What's it like in Windward Cay?

Travelers to the Windward Cay neighborhood in Kissimmee will be sure to enjoy their stay.

How many hotels will I find in Windward Cay?

Expedia has 33 hotels and other accommodations 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, most hotel reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best deals available in Windward Cay.

Where can I learn more about changing or cancelling my trip to Windward Cay?

For more information about changing or cancelling your trip to Windward Cay, click here .

What is there to do around this Kissimmee neighborhood?

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.

Top Windward Cay Hotels

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

NT$3,216 total

includes taxes & fees

Oct 4 - Oct 5

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

Jose

NT$5,567 total

includes taxes & fees

Sep 10 - Sep 11

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

3. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Carnesha

NT$7,375 total

includes taxes & fees

Oct 9 - Oct 10

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

Dustin

NT$2,299 total

includes taxes & fees

Sep 29 - Sep 30

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

NT$2,106 total

includes taxes & fees

Sep 23 - Sep 24

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

6. Hyatt Regency Orlando International Airport

21.3 km from Windward Cay

Debbie

NT$7,410 total

includes taxes & fees

Sep 14 - Sep 15

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

7. Hyatt House Orlando Airport

22.7 km from Windward Cay

suketu

NT$3,904 total

includes taxes & fees

Sep 20 - Sep 21

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

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

9.5 km from Windward Cay

Shander Aria

NT$3,017 total

includes taxes & fees

Sep 13 - Sep 14

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

9. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Samantha

NT$4,977 total

includes taxes & fees

Sep 21 - Sep 22

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.

10. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Arcenio

NT$2,113 total

includes taxes & fees

Sep 13 - Sep 14

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

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

9.5 km from Windward Cay

Caitlin

NT$2,804 total

includes taxes & fees

Sep 13 - Sep 14

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

12. Home2 Suites by Hilton Orlando at Flamingo Crossings

16.2 km from Windward Cay

Wilfred

NT$3,201 total

includes taxes & fees

Sep 28 - Sep 29

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

13. AC Hotel by Marriott Orlando Lake Buena Vista

8.4 km from Windward Cay

Rocio Del mar

NT$3,510 total

includes taxes & fees

Sep 13 - Sep 14

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

14. Meliá Orlando Celebration

6.8 km from Windward Cay

Juanita

NT$3,913 total

includes taxes & fees

Sep 16 - Sep 17

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

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

3.2 km from Windward Cay

Teresa

NT$2,151 total

includes taxes & fees

Sep 30 - Oct 1

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

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

9.8 km from Windward Cay

Grace

NT$3,258 total

includes taxes & fees

Sep 14 - Sep 15

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

NT$5,288 total

includes taxes & fees

Sep 12 - Sep 13

A modern gym with treadmills, stationary bikes, and elliptical machines.

18. Wyndham Garden Orlando Airport

19.9 km from Windward Cay

Gabriel

NT$3,165 total

includes taxes & fees

Sep 23 - Sep 24

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

19. Hampton Inn & Suites Orlando Airport @ Gateway Village

22.8 km from Windward Cay

Stacy

NT$3,175 total

includes taxes & fees

Sep 13 - Sep 14

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

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

16.4 km from Windward Cay

Lauren

NT$3,156 total

includes taxes & fees

Sep 27 - Sep 28

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Where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods for the activities you enjoy most.

The entrance to the Hollywood Studios area with a large sign and distinctive architecture.

Bay Lake

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.

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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 waterparks and pristine golf courses 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

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

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A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Abundant dining options and pristine 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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