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$4,172 total

includes taxes & fees

Aug 30 - Aug 31

2. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

John

NT$7,511 total

includes taxes & fees

Aug 14 - Aug 15

3. Seasons Florida Resort

1.6 km from Windward Cay

Joel

NT$1,947 total

includes taxes & fees

Aug 16 - Aug 17

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

Alicia

NT$4,884 total

includes taxes & fees

Aug 20 - Aug 21

5. Hyatt Regency Orlando International Airport

21.3 km from Windward Cay

Tracy

NT$6,866 total

includes taxes & fees

Sep 2 - Sep 3

6. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Kayanna

NT$5,088 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

Carolyn

NT$3,697 total

includes taxes & fees

Sep 13 - Sep 14

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

8. Palazzo Lakeside Hotel

2.7 km from Windward Cay

LILLIAN

NT$1,767 total

includes taxes & fees

Aug 16 - Aug 17

9. Home2 Suites by Hilton Orlando at Flamingo Crossings

16.2 km from Windward Cay

Kelly

NT$2,883 total

includes taxes & fees

Aug 26 - Aug 27

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

9.5 km from Windward Cay

Ana E

NT$2,866 total

includes taxes & fees

Aug 17 - Aug 18

11. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

Soraida

NT$2,350 total

includes taxes & fees

Sep 3 - Sep 4

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

9.5 km from Windward Cay

Mahnoor

NT$3,556 total

includes taxes & fees

Aug 18 - Aug 19

13. Hyatt House Orlando Airport

22.7 km from Windward Cay

Suzanne

NT$3,991 total

includes taxes & fees

Aug 19 - Aug 20

14. Hampton Inn & Suites Orlando Airport @ Gateway Village

22.8 km from Windward Cay

Ianna

NT$3,392 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$3,233 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$2,177 total

includes taxes & fees

Aug 16 - Aug 17

17. Wyndham Garden Orlando Airport

19.9 km from Windward Cay

Gabriel

NT$3,251 total

includes taxes & fees

Sep 6 - Sep 7

18. Star Island Resort and Club

2.4 km from Windward Cay

Caroline

NT$3,776 total

includes taxes & fees

Aug 18 - Aug 19

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

9 km from Windward Cay

Steven

NT$2,608 total

includes taxes & fees

Aug 30 - Aug 31

20. The Vietta Hotel

2.6 km from Windward Cay

Andrea

NT$2,814 total

includes taxes & fees

Aug 14 - Aug 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

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"The staff all of them were great and the facilities top notch. Will go again next time we are in Orlando."

Walt Disney World Swan

10/10 Excellent

"The Walt Disney World Swan delivers a deluxe Disney vacation experience. Its prime location lets guests walk or take a boat to Epcot and Disney's Hollywood Studios, while offering top-tier amenities like the Grotto pool and official deluxe park perks. Location and Travel Walk to Epcot and Disney's Hollywood Studios in minutes. Catch free water taxis (Friendship Boats) right outside. Stroll over to the lively Disney's BoardWalk area. Perks and Benefits Enjoy Early Theme Park Entry every single day.Access exclusive Extended Evening Hours in select parks.Book Lightning Lane passes early like other deluxe resort guests.Pools and FunRelax at the massive Grotto pool with a waterfall and slide.Unwind on clean white-sand beaches with hammocks.Rent fun swan paddle boats on the water.Rooms and FoodSleep well in newly updated, clean, and quiet rooms.Eat at amazing on-site spots like Kimonos sushi or Il Molino.Earn or use Marriott Bonvoy loyalty points for your stay."

The Grove Resort & Water Park Orlando

10/10 Excellent

"Would definitely come back ! Staff was so friendly and helpful and when I texted them got an immediate response and if not immediate then a pretty quick response within 20 minutes. Pool stays open late . They do keep you informed of any closures due to rain and when it opens back up they also notify you. They text you about daily activities you can do with the kiddos! We had an amazing time and already are planning to come back !"

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. 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

Kompose Boutique Resort at Theme Parks

Frequently asked questions

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