A golf course with a large hotel and residential area.

Windward Cay Hotels, Orlando

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Windward Cay hotels

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
3 km from Windward Cay
9.6 out of 10, Exceptional, (1,585 reviews)
"Rooms were clean and breakfast was good."
United States
Cassandra
The price is NZ$180
includes taxes & fees
18 Oct - 19 Oct
Embassy Suites by Hilton Orlando Lake Buena Vista South
A hotel with a central entrance, palm trees, and a clear sky.

2. Comfort Suites Maingate East

Comfort Suites Maingate East
3.0 star property
4.6 km from Windward Cay
8.4 out of 10, Very good, (2,571 reviews)
"All the accommodations near the hotel was a plus"
United States
Diahiana
The price is NZ$143
includes taxes & fees
20 Oct - 21 Oct
Comfort Suites Maingate East
A modern waiting area with two black chairs, a small table with a plant, and a large window offering a view of trees and buildings.

3. Travelodge by Wyndham Orlando Lake Buena Vista South

Travelodge by Wyndham Orlando Lake Buena Vista South
2.0 star property
3.6 km from Windward Cay
7.6 out of 10, Good, (1,007 reviews)
"It was okay! Great price and good breakfast"
United States
Paola
The price is NZ$112
includes taxes & fees
14 Oct - 15 Oct
Travelodge by Wyndham Orlando Lake Buena Vista South
A swimming pool with a blue slide, surrounded by palm trees and a fenced area.

4. Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
3 km from Windward Cay
8.8 out of 10, Excellent, (3,816 reviews)
"Great place to stay and close to everything. Love the lazy river and the fact there is a Mexican restaurant in the lobby."
United States
Angela
The price is NZ$127
includes taxes & fees
8 Oct - 9 Oct
Radisson Hotel Orlando Lake Buena Vista South
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

5. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
9.0 out of 10, Wonderful, (3,971 reviews)
"Exellent place to stay!!"
United States
Antonio
The price is NZ$72
includes taxes & fees
14 Oct - 15 Oct
Seasons Florida Resort
A hotel room with a large bed, a smaller bed, a desk, and a chair. There is a decorative item on the bed and a rug on the floor.

6. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.4 out of 10, Very good, (5,326 reviews)
"Great stay for a great price"
United States
Joel
The price is NZ$111
includes taxes & fees
1 Oct - 2 Oct
Palazzo Lakeside Hotel
A modern living room with a large flat-screen TV, a white sofa, and a coffee table.

7. Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
3.0 star property
3.2 km from Windward Cay
8.6 out of 10, Excellent, (3,231 reviews)
"Great place to stay!!"
United States
Mirtha
The price is NZ$158
includes taxes & fees
1 Oct - 2 Oct
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
A modern reception desk with a wooden finish and the logo 'THE VIETTA'.

8. The Vietta Hotel

The Vietta Hotel
2.0 star property
2.6 km from Windward Cay
7.8 out of 10, Good, (1,000 reviews)
"European style hotel, like it very much . Stay there all the time when I visiting Orlando area. Recommend"
United States
Norris
The price is NZ$149
includes taxes & fees
19 Oct - 20 Oct
The Vietta Hotel
A swimming pool with people in the water, including a person in a green and red inflatable ring.

9. Buena Vista Suites Orlando

Buena Vista Suites Orlando
4.0 star property
5.7 km from Windward Cay
9.2 out of 10, Wonderful, (2,567 reviews)
"Great hotel"
United States
Laura
The price is NZ$280
includes taxes & fees
1 Oct - 2 Oct
Buena Vista Suites Orlando
A spacious lobby with a high ceiling, wooden beams, and a central round table surrounded by chairs. There are potted plants, a reception desk, and a wall with a welcome sign.

10. Hilton Vacation Club Polynesian Isles Kissimmee

Hilton Vacation Club Polynesian Isles Kissimmee
3.0 star property
3.9 km from Windward Cay
9.6 out of 10, Exceptional, (1,916 reviews)
"Amazing staff and amazing property. Staff was absolutely amazing. Room was beautiful and very clean"
United States
Megan
The price is NZ$232
includes taxes & fees
5 Oct - 6 Oct
Hilton Vacation Club Polynesian Isles Kissimmee
An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.

11. Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
6.8 km from Windward Cay
8.8 out of 10, Excellent, (1,627 reviews)
"Great place to stay"
United States
Juanita
The price is NZ$178
includes taxes & fees
7 Oct - 8 Oct
Meliá Orlando Celebration
A multi-story hotel with a swimming pool, parking, and a landscaped area.

12. Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
3.0 star property
9.5 km from Windward Cay
8.8 out of 10, Excellent, (2,345 reviews)
"Very great place!!!"
United States
Abi Carolina Fornino
The price is NZ$158
includes taxes & fees
1 Oct - 2 Oct
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
A hotel with a large pool, palm trees, and a waterfall feature.

13. Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite
4.5 star property
5.7 km from Windward Cay
9.2 out of 10, Wonderful, (5,324 reviews)
"We stay here all the time and love it!"
United States
Brittany
The price is NZ$453
includes taxes & fees
3 Oct - 4 Oct
Caribe Royale Orlando, WorldHotels Elite
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

14. 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, (6,094 reviews)
"Very peaceful and convinient stay, close to where we where headed and not loud environment"
United States
Odett
The price is NZ$120
includes taxes & fees
27 Oct - 28 Oct
Rosen Inn Lake Buena Vista
An arcade with various gaming machines, including racing and motorcycle games.

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

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
7.6 km from Windward Cay
8.6 out of 10, Excellent, (4,021 reviews)
"It was a great stay!"
United States
Rosalinda
The price is NZ$206
includes taxes & fees
1 Oct - 2 Oct
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
A modern hotel with a prominent 'SPOT HOTEL' sign, a curved entrance, and a number '12235' displayed on the facade.

16. SPOT X Hotel Orlando/Intl Dr by The Red Collection

SPOT X Hotel Orlando/Intl Dr by The Red Collection
3.0 star property
9 km from Windward Cay
8.6 out of 10, Excellent, (3,709 reviews)
"We loved this hotel Central to everything we needed and the staff were awesome Highly recommend"
Canada
Lisa
The price is NZ$139
includes taxes & fees
26 Oct - 27 Oct
SPOT X Hotel Orlando/Intl Dr by The Red Collection
A reception desk area with a neon sign reading "TRYP Orlando" and a modern wooden ceiling.

17. TRYP by Wyndham Orlando

TRYP by Wyndham Orlando
3.0 star property
9.9 km from Windward Cay
9.0 out of 10, Wonderful, (1,492 reviews)
"The staff was wonderful."
United States
Regina
The price is NZ$169
includes taxes & fees
1 Oct - 2 Oct
TRYP by Wyndham Orlando
A modern hotel with "La Quinta" signage, featuring a prominent entrance and a covered outdoor area.

18. La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
3.0 star property
9.8 km from Windward Cay
8.8 out of 10, Excellent, (3,128 reviews)
"The facilities are perfect, the room was amazing, the staff very gentle, the breakfast delicious."
United States
Jessica
The price is NZ$172
includes taxes & fees
5 Oct - 6 Oct
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
A modern indoor patio with a fire pit table, seating, a bar area, and large windows.

19. SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
3.0 star property
9.5 km from Windward Cay
8.8 out of 10, Excellent, (3,618 reviews)
"Clean rooms very nice staff the breakfast was very good delicious"
United States
Maria
The price is NZ$174
includes taxes & fees
28 Oct - 29 Oct
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

20. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
6.5 km from Windward Cay
8.6 out of 10, Excellent, (5,099 reviews)
"Great place"
United States
Wilbert
The price is NZ$181
includes taxes & fees
25 Oct - 26 Oct
Vacation Village Orlando, Celebration
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

Our guide on 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 a blue light, surrounded by a water fountain display and palm trees.

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.

Orlando downtown welcome sign with tropical scene; Shutterstock ID 99801884

Downtown Orlando

One of the most popular neighborhoods in Florida, this bustling area is full of art galleries, shops, bars and restaurants.

Top Windward Cay Hotel Reviews

Recent Reviews in Windward Cay

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Breakfast was mobbed but I guess that's a sign of good food. Great pool and lazy river. My 4 year old loved it!!"
Douglas 2-night trip
Posted 8 hours ago
Kompose Boutique Resort at Theme Parks

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.