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.

Windward Cay Hotels: Cheap Accommodation in Windward Cay

A golf course with a large hotel and residential area.

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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

3 km from Windward Cay

Nguyen

includes taxes & fees

18 Oct - 19 Oct

A hotel with a central entrance, palm trees, and a clear sky.

2. Comfort Suites Maingate East

4.6 km from Windward Cay

Diahiana

includes taxes & fees

2 Nov - 3 Nov

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

3. Seasons Florida Resort

1.6 km from Windward Cay

Antonio

includes taxes & fees

11 Oct - 12 Oct

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

4. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

JORGE

includes taxes & fees

5 Nov - 6 Nov

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.

5. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Darius

includes taxes & fees

12 Oct - 13 Oct

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

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

3.2 km from Windward Cay

Mirtha

includes taxes & fees

20 Oct - 21 Oct

7. The Vietta Hotel

2.6 km from Windward Cay

Fakhar-ud-din

includes taxes & fees

11 Oct - 12 Oct

A spacious lobby with a large chandelier, a reception desk, and a view of the outside through large windows.

8. Star Island Resort and Club

2.4 km from Windward Cay

Shawn

includes taxes & fees

26 Oct - 27 Oct

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

9. Legacy Vacation Resorts - Kissimmee/Orlando

2.8 km from Windward Cay

Crystal

includes taxes & fees

19 Oct - 20 Oct

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

10. Meliá Orlando Celebration

6.8 km from Windward Cay

David

includes taxes & fees

4 Nov - 5 Nov

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

11. Buena Vista Suites Orlando

5.7 km from Windward Cay

Jonathan

includes taxes & fees

25 Oct - 26 Oct

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

12. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Brittany

includes taxes & fees

10 Oct - 11 Oct

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

13. Rosen Shingle Creek

13.4 km from Windward Cay

Maria

includes taxes & fees

18 Oct - 19 Oct

A hotel reception desk with HP computers, a digital display, and a sign for the SPOT HOTEL ORLANDO.

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

9 km from Windward Cay

Lisa

includes taxes & fees

27 Oct - 28 Oct

A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

15. Kompose Boutique Resort at Theme Parks

11.5 km from Windward Cay

Nicolas

includes taxes & fees

12 Oct - 13 Oct

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

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

7.6 km from Windward Cay

Rosalinda

includes taxes & fees

18 Oct - 19 Oct

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

17. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

16.4 km from Windward Cay

Stephen

includes taxes & fees

3 Nov - 4 Nov

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

18. Rosen Inn Lake Buena Vista

8.9 km from Windward Cay

Odett

includes taxes & fees

14 Oct - 15 Oct

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

19. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Brianne

includes taxes & fees

28 Oct - 29 Oct

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

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

9.5 km from Windward Cay

Fabiola

includes taxes & fees

3 Nov - 4 Nov

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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.

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 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.

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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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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.

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