The Best Hotels in Windward Cay, Orlando - 2026 Updated Prices

Aerial panoramic view of Celebration, Florida, USA. December 3, 2025.

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

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Windward Cay hotels

A hotel with a large pool, palm trees, and a waterfall feature.

1. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Suzette M

฿7,608 total

includes taxes & fees

26 Aug - 27 Aug

A swimming pool with people in the water, including a person in a green and red inflatable ring.

2. Buena Vista Suites Orlando

5.7 km from Windward Cay

Alicia

฿4,947 total

includes taxes & fees

23 Aug - 24 Aug

A hotel atrium with a central fountain, palm trees, and a circular seating area.

3. Hyatt Regency Orlando International Airport

21.3 km from Windward Cay

William

฿6,579 total

includes taxes & fees

7 Sept - 8 Sept

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

4. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Mohammed

฿5,154 total

includes taxes & fees

30 Aug - 31 Aug

A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

5. Seasons Florida Resort

1.6 km from Windward Cay

Joel

฿1,973 total

includes taxes & fees

30 Aug - 31 Aug

An outdoor patio area with seating, a bar, and a fire feature.

6. Hyatt House Orlando Airport

22.7 km from Windward Cay

Suzanne

฿4,043 total

includes taxes & fees

31 Aug - 1 Sept

A modern indoor patio with a fire pit table, seating, a bar area, and large windows.

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

9.5 km from Windward Cay

Mahnoor

฿2,977 total

includes taxes & fees

27 Aug - 28 Aug

A swimming pool with a blue slide, surrounded by palm trees and a fenced area.

8. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

Soraida

฿2,314 total

includes taxes & fees

14 Sept - 15 Sept

A multi-story hotel with a swimming pool, parking, and a landscaped area.

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

9.5 km from Windward Cay

Ana E

฿2,904 total

includes taxes & fees

26 Aug - 27 Aug

A swimming pool surrounded by lounge chairs and umbrellas, with a multi-story building in the background.

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

7.6 km from Windward Cay

gloria

฿3,418 total

includes taxes & fees

26 Aug - 27 Aug

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.

11. Palazzo Lakeside Hotel

2.7 km from Windward Cay

LILLIAN

฿2,127 total

includes taxes & fees

23 Aug - 24 Aug

A modern kitchen with a central island, built-in shelves, and a variety of appliances and utensils.

12. AC Hotel by Marriott Orlando Lake Buena Vista

8.4 km from Windward Cay

Alessandra

฿3,639 total

includes taxes & fees

23 Aug - 24 Aug

An outdoor seating area with green chairs and umbrellas, a fire pit, and a building with large windows in the background.

13. Hampton Inn & Suites Orlando Airport @ Gateway Village

22.8 km from Windward Cay

andrea

฿3,285 total

includes taxes & fees

31 Aug - 1 Sept

A modern hotel lobby with a large flat-screen TV, a blue sofa, a round wooden table, and a curved reception desk.

14. Cambria Hotel Orlando Airport

21.1 km from Windward Cay

Juan

฿3,440 total

includes taxes & fees

23 Aug - 24 Aug

A modern hotel with "La Quinta" signage, featuring a prominent entrance and a covered outdoor area.

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

9.8 km from Windward Cay

Christine

฿3,275 total

includes taxes & fees

24 Aug - 25 Aug

An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

16. Home2 Suites by Hilton Orlando at Flamingo Crossings

16.2 km from Windward Cay

Alicia

฿3,436 total

includes taxes & fees

31 Aug - 1 Sept

An aerial view of a resort with multiple swimming pools, landscaped gardens, and outdoor seating areas.

17. Rosen Shingle Creek

13.4 km from Windward Cay

Mariana

฿4,381 total

includes taxes & fees

6 Sept - 7 Sept

An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

18. Wyndham Grand Orlando Resort Bonnet Creek

8.1 km from Windward Cay

Ian

฿6,101 total

includes taxes & fees

28 Aug - 29 Aug

A multi-story hotel with a modern design, featuring a central atrium with a blue and red accent wall, and a flat roof with green trim.

19. Holiday Inn Express & Suites Orlando at SeaWorld by IHG

11.3 km from Windward Cay

Rob

฿3,124 total

includes taxes & fees

20 Sept - 21 Sept

A modern living room with a large flat-screen TV, a white sofa, and a coffee table.

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

3.2 km from Windward Cay

Owen

฿2,032 total

includes taxes & fees

30 Aug - 31 Aug

View all properties

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.

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.

See properties

The entrance to Aquatica with colorful signage and a water slide.

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.

See properties

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.

See properties

A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.

Florida Center

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

See properties

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.

See properties

Top Windward Cay Hotel Reviews

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"Every thing was great , food the place the pool was perfect I will recommend this place with a 10/10"

DoubleTree by Hilton at the Entrance to Universal Orlando

8/10 Good

"Great location right across the street from Universal Studios. The Hotel guest services were friendly and nice. The house keeping changed the sheets daily and ensured the room had toilet paper. The room door had a little issue with opening and closing and getting in the room with the Hotel key card. When I checked in I shared about the issue with the door and they sent someone to look at it. The pool was nice, however my niece got a big cut on her feet from something sharp in the pool. I would recommend that the Hotel service the pool daily and check for sharp objects before anyone is allowed in the pool. Good stay, however this hotel could use an upgrade. If you have a rental you will be paying for the parking daily. And on one of the days as I was entering the hotel parting, the pole that goes up to let you in went up and then went right back down and almost hit my rental. I was grateful to get through safely."

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 32 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Windward Cay on Expedia.com

Search Hotels in Windward Cay, Orlando

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windward Cay hotels

1. Caribe Royale Orlando, WorldHotels Elite

2. Buena Vista Suites Orlando

3. Hyatt Regency Orlando International Airport

4. Drury Plaza Hotel Orlando - Disney Springs Area

5. Seasons Florida Resort

6. Hyatt House Orlando Airport

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

8. Radisson Hotel Orlando Lake Buena Vista South

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

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

11. Palazzo Lakeside Hotel

12. AC Hotel by Marriott Orlando Lake Buena Vista

13. Hampton Inn & Suites Orlando Airport @ Gateway Village

14. Cambria Hotel Orlando Airport

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

16. Home2 Suites by Hilton Orlando at Flamingo Crossings

17. Rosen Shingle Creek

18. Wyndham Grand Orlando Resort Bonnet Creek

19. Holiday Inn Express & Suites Orlando at SeaWorld by IHG

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

Where to stay in Windward Cay

Bay Lake

International Drive District

Reunion

Florida Center

Champions Gate

Top Windward Cay Hotel Reviews

Kompose Boutique Resort at Theme Parks

Frequently asked questions

Explore a world of travel with Expedia