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 swimming pool with a waterfall feature, lounge chairs, and a gazebo.

1. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4.5 mi from Windward Cay

Melissa

includes taxes & fees

27 Oct - 28 Oct

A resort pool area with palm trees, lounge chairs, and umbrellas.

2. Marriott's Grande Vista

6.1 mi from Windward Cay

Andy

includes taxes & fees

27 Oct - 28 Oct

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

3. Kompose Boutique Resort at Theme Parks

7.2 mi from Windward Cay

RAJA

includes taxes & fees

21 Oct - 22 Oct

A resort with a large pool, a water slide, and multiple buildings with balconies.

4. Westgate Lakes Resort & Spa Universal Studios Area

8.3 mi from Windward Cay

Juan

includes taxes & fees

1 Oct - 2 Oct

A resort pool with a central water feature, surrounded by palm trees and lounge chairs.

5. Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

5.4 mi from Windward Cay

Vanessa

includes taxes & fees

26 Oct - 27 Oct

A resort with a large pool, water slides, palm trees, and beach umbrellas.

6. The Grove Resort & Water Park Orlando

11.4 mi from Windward Cay

Shereen

includes taxes & fees

1 Oct - 2 Oct

A water park with multiple slides and water features, surrounded by a multi-story building with balconies.

7. Holiday Inn Resort Orlando Suites - Waterpark by IHG

4 mi from Windward Cay

Maylier

includes taxes & fees

28 Oct - 29 Oct

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

8. Seasons Florida Resort

1 mi from Windward Cay

Antonio

includes taxes & fees

6 Oct - 7 Oct

A swimming pool area with multiple water slides and palm trees.

9. Universal's Cabana Bay Beach Resort

10.9 mi from Windward Cay

Kateya

includes taxes & fees

21 Oct - 22 Oct

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

10. Caribe Royale Orlando, WorldHotels Elite

3.6 mi from Windward Cay

Brittany

includes taxes & fees

3 Oct - 4 Oct

A resort with a large pool, a water slide, and a beach area.

11. Evermore Orlando Resort

7.3 mi from Windward Cay

Annika

A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

12. Vacation Village Orlando, Celebration

4 mi from Windward Cay

Monica

includes taxes & fees

29 Oct - 30 Oct

A resort with multiple swimming pools, a pirate ship-themed water attraction, and lush greenery.

13. Lake Buena Vista Resort Village & Spa

3.1 mi from Windward Cay

Doniyor

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

14. Drury Plaza Hotel Orlando - Disney Springs Area

5.2 mi from Windward Cay

Brianne

includes taxes & fees

13 Oct - 14 Oct

A large hotel with a distinctive pyramid-shaped building, a central courtyard with palm trees, and a body of water reflecting the structure.

15. Walt Disney World Dolphin

6.7 mi from Windward Cay

Stephanie

includes taxes & fees

1 Oct - 2 Oct

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

16. Embassy Suites by Hilton Orlando Lake Buena Vista South

1.9 mi from Windward Cay

Cassandra

includes taxes & fees

25 Oct - 26 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.

17. Palazzo Lakeside Hotel

1.7 mi from Windward Cay

Joel

includes taxes & fees

1 Oct - 2 Oct

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

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

4.7 mi from Windward Cay

Rosalinda

includes taxes & fees

1 Oct - 2 Oct

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

19. Radisson Hotel Orlando Lake Buena Vista South

1.9 mi from Windward Cay

Angela

includes taxes & fees

12 Oct - 13 Oct

A spacious lobby with a high ceiling, wooden beams, and a central fountain.

20. Margaritaville Resort Orlando with H2O Waterpark

8.6 mi from Windward Cay

Mike

includes taxes & fees

21 Oct - 22 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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