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

Ivandra

includes taxes & fees

4 Oct - 5 Oct

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

2. Seasons Florida Resort

1.6 km from Windward Cay

Joel

includes taxes & fees

9 Sept - 10 Sept

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

2.7 km from Windward Cay

LILLIAN

includes taxes & fees

9 Sept - 10 Sept

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

3.2 km from Windward Cay

Jose

includes taxes & fees

30 Sept - 1 Oct

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

5. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

yesenia

includes taxes & fees

28 Sept - 29 Sept

6. The Vietta Hotel

2.6 km from Windward Cay

Fakhar-ud-din

includes taxes & fees

8 Sept - 9 Sept

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.

7. Hilton Vacation Club Polynesian Isles Kissimmee

3.9 km from Windward Cay

MAHADEVAN

includes taxes & fees

8 Sept - 9 Sept

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

8. Meliá Orlando Celebration

6.8 km from Windward Cay

Juanita

includes taxes & fees

17 Sept - 18 Sept

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

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

9.5 km from Windward Cay

Shander Aria

includes taxes & fees

9 Sept - 10 Sept

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

10. Buena Vista Suites Orlando

5.7 km from Windward Cay

Jose

includes taxes & fees

8 Sept - 9 Sept

A large outdoor swimming pool with multiple lanes, surrounded by lounge chairs and umbrellas.

11. Wyndham Lake Buena Vista – Disney Springs® Area

8.2 km from Windward Cay

tracy

includes taxes & fees

8 Sept - 9 Sept

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

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

8.2 km from Windward Cay

Samon

includes taxes & fees

8 Sept - 9 Sept

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

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

9.5 km from Windward Cay

Caitlin

includes taxes & fees

13 Sept - 14 Sept

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

14. AC Hotel by Marriott Orlando Lake Buena Vista

8.4 km from Windward Cay

Rocio Del mar

includes taxes & fees

8 Sept - 9 Sept

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

15. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Samantha

includes taxes & fees

21 Sept - 22 Sept

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

16. Rosen Shingle Creek

13.4 km from Windward Cay

Mariana

includes taxes & fees

8 Sept - 9 Sept

A hotel reception area with a marble counter, a Mickey Mouse decoration, and surfboards on the wall.

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

7.6 km from Windward Cay

juan

includes taxes & fees

10 Sept - 11 Sept

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

9.8 km from Windward Cay

Stephanie

includes taxes & fees

8 Sept - 9 Sept

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

19. Hilton Vacation Club Grand Beach Orlando

6.3 km from Windward Cay

Luis

includes taxes & fees

14 Sept - 15 Sept

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

20. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Lyann

includes taxes & fees

8 Sept - 9 Sept

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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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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.

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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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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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