Hill's Resort Condo
3.5 out of 5
2778 Almaton Loop #401, Bldg 1, Kissimmee, FL, 34747
4/5 Very Good! (1 review)
"Très beau resort avec plein de choses à faire. Le condo doit être rénové."

Reviewed on May 28, 2022

Get rates
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Sign up, it's freeSign in
Disney at Your Doorstep by VillaDirect

Disney at Your Doorstep by VillaDirect
4 out of 5
2821 Almaton Loop, Unit 403, Kissimmee, FL, 34747
Get rates
Villa in Windsor Hills Resort 1709

Villa in Windsor Hills Resort 1709
7811 Beechfield Street, Kissimmee, FL, 34747
Get rates
9 MILES FROM DISNEY! 3BR/2BA w/ Water Park, Heated Pool, Arcade, Gym & More

9 MILES FROM DISNEY! 3BR/2BA w/ Water Park, Heated Pool, Arcade, Gym & More
Kissimmee, FL
4.8/5 Exceptional! (79 reviews)
Just as it is described
"This place was great. Very clean. Directions to the place was exact. Amenities such as the pool area and game room were wonderful. Beds were fairly comfortable. The only complaint I had was that on the last night there we kept hearing a loud noise and couldn't exactly determine which unit around ..."

Reviewed on Sep 6, 2022

Get rates
Lakeview Gardens

Lakeview Gardens
4 out of 5
7660 Comrow Street #305, Kissimmee, FL, 34747
4.5/5 Wonderful! (2 reviews)
"Family Friendly, Unit had Pack N Play, gaming system and a community pool!"

Reviewed on Jan 19, 2022

Get rates
Windsor Hills - Large 3BR/2BA - 5 Min to Disney

Windsor Hills - Large 3BR/2BA - 5 Min to Disney
Kissimmee, FL
4.7/5 Exceptional! (105 reviews)
Fantastic 2 week stay at Windsor Hills
"The appartment is in a lovely, secure gated community with a fantastic swimming pool on site with water slides. Really good for kids. The appartment itself was a really good size and nicely decorated. We found the aircon to be a god send with the summer orlando heat outside. Location is great. It's ..."

Reviewed on Sep 13, 2022

Get rates
Dream Disney Family Vacation,one of best resort 2 miles to Disney, space for 8

Dream Disney Family Vacation,one of best resort 2 miles to Disney, space for 8
Kissimmee, FL
4.5/5 Wonderful! (81 reviews)
Great spot to stay
"Great communication from the owner throughout. Condo was clean and as described. Kitchen is well stocked with cooking supplies, including pots/pans/colander. Easy check-in process, and once checked in, easy to get in and out of the resort. The pool area is great, there's a sloped "beach" for young ..."

Reviewed on Jul 7, 2022

Get rates
New Water Park is Now OPEN!!! Spend the summer at Disney🏝

New Water Park is Now OPEN!!! Spend the summer at Disney🏝
Kissimmee, FL
4.9/5 Exceptional! (135 reviews)
Great Stay
"Communication with property owners was excellent! They reached out several times checking in and making sure that everything was ok. The property was exactly as listed, plenty of natural light, decorated very cute with Disney theme in the kids room. We didn't use the extra room, but the master bed ..."

Reviewed on Sep 7, 2022

Get rates
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 information

Number of reviews 404
Accommodation 1745 hotels
Lowest Price
Highest Price

Frequently asked questions

What's it like in Windsor Hills?

Travelers will be sure to enjoy their time in Kissimmee's Windsor Hills neighborhood.

Where is the best place to stay in Windsor Hills?

Based on our traveler data, Windsor Hill Resort is one of the top choices for your stay in Windsor Hills. This 3-star aparthotel offers a golf course and a restaurant. Another good choice for your stay in the neighborhood is Windsor Hills by Nova.

How many hotels will I find in the Windsor Hills area?

