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.

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

A golf course with a large hotel and residential area.

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Our top choices for Windward Cay hotels

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

1. Seasons Florida Resort

1 mi from Windward Cay

Antonio

includes taxes & fees

6 Oct - 7 Oct

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

2. Embassy Suites by Hilton Orlando Lake Buena Vista South

1.9 mi from Windward Cay

Cassandra

includes taxes & fees

18 Oct - 19 Oct

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.

3. Palazzo Lakeside Hotel

1.7 mi from Windward Cay

Joel

includes taxes & fees

30 Sept - 1 Oct

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

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

2 mi from Windward Cay

Mirtha

includes taxes & fees

30 Sept - 1 Oct

5. The Vietta Hotel

1.6 mi from Windward Cay

Norris

includes taxes & fees

11 Oct - 12 Oct

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

6. Radisson Hotel Orlando Lake Buena Vista South

1.9 mi from Windward Cay

Angela

includes taxes & fees

12 Oct - 13 Oct

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.

7. Travelodge by Wyndham Orlando Lake Buena Vista South

2.2 mi from Windward Cay

Paola

includes taxes & fees

4 Oct - 5 Oct

An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.

8. Meliá Orlando Celebration

4.3 mi from Windward Cay

Juanita

includes taxes & fees

7 Oct - 8 Oct

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.

9. Hilton Vacation Club Polynesian Isles Kissimmee

2.4 mi from Windward Cay

Megan

includes taxes & fees

30 Sept - 1 Oct

A swimming pool with a covered seating area and palm trees in the background.

10. Legacy Vacation Resorts - Kissimmee/Orlando

1.7 mi from Windward Cay

Yimarie

includes taxes & fees

19 Oct - 20 Oct

An arcade with various gaming machines, including racing and motorcycle games.

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

4.7 mi from Windward Cay

Rosalinda

includes taxes & fees

1 Oct - 2 Oct

A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

12. Rosen Inn Lake Buena Vista

5.5 mi from Windward Cay

Odett

includes taxes & fees

28 Oct - 29 Oct

A large outdoor swimming pool with multiple water features and lounge areas.

13. Wyndham Garden Lake Buena Vista – Disney Springs® Area

5.1 mi from Windward Cay

vanessa Maria louise

includes taxes & fees

30 Sept - 1 Oct

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

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

6.1 mi from Windward Cay

Jessica

includes taxes & fees

30 Sept - 1 Oct

A modern hotel with a prominent 'SPOT HOTEL' sign, a curved entrance, and a number '12235' displayed on the facade.

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

5.6 mi from Windward Cay

Edna M

includes taxes & fees

26 Oct - 27 Oct

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

16. Buena Vista Suites Orlando

3.6 mi from Windward Cay

Laura

includes taxes & fees

25 Oct - 26 Oct

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

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

5.9 mi from Windward Cay

Abi Carolina Fornino

includes taxes & fees

30 Sept - 1 Oct

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

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

5.9 mi from Windward Cay

Maria

includes taxes & fees

28 Oct - 29 Oct

A hotel with a swimming pool, blue lounge chairs, and palm trees.

19. Hilton Vacation Club Grand Beach Orlando

3.9 mi from Windward Cay

Eric

includes taxes & fees

30 Sept - 1 Oct

A reception desk area with a neon sign reading "TRYP Orlando" and a modern wooden ceiling.

20. TRYP by Wyndham Orlando

6.1 mi from Windward Cay

Regina

includes taxes & fees

30 Sept - 1 Oct

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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.

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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.

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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.

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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.

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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.

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Top Windward Cay Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

8/10 Good

"Excellent sized smaller villa with great amenities. Resort is beautiful with so much to do and is a great location. Would highly recommend"

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"The room was clean and spacious, I love the staff so friendly and helpful and the breakfast and kick back are a great feature of staying there. I love the pool and outside bar area. The fact that you can walk to Disney Springs is a real bonus. No resort fee is definitely a plus."

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"From the moment that I checked in with Pamela, it was great. My boyfriend and I went there for Halloween horror nights and our stay at the doubletree was nothing short of wonderful. The beds were comfortable, everything was clean. And I would definitely come back again. Especially for the delicious cookies! :)"

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent

"Came here to say this hotel was great for my wife and I. The amenities were great. 8 minute drive to magic kingdom. The buffet breakfast was phenomenal! Mini Mickey Mouse head waffles were very good! I will definitely be coming back to this hotel !"

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Our top choices for Windward Cay hotels

1. Seasons Florida Resort

2. Embassy Suites by Hilton Orlando Lake Buena Vista South

3. Palazzo Lakeside Hotel

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

5. The Vietta Hotel

6. Radisson Hotel Orlando Lake Buena Vista South

7. Travelodge by Wyndham Orlando Lake Buena Vista South

8. Meliá Orlando Celebration

9. Hilton Vacation Club Polynesian Isles Kissimmee

10. Legacy Vacation Resorts - Kissimmee/Orlando

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

12. Rosen Inn Lake Buena Vista

13. Wyndham Garden Lake Buena Vista – Disney Springs® Area

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

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

16. Buena Vista Suites Orlando

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

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

19. Hilton Vacation Club Grand Beach Orlando

20. TRYP by Wyndham Orlando

Where to stay in Windward Cay

Bay Lake

International Drive District

Florida Center

Champions Gate

Downtown Orlando

Top Windward Cay Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

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