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Our top choices for Windward Cay hotels

Exterior
La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North
3.0 star property
22.8 km from Windward Cay
7.4 out of 10, Good, (878)
"nice and clean staff was great also"
United States
sumatran
The price is 2.295.453 ₫
2.582.384 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
La Quinta Inn & Suites by Wyndham Orlando Airport North
Exterior
Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
3.0 star property
22.8 km from Windward Cay
9.4 out of 10, Exceptional, (2456)
"Great stay "
United States
Nancy
The price is 2.568.696 ₫
2.889.782 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hampton Inn & Suites Orlando Airport @ Gateway Village
Restaurant
Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport
3.0 star property
23.5 km from Windward Cay
8.8 out of 10, Excellent, (3720)
"Beautiful property, excellent staff and love the shuttle service to the airport!"
United States
Robert
The price is 2.392.852 ₫
2.691.629 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Wingate by Wyndham - Orlando International Airport
Reception
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
8.8 out of 10, Excellent, (3297)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is 2.132.244 ₫
2.420.098 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
Seasons Florida Resort
Terrace/patio
Hyatt House Orlando Airport

Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
22.7 km from Windward Cay
9.6 out of 10, Exceptional, (2806)
"Great location, friendly staff, great breakfast"
United States
Gabriel
The price is 3.395.796 ₫
3.820.402 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hyatt House Orlando Airport
Outdoor banquet area
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
13.4 km from Windward Cay
9.4 out of 10, Exceptional, (4365)
"Amazing place"
United States
Joseph
The price is 2.927.229 ₫
3.293.133 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Rosen Shingle Creek
Exterior
avid hotel Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG
2.5 star property
21.2 km from Windward Cay
9.2 out of 10, Wonderful, (2018)
"Easy check in, great people service, clean room, great location. "
United States
Tiffany
The price is 2.895.640 ₫
3.257.595 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
avid hotel Orlando International Airport by IHG
Courtyard
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando
4.0 star property
18.8 km from Windward Cay
8.4 out of 10, Very good, (6887)
"Wonderful stay. Great location!"
United States
Charmaine
The price is 2.568.696 ₫
2.889.784 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
DoubleTree by Hilton at the Entrance to Universal Orlando
Lobby
Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
21.1 km from Windward Cay
8.8 out of 10, Excellent, (1931)
"Clean room and pleasant staff. "
United States
Mariama Velinique
The price is 2.395.491 ₫
2.694.927 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Cambria Hotel Orlando Airport
Studio Suite, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Accessible) | Premium bedding, in-room safe, desk, blackout curtains
Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport
3.0 star property
23 km from Windward Cay
8.2 out of 10, Very good, (5208)
"Excellent place"
United States
Leonard
The price is 2.595.546 ₫
2.919.989 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Ramada by Wyndham Suites Orlando Airport
Property amenity
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
3.0 star property
9.6 km from Windward Cay
8.6 out of 10, Excellent, (3475)
"Wonderful staff and great location and clean room"
United States
farrah a
The price is 2.290.188 ₫
2.576.462 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
Free daily buffet breakfast
Hampton Inn Orlando-International Airport

Hampton Inn Orlando-International Airport

Hampton Inn Orlando-International Airport
2.5 star property
23.3 km from Windward Cay
9.0 out of 10, Wonderful, (1737)
"clean room, great location for restaurants and taking walks around the small lake."
United States
Walter
The price is 2.352.839 ₫
2.646.944 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn Orlando-International Airport
Exterior
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway
3.0 star property
11.4 km from Windward Cay
8.0 out of 10, Very good, (3898)
"Always great to stay there "
United States
Giandre
The price is 1.326.730 ₫
2.043.638 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Ramada by Wyndham Kissimmee Gateway
View from room
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista
3.5 star property
8.9 km from Windward Cay
8.6 out of 10, Excellent, (5642)
"Great property to stay"
United States
Deepankar
The price is 2.345.205 ₫
2.638.356 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Rosen Inn Lake Buena Vista
Lobby
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
17.1 km from Windward Cay
9.4 out of 10, Exceptional, (1378)
"The staff was really friendly and the property was nice and cozy "
United States
curtis
The price is 3.106.232 ₫
3.494.511 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt House Orlando International Drive
Exterior
Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Express Orlando International Airport by IHG
2.5 star property
20.9 km from Windward Cay
9.0 out of 10, Wonderful, (1881)
" Nice hotel"
United States
Shalanda
The price is 2.711.372 ₫
3.050.294 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Holiday Inn Express Orlando International Airport by IHG
Exterior
Caribe Royale Orlando