Expedia has 1746 hotels and other accommodations in Windsor Hills to choose from, making this an ideal home base for exploring the greater Kissimmee 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 "fully refundable" filter to review the best deals available in Windsor Hills.

Where can I learn more about changing or cancelling my trip to Windsor Hills?

For more details about picking new dates or cancelling your trip to Windsor Hills, head over to our customer service page.

What are the top things to see and do in Windsor Hills?

A few places to visit in the area around Windsor Hills include Disney's Animal Kingdom® Theme Park, Island H2O Live!, and Melt-Away Bay. While you're out sightseeing in Kissimmee, be sure to visit other sights like Disney's Blizzard Beach Water Park or Disney's Winter Summerland Miniature Golf Course.

Read verified traveler reviews of recently booked hotels in Windsor Hills: See where other travelers loved staying.

  • Amazing Top Rated Villa! Saltwater Pool-Game Room, Water Park, Grill & Baby Gear

    Amazing Top Rated Villa! Saltwater Pool-Game Room, Water Park, Grill & Baby Gear

    5/5 Excellent
    Birthdays
    "This home layout worked well for our family to get together to celebrate our grandchildrens' birthdays. It was clean and well equipped. We enjoyed both the pool at the house and the community pool. The hosts provided quick response to any questions."
    A verified traveler stayed at Amazing Top Rated Villa! Saltwater Pool-Game Room, Water Park, Grill & Baby Gear
    Posted 8 days ago
    Amazing Top Rated Villa! Saltwater Pool-Game Room, Water Park, Grill & Baby Gear
  • Family-Friendly Condo Near Disney w/ a Pool, Waterpark, & Bunk Beds for the Kids

    Family-Friendly Condo Near Disney w/ a Pool, Waterpark, & Bunk Beds for the Kids

    5/5 Excellent
    Excellent
    "Great place to stay"
    A verified traveler stayed at Family-Friendly Condo Near Disney w/ a Pool, Waterpark, & Bunk Beds for the Kids
    Posted 8 days ago
    Family-Friendly Condo Near Disney w/ a Pool, Waterpark, & Bunk Beds for the Kids
  • ***** Minutes To Walt Disney World's Front Gate *****

    ***** Minutes To Walt Disney World's Front Gate *****

    5/5 Excellent
    Heaven
    "We loved our stay! The condo was great, pool was amazing, property was nice, and convenient to shops, food and Disney parks! Wish it would have had elevators with the kids but would definitely book again!"
    A verified traveler from South Bend, IN USA stayed at ***** Minutes To Walt Disney World's Front Gate *****
    Posted 12 days ago
    ***** Minutes To Walt Disney World's Front Gate *****
  • Windsor Hills - Large 3BR/2BA - 5 Min to Disney

    Windsor Hills - Large 3BR/2BA - 5 Min to Disney

    5/5 Excellent
    Fantastic 2 week stay at Windsor Hills
    "The appartment is in a lovely, secure gated community with a fantastic swimming pool on site with water slides. Really good for kids. The appartment itself was a really good size and nicely decorated. We found the aircon to be a god send with the summer orlando heat outside. Location is great. It's located close to Disney and there are plenty of places to eat nearby. Walmart is very close by and there is a Target a 10 minute drive away. We really enjoyed our stay at and would definitely stay again. Thanks!"
    A verified traveler stayed at Windsor Hills - Large 3BR/2BA - 5 Min to Disney
    Posted 3 weeks ago
    Windsor Hills - Large 3BR/2BA - 5 Min to Disney
  • Family friendly Windsor Hill Resort condo, 10 minutes to Disney, Xbox Game

    Family friendly Windsor Hill Resort condo, 10 minutes to Disney, Xbox Game

    5/5 Excellent
    All you need on a vacation
    "The condo has everything you need on vacation. The communication with owners was good. Very resp"
    A verified traveler stayed at Family friendly Windsor Hill Resort condo, 10 minutes to Disney, Xbox Game
    Posted 1 month ago
    Family friendly Windsor Hill Resort condo, 10 minutes to Disney, Xbox Game
  • New Water Park is Now OPEN!!! Spend the summer at Disney🏝

    New Water Park is Now OPEN!!! Spend the summer at Disney🏝

    5/5 Excellent
    Great Stay
    "Communication with property owners was excellent! They reached out several times checking in and making sure that everything was ok. The property was exactly as listed, plenty of natural light, decorated very cute with Disney theme in the kids room. We didn't use the extra room, but the master bed was very comfortable. First time ever my husband didn't toss and turn during a stay away from home! Loved the welcome snacks! We didn't get to sign the guest book because we couldn't find a pen :( We would definitely stay here again!"
    A verified traveler stayed at New Water Park is Now OPEN!!! Spend the summer at Disney🏝
    Posted 1 month ago
    New Water Park is Now OPEN!!! Spend the summer at Disney🏝
  • 9 MILES FROM DISNEY! 3BR/2BA w/ Water Park, Heated Pool, Arcade, Gym & More

    9 MILES FROM DISNEY! 3BR/2BA w/ Water Park, Heated Pool, Arcade, Gym & More

    5/5 Excellent
    Just as it is described
    "This place was great. Very clean. Directions to the place was exact. Amenities such as the pool area and game room were wonderful. Beds were fairly comfortable. The only complaint I had was that on the last night there we kept hearing a loud noise and couldn't exactly determine which unit around us it was coming from to even call and complain about it. After reading the little booklet that comes with check in , even if we figured it out we did not suppose to call security for a noise disturbance but instead you are directed to call the police. This seems like a lot of commotion to cause just to complain to someone about the noise. We decided to put up with it and it lasted for 2 hours. Other than that it was a great place."
    A verified traveler stayed at 9 MILES FROM DISNEY! 3BR/2BA w/ Water Park, Heated Pool, Arcade, Gym & More
    Posted 1 month ago
    9 MILES FROM DISNEY! 3BR/2BA w/ Water Park, Heated Pool, Arcade, Gym & More
  • LUXURY 6 BED VILLA, PRIVATE POOL/SPA, WINDSOR HILLS, BRAND NEW WATER PARK

    LUXURY 6 BED VILLA, PRIVATE POOL/SPA, WINDSOR HILLS, BRAND NEW WATER PARK

    5/5 Excellent
    Awesome stay
    "Our Family absolutely loved staying here this week we definitely used the private pool a lot and we loved that everything was spread out and clean when we arrived we will most definitely be renting again"
    A verified traveler stayed at LUXURY 6 BED VILLA, PRIVATE POOL/SPA, WINDSOR HILLS, BRAND NEW WATER PARK
    Posted 2 months ago
    LUXURY 6 BED VILLA, PRIVATE POOL/SPA, WINDSOR HILLS, BRAND NEW WATER PARK
  • 🌟Beautiful Private End Unit Townhome Close To Clubhouse🌟

    🌟Beautiful Private End Unit Townhome Close To Clubhouse🌟

    5/5 Excellent
    You Need To Stay Here!
    "Where to begin? We loved everything about this townhouse: Very CLEAN (that was really appreciated), fantastic location relative to all 4 Parks (it was only a 10-12 minute drive each way), the pool at this unit was so nice and refreshing after a long day at the Parks, there was more than enough space for the 6 of us, and the owners Kevin and Jeannie were so accommodating and easy to communicate with. Not only would I recommend this Townhouse to someone else, I will definitely stay at this property again."
    A verified traveler stayed at 🌟Beautiful Private End Unit Townhome Close To Clubhouse🌟
    Posted 2 months ago
    🌟Beautiful Private End Unit Townhome Close To Clubhouse🌟

Explore a world of travel with Expedia

See our travel options