A golf course with a large hotel and residential area.

Find hotels in Windward Cay, Orlando

  • 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

Check prices for these dates

This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

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

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
3 km from Windward Cay
9.6 out of 10, Exceptional, (1,553 reviews)
"I have been there for 2 years and the property is excellent, the staff in everywhere (Front desk, bar, restaurant, housekeeping) courteous and friendly. The breakfast is spectacular."
United States
Luis
The price is ￥13,870
￥15,744 total
includes taxes & fees
Oct 4 - Oct 5
Embassy Suites by Hilton Orlando Lake Buena Vista South
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

2. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
9.0 out of 10, Wonderful, (3,919 reviews)
"Clean facilities, rooms and common areas very well maintained, very friendly staff, highly recommend."
United States
Stephen
The price is ￥6,881
￥7,810 total
includes taxes & fees
Oct 15 - Oct 16
Seasons Florida Resort
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

3. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
16.2 km from Windward Cay
9.4 out of 10, Exceptional, (6,030 reviews)
"Nice place to stay"
United States
Subhransu
The price is ￥13,913
￥15,653 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites by Hilton Orlando at Flamingo Crossings
A swimming pool with people in the water, including a person in a green and red inflatable ring.

4. Buena Vista Suites Orlando

Buena Vista Suites Orlando
4.0 star property
5.7 km from Windward Cay
9.2 out of 10, Wonderful, (2,550 reviews)
"Great location"
United States
gloria
The price is ￥18,917
￥25,274 total
includes taxes & fees
Oct 6 - Oct 7
Buena Vista Suites Orlando
A hotel with a large pool, palm trees, and a waterfall feature.

5. Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite
4.5 star property
5.7 km from Windward Cay
9.2 out of 10, Wonderful, (5,289 reviews)
"Great place to stay!"
United States
Carnesha
The price is ￥29,153
￥39,391 total
includes taxes & fees
Sep 16 - Sep 17
Caribe Royale Orlando, WorldHotels Elite
A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

6. Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
4.0 star property
8.4 km from Windward Cay
9.8 out of 10, Exceptional, (6,086 reviews)
"Great place to stay with a family!"
United States
Keller
The price is ￥21,632
￥24,336 total
includes taxes & fees
Sep 20 - Sep 21
Drury Plaza Hotel Orlando - Disney Springs Area
An outdoor patio area with seating, a bar, and a fire feature.

7. Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
22.7 km from Windward Cay
9.6 out of 10, Exceptional, (2,892 reviews)
"It was a lovely place to stay."
United States
suketu
The price is ￥16,968
￥19,089 total
includes taxes & fees
Sep 27 - Sep 28
Hyatt House Orlando Airport
A swimming pool with a blue slide, surrounded by palm trees and a fenced area.

8. Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
3 km from Windward Cay
8.8 out of 10, Excellent, (3,814 reviews)
"The rooms were nice and clean. The area was convenient and close to Disney world, a variety of shops and restaurants. The pool area was beautiful and my kids really enjoyed the lazy river.."
United States
Dustin
The price is ￥6,657
￥11,057 total
includes taxes & fees
Sep 28 - Sep 29
Radisson Hotel Orlando Lake Buena Vista South
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.

9. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.4 out of 10, Very good, (5,341 reviews)
"Nice stay"
United States
Arcenio
The price is ￥4,513
￥10,373 total
includes taxes & fees
Sep 23 - Sep 24
Palazzo Lakeside Hotel
A hotel atrium with a central fountain, palm trees, and a circular seating area.

10. Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport
4.0 star property
21.3 km from Windward Cay
9.4 out of 10, Exceptional, (4,457 reviews)
"Great place to stay!"
United States
Debbie
The price is ￥33,781
￥38,004 total
includes taxes & fees
Sep 20 - Sep 21
Hyatt Regency Orlando International Airport
A modern indoor patio with a fire pit table, seating, a bar area, and large windows.

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

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
3.0 star property
9.5 km from Windward Cay
8.8 out of 10, Excellent, (3,632 reviews)
"Great location, friendly staff, clean areas!"
United States
Harold T
The price is ￥12,494
￥14,055 total
includes taxes & fees
Sep 27 - Sep 28
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.

12. Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
16.3 km from Windward Cay
9.4 out of 10, Exceptional, (2,695 reviews)
"Awesome hotel to stay!!"
United States
Eduardo
The price is ￥20,111
￥22,626 total
includes taxes & fees
Sep 27 - Sep 28
Homewood Suites by Hilton Orlando at Flamingo Crossings
A modern gym with treadmills, stationary bikes, and elliptical machines.

13. Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
19.9 km from Windward Cay
9.0 out of 10, Wonderful, (4,177 reviews)
"Friendly staff, clean room and nice pool. Would stay here again."
United States
Kagen
The price is ￥11,013
￥12,390 total
includes taxes & fees
Sep 20 - Sep 21
Wyndham Garden Orlando Airport
A multi-story hotel with a swimming pool, parking, and a landscaped area.

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

Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
3.0 star property
9.5 km from Windward Cay
8.8 out of 10, Excellent, (2,345 reviews)
"Excellent Staff and rooms super clean"
United States
Nelson
The price is ￥12,186
￥13,709 total
includes taxes & fees
Sep 16 - Sep 17
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
A modern dining area with a large table, chairs, and a coffee station.

15. avid hotel Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG
2.5 star property
21.2 km from Windward Cay
9.2 out of 10, Wonderful