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, Capone's Dinner Show and Pirate's Island Adventure Golf are a couple of additional sights to visit in Kissimmee.

Top Windward Cay Hotels

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Our top choices for Windward Cay hotels

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

3 km from Windward Cay

Rashida

NT$4,188 total

includes taxes & fees

Aug 9 - Aug 10

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

2. Buena Vista Suites Orlando

5.7 km from Windward Cay

Sherry

NT$5,006 total

includes taxes & fees

Aug 10 - Aug 11

3. Caribe Royale Orlando

5.6 km from Windward Cay

Jonathan

NT$6,911 total

includes taxes & fees

Aug 8 - Aug 9

4. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Justine

NT$5,108 total

includes taxes & fees

Aug 9 - Aug 10

In-room safe, blackout drapes, iron/ironing board, cribs (free)

5. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

Ashley

NT$2,953 total

includes taxes & fees

Aug 16 - Aug 17

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

9.5 km from Windward Cay

jean-pierre

NT$2,950 total

includes taxes & fees

Aug 2 - Aug 3

7. Seasons Florida Resort

1.6 km from Windward Cay

Heather

NT$2,161 total

includes taxes & fees

Aug 16 - Aug 17

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

8. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Alexsandra

NT$2,294 total

includes taxes & fees

Aug 6 - Aug 7

9. Home2 Suites by Hilton Orlando at Flamingo Crossings

16.2 km from Windward Cay

Sandra

NT$3,554 total

includes taxes & fees

Aug 9 - Aug 10

Coffee/tea maker, mini-fridge, shared microwave

10. AC Hotel by Marriott Orlando Lake Buena Vista

8.4 km from Windward Cay

Alessandra

NT$3,606 total

includes taxes & fees

Jul 30 - Jul 31

11. Wyndham Grand Orlando Resort Bonnet Creek

8.1 km from Windward Cay

Rachel

NT$6,746 total

includes taxes & fees

Aug 8 - Aug 9

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

12. Meliá Orlando Celebration

6.8 km from Windward Cay

Lisa

NT$4,336 total

includes taxes & fees

Aug 9 - Aug 10

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

3.2 km from Windward Cay

Alexander

NT$2,633 total

includes taxes & fees

Aug 2 - Aug 3

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

9.5 km from Windward Cay

Ana E

NT$2,914 total

includes taxes & fees

Aug 23 - Aug 24

15. Hyatt Regency Orlando International Airport

21.3 km from Windward Cay

Beau

NT$6,811 total

includes taxes & fees

Aug 3 - Aug 4

Outdoor pool, a heated pool, pool umbrellas, sun loungers

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

7.6 km from Windward Cay

gloria

NT$3,506 total

includes taxes & fees

Aug 9 - Aug 10

17. Star Island Resort and Club

2.4 km from Windward Cay

Meredith

NT$3,951 total

includes taxes & fees

Aug 2 - Aug 3

18. Rosen Shingle Creek

13.4 km from Windward Cay

Guillermo

NT$5,507 total

includes taxes & fees

Jul 30 - Jul 31

19. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

16.3 km from Windward Cay

Jodi

NT$3,684 total

includes taxes & fees

Aug 2 - Aug 3

Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

20. Homewood Suites by Hilton Orlando at Flamingo Crossings

16.3 km from Windward Cay

Kaitlin

NT$3,853 total

includes taxes & fees

Aug 9 - Aug 10

View all properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties