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

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

3 km from Windward Cay

Ivandra

NT$3,229 total

includes taxes & fees

Oct 4 - Oct 5

2. Buena Vista Suites Orlando

5.7 km from Windward Cay

Jose

NT$5,589 total

includes taxes & fees

Sep 8 - Sep 9

3. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Lyann

NT$7,546 total

includes taxes & fees

Sep 8 - Sep 9

4. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

yesenia

NT$2,306 total

includes taxes & fees

Sep 28 - Sep 29

5. Seasons Florida Resort

1.6 km from Windward Cay

Joel

NT$1,873 total

includes taxes & fees

Sep 9 - Sep 10

6. Hyatt Regency Orlando International Airport

21.3 km from Windward Cay

Debbie

NT$7,439 total

includes taxes & fees

Sep 8 - Sep 9

7. Hyatt House Orlando Airport

22.7 km from Windward Cay

suketu

NT$3,915 total

includes taxes & fees

Sep 20 - Sep 21

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

9.5 km from Windward Cay

Shander Aria

NT$3,010 total

includes taxes & fees

Sep 9 - Sep 10

9. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Samantha

NT$4,992 total

includes taxes & fees

Sep 21 - Sep 22

10. Palazzo Lakeside Hotel

2.7 km from Windward Cay

LILLIAN

NT$2,100 total

includes taxes & fees

Sep 9 - Sep 10

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

9.5 km from Windward Cay

Caitlin

NT$2,812 total

includes taxes & fees

Sep 10 - Sep 11

12. Home2 Suites by Hilton Orlando at Flamingo Crossings

16.2 km from Windward Cay

Wilfred

NT$3,211 total

includes taxes & fees

Sep 28 - Sep 29

13. AC Hotel by Marriott Orlando Lake Buena Vista

8.4 km from Windward Cay

Rocio Del mar

NT$3,524 total

includes taxes & fees

Sep 8 - Sep 9

14. Meliá Orlando Celebration

6.8 km from Windward Cay

Juanita

NT$3,379 total

includes taxes & fees

Sep 17 - Sep 18

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

3.2 km from Windward Cay

Jose

NT$2,133 total

includes taxes & fees

Sep 8 - Sep 9

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

9.8 km from Windward Cay

Stephanie

NT$3,268 total

includes taxes & fees

Sep 8 - Sep 9

17. Rosen Shingle Creek

13.4 km from Windward Cay

Mariana

NT$4,243 total

includes taxes & fees

Sep 8 - Sep 9

18. Wyndham Garden Orlando Airport

19.9 km from Windward Cay

Gabriel

NT$3,177 total

includes taxes & fees

Sep 8 - Sep 9

19. Hampton Inn & Suites Orlando Airport @ Gateway Village

22.8 km from Windward Cay

Stacy

NT$3,184 total

includes taxes & fees

Sep 13 - Sep 14

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

16.4 km from Windward Cay

Lauren

NT$3,915 total

includes taxes & fees

Sep 14 - Sep 15

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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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Top Windward Cay Hotel Reviews

The Grove Resort & Water Park Orlando

10/10 Excellent

"Everything was amazing"

Rosen Inn Lake Buena Vista

10/10 Excellent

"We always stay at the Rosen and have been coming here for about 8–9 years. The staff is always wonderful, friendly, and welcoming. The only thing I’m disappointed about is the parking fee, it used to be free. If we’re already staying at the hotel and paying for our rooms, I don’t understand why we should also have to pay for parking. I know many hotels are doing this now, but I think it’s a ripoff for guests in general. Other than that, we love this hotel and always enjoy our stay."

Find hotels in Windward Cay, Orlando

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Our top choices for Windward Cay hotels

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

2. Buena Vista Suites Orlando

3. Caribe Royale Orlando, WorldHotels Elite

4. Radisson Hotel Orlando Lake Buena Vista South

5. Seasons Florida Resort

6. Hyatt Regency Orlando International Airport

7. Hyatt House Orlando Airport

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

9. Drury Plaza Hotel Orlando - Disney Springs Area

10. Palazzo Lakeside Hotel

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

12. Home2 Suites by Hilton Orlando at Flamingo Crossings

13. AC Hotel by Marriott Orlando Lake Buena Vista

14. Meliá Orlando Celebration

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

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

17. Rosen Shingle Creek

18. Wyndham Garden Orlando Airport

19. Hampton Inn & Suites Orlando Airport @ Gateway Village

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

Where to stay in Windward Cay

Bay Lake

International Drive District

Reunion

Florida Center

Champions Gate

Top Windward Cay Hotel Reviews

The Grove Resort & Water Park Orlando

Frequently asked questions

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