Caribe Royale Orlando

Caribe Royale Orlando
4.5 star property
5.6 km from Windward Cay
9.2 out of 10, Wonderful, (4508)
"Excellent hotel I will be booking again"
United States
Wilshaundra
The price is 4.185.516 ₫
5.834.056 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Caribe Royale Orlando
Business centre
Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
19.7 km from Windward Cay
9.0 out of 10, Wonderful, (451)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is 2.282.028 ₫
2.567.282 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Spark by Hilton Orlando near Universal
2 restaurants, breakfast, lunch, dinner served; Mexican cuisine
Red Lion Hotel Orlando Lake Buena Vista South

Red Lion Hotel Orlando Lake Buena Vista South

Red Lion Hotel Orlando Lake Buena Vista South
3.5 star property
3 km from Windward Cay
8.8 out of 10, Excellent, (4265)
"Beautiful place to stay, reliable price, the location was perfect, super clean, definitely I will return back in a future to this hotel."
United States
Aurelis
The price is 1.790.032 ₫
2.629.241 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Red Lion Hotel Orlando Lake Buena Vista South
Premium bedding, down duvets, in-room safe, desk
Comfort Suites Orlando Airport

Comfort Suites Orlando Airport

Comfort Suites Orlando Airport
2.5 star property
19.5 km from Windward Cay
8.4 out of 10, Very good, (1396)
"This is one of my favorite hotels,it’s clean workers are very friendly,I’ll recommend anyone there "
United States
Marlene
The price is 2.526.841 ₫
2.842.696 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Comfort Suites Orlando Airport
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.
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Where to stay in Windward Cay

Find the best Windward Cay areas for the activities you enjoy most.

International Drive District

Visitors to International Drive District rave about its breathtaking beach views, exciting theme parks and popular shops. You might also want to make some time to see Pointe Orlando or Aquatica while you're exploring the neighbourhood.

Magic Kingdom® Theme Park showing interior views and rides as well as a couple
Photo by ©Disney
Open Photo by ©Disney

Bay Lake

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

Champions Gate

Ample dining options and top golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

Universal Studios Florida® featuring night scenes, a city and signage

Florida Center

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

Downtown Orlando

Ample dining options, great live music, and fantastic lake views are just a few top things to explore in Downtown Orlando. A visit to The Social or Orlando City Hall might round out your trip, and you can jump aboard the metro at Church Street Station or Lynx Central Station to get around town.

Top Windward Cay Hotel Reviews

Frequently asked questions

What's it like in Windward Cay?
Travellers to the Windward Cay neighbourhood in Kissimmee will be sure to enjoy their stay.
How many hotels will I be able to find in Windward Cay?
Expedia has 28 hotels and other accommodation options in Windward Cay to choose from, making this an ideal home base for exploring the greater Kissimmee area.
If I need to cancel my hotel reservation in Windward Cay, will I receive a refund?
Yes! The majority of hotel reservations are fully refundable if you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Put your dates in and click on "Search", then you can filter by "fully refundable" to review the best options available in Windward Cay.
What is there to do around this Kissimmee neighbourhood?
A few places to visit in the area around Windward Cay include Old Town, Medieval Times and Kissimmee Go-Karts. While you're out sightseeing, Capone's Dinner Show and Pirate's Island Adventure Golf are a couple of additional sights to visit in Kissimmee.