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 32 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

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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

Nick

NT$4,168 total

includes taxes & fees

Aug 30 - Aug 31

2. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

John

NT$7,503 total

includes taxes & fees

Aug 14 - Aug 15

3. Seasons Florida Resort

1.6 km from Windward Cay

Joel

NT$1,945 total

includes taxes & fees

Aug 18 - Aug 19

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

4. Buena Vista Suites Orlando

5.7 km from Windward Cay

Marquez

NT$4,944 total

includes taxes & fees

Aug 12 - Aug 13

5. Hyatt Regency Orlando International Airport

21.3 km from Windward Cay

Tracy

NT$6,869 total

includes taxes & fees

Sep 2 - Sep 3

6. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Kayanna

NT$5,083 total

includes taxes & fees

Aug 30 - Aug 31

Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)

7. Meliá Orlando Celebration

6.8 km from Windward Cay

Roxana

NT$4,233 total

includes taxes & fees

Aug 21 - Aug 22

In-room safe, laptop workspace, blackout drapes, iron/ironing board

8. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Jose

NT$1,885 total

includes taxes & fees

Aug 12 - Aug 13

9. Home2 Suites by Hilton Orlando at Flamingo Crossings

16.2 km from Windward Cay

Kelly

NT$3,006 total

includes taxes & fees

Aug 23 - Aug 24

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

9.5 km from Windward Cay

Ana E

NT$2,863 total

includes taxes & fees

Aug 12 - Aug 13

11. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

Soraida

NT$2,348 total

includes taxes & fees

Aug 31 - Sep 1

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

9.5 km from Windward Cay

Tracey

NT$3,008 total

includes taxes & fees

Sep 9 - Sep 10

13. Hyatt House Orlando Airport

22.7 km from Windward Cay

Osvaldo

NT$3,987 total

includes taxes & fees

Aug 18 - Aug 19

14. Hampton Inn & Suites Orlando Airport @ Gateway Village

22.8 km from Windward Cay

Ianna

NT$3,388 total

includes taxes & fees

Aug 17 - Aug 18

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

9.8 km from Windward Cay

Susanna

NT$3,230 total

includes taxes & fees

Aug 17 - Aug 18

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

3.2 km from Windward Cay

Alexander

NT$2,178 total

includes taxes & fees

Aug 12 - Aug 13

17. Wyndham Garden Orlando Airport

19.9 km from Windward Cay

Gabriel

NT$3,574 total

includes taxes & fees

Aug 12 - Aug 13

18. Star Island Resort and Club

2.4 km from Windward Cay

Caroline

NT$3,932 total

includes taxes & fees

Aug 15 - Aug 16

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

9 km from Windward Cay

Steven

NT$2,700 total

includes taxes & fees

Aug 20 - Aug 21

20. The Vietta Hotel

2.6 km from Windward Cay

Andrea

NT$2,811 total

includes taxes & fees

Aug 13 - Aug 14

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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

Lake Buena Vista Resort Village & Spa

10/10 Excellent

"Todo perfecto"

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"hotel it self was wonderful everything u need is right there. however the darn toilet would not flush kept clogging. keep in mind we was there for about 4 nights. ice cream area could use a makeover. but loved this place would come back when in orlando"

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Our top choices for Windward Cay hotels

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

2. Caribe Royale Orlando, WorldHotels Elite

3. Seasons Florida Resort

4. Buena Vista Suites Orlando

5. Hyatt Regency Orlando International Airport

6. Drury Plaza Hotel Orlando - Disney Springs Area

7. Meliá Orlando Celebration

8. Palazzo Lakeside Hotel

9. Home2 Suites by Hilton Orlando at Flamingo Crossings

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

11. Radisson Hotel Orlando Lake Buena Vista South

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

13. Hyatt House Orlando Airport

14. Hampton Inn & Suites Orlando Airport @ Gateway Village

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

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

17. Wyndham Garden Orlando Airport

18. Star Island Resort and Club

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

20. The Vietta Hotel

Where to stay in Windward Cay

Bay Lake

International Drive District

Reunion

Florida Center

Champions Gate

Top Windward Cay Hotel Reviews

Lake Buena Vista Resort Village & Spa

Frequently asked questions

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