A golf course with a large hotel and residential area.

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov

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Our top choices for Windward Cay hotels

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.

1. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
4.5 mi from Windward Cay
9.2 out of 10, Wonderful, (7,328 reviews)
"excellent resort"
Canada
Jeremy
The price is £95
includes taxes & fees
15 Dec - 16 Dec
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
A resort pool area with palm trees, lounge chairs, and umbrellas.

2. Marriott's Grande Vista

Marriott's Grande Vista
4.0 star property
6.1 mi from Windward Cay
9.0 out of 10, Wonderful, (5,456 reviews)
"Wonderful stay!"
United States
Christina
The price is £82
includes taxes & fees
10 Dec - 11 Dec
Marriott's Grande Vista
A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

3. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
7.2 mi from Windward Cay
9.4 out of 10, Exceptional, (6,502 reviews)
"Always a great stay"
United States
ivan
The price is £53
includes taxes & fees
17 Nov - 18 Nov
Kompose Boutique Resort at Theme Parks
A resort with a large pool, a water slide, and multiple buildings with balconies.

4. Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area
4.0 star property
8.3 mi from Windward Cay
8.4 out of 10, Very good, (7,325 reviews)
"Me and my family love everything about this place nice and very clean also have a water park for the kids we will be booking here again on our next vacation 😃"
United States
Stacy
The price is £99
includes taxes & fees
2 Dec - 3 Dec
Westgate Lakes Resort & Spa Universal Studios Area
A swimming pool area with multiple water slides and palm trees.

5. Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
3.5 star property
10.9 mi from Windward Cay
9.0 out of 10, Wonderful, (7,868 reviews)
"I love this hotel, it feels like you are in a resort and the location is nice"
United States
aram
The price is £128
includes taxes & fees
14 Dec - 15 Dec
Universal's Cabana Bay Beach Resort
A resort pool with a central water feature, surrounded by palm trees and lounge chairs.

6. Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
4.0 star property
5.4 mi from Windward Cay
9.2 out of 10, Wonderful, (4,280 reviews)
"loved everything about the stay!"
United States
yoselin
The price is £82
includes taxes & fees
13 Dec - 14 Dec
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

7. Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite
4.5 star property
3.6 mi from Windward Cay
9.2 out of 10, Wonderful, (5,331 reviews)
"Perfect family resort."
United States
Omid
The price is £180
includes taxes & fees
22 Nov - 23 Nov
Caribe Royale Orlando, WorldHotels Elite
A water park with multiple slides and water features, surrounded by a multi-story building with balconies.

8. Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG
3.5 star property
4 mi from Windward Cay
7.6 out of 10, Good, (1,273 reviews)
"Good place for the kids and families."
United States
Claudia
The price is £130
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Resort Orlando Suites - Waterpark by IHG
A resort with multiple swimming pools, lounge areas, and a view of the sea.

9. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
11.4 mi from Windward Cay
8.2 out of 10, Very good, (10,959 reviews)
"Great place to stay!"
United States
Jessica
The price is £189
includes taxes & fees
7 Dec - 8 Dec
The Grove Resort & Water Park Orlando
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

10. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
4 mi from Windward Cay
8.6 out of 10, Excellent, (5,324 reviews)
"Great stay"
United States
Jonatan
The price is £84
includes taxes & fees
15 Dec - 16 Dec
Vacation Village Orlando, Celebration
A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

11. Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
4.0 star property
5.2 mi from Windward Cay
9.8 out of 10, Exceptional, (6,252 reviews)
"One of the best hotels in the area"
United States
Alan
The price is £158
includes taxes & fees
23 Nov - 24 Nov
Drury Plaza Hotel Orlando - Disney Springs Area
A resort with a large pool, a water slide, and a beach area.

12. Evermore Orlando Resort

Evermore Orlando Resort
4.0 star property
7.3 mi from Windward Cay
9.6 out of 10, Exceptional, (863 reviews)
"This place was great my family had a great time and were really impressed with the customer service, cleanliness and amount of activities that are available."
United States
Raquel
Evermore Orlando Resort
A resort with multiple swimming pools, a pirate ship-themed water attraction, and lush greenery.

13. Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa
4.0 star property
3.1 mi from Windward Cay
8.4 out of 10, Very good, (10,790 reviews)
"Beautiful resorts we loved it!"
United States
Karina
Lake Buena Vista Resort Village & Spa
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

14. Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
2.0 star property
1 mi from Windward Cay
9.0 out of 10, Wonderful, (4,119 reviews)
"great stay"
United States
Viridiana
The price is £35
includes taxes & fees
19 Nov - 20 Nov
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

15. Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista
3.5 star property
5.5 mi from Windward Cay
8.6 out of 10, Excellent, (6,307 reviews)
"Great for a quick stay over"
United States
Clayton
The price is £55
includes taxes & fees
8 Dec - 9 Dec
Rosen Inn Lake Buena Vista
A large hotel with a distinctive pyramid-shaped building, a central courtyard with palm trees, and a body of water reflecting the structure.

16. Walt Disney World Dolphin

Walt Disney World Dolphin
4.0 star property
6.7 mi from Windward Cay
9.0 out of 10, Wonderful, (4,762 reviews)
"Excellent stay"
United States
Alana
The price is £187
includes taxes & fees
29 Nov - 30 Nov
Walt Disney World Dolphin
A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

17. Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
1.9 mi from Windward Cay
9.6 out of 10, Exceptional, (1,698 reviews)
"Great stay"
United States
Peterjohn
The price is £102
includes taxes & fees
22 Nov - 23 Nov
Embassy Suites by Hilton Orlando Lake Buena Vista South
A modern interior with a white spiral staircase, a large Christmas tree, and a dining area with white furniture.

18. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
1.7 mi from Windward Cay
8.4 out of 10, Very good, (5,395 reviews)
"It was a very good hotel"
United States
Ilse
The price is £44
includes taxes & fees
29 Nov - 30 Nov
Palazzo Lakeside Hotel
A poolside area with lounge chairs and umbrellas, a fire pit, and a pool.

19. Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
4.7 mi from Windward Cay
8.6 out of 10, Excellent, (3,999 reviews)
"I really enjoy staying here friendly staff great for kids"
United States
Jesus
The price is £87
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
A hotel pool area with a water slide, palm trees, and a bridge.

20. Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
1.9 mi from Windward Cay
8.8 out of 10, Excellent, (3,733 reviews)
"Always a pleasure staying there"
United States
Sandra
The price is £57
includes taxes & fees
29 Nov - 30 Nov
Radisson Hotel Orlando Lake Buena Vista South
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.
View all properties

Compare popular hotels in Windward Cay

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A kitchen with wooden cabinets, a microwave, a refrigerator, and two bar stools.
Club Sevilla
3.5 star property
9.0
Wonderful
1,003 reviews
View
A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.
Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
9.6
Exceptional
1,698 reviews
View
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
2.0 star property
9.0
Wonderful
4,119 reviews
View
A modern living room with a large flat-screen TV, a white sofa, and a coffee table.
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
3.0 star property
8.6
Excellent
3,231 reviews
View
A hotel pool area with a water slide, palm trees, and a bridge.
Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
8.8
Excellent
3,733 reviews
View

Where to stay in Windward Cay

Find the best Windward Cay areas for the activities you enjoy most.
The entrance to the Hollywood Studios area with a large sign and distinctive architecture.
Photo by Gary Burke
Open Photo by Gary Burke

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.

A large Ferris wheel with blue lights, surrounded by a cityscape with illuminated buildings and a tall green tower.

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.
Photo by Peter Sutton
Open Photo by Peter Sutton

Florida Center

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

A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

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.

A golf course with bunkers, water hazards, and a large lake.

Reunion

The top golf courses and fun-filled water parks are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Top Windward Cay Hotel Reviews

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Clean room was nice and spacious"
melvin 3-night trip
Posted less than an hour ago
Westgate Lakes Resort & Spa Universal Studios Area

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 33 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, Pioneer Village at Shingle Creek and 192 Flea Market are a couple of additional sights to visit in Kissimmee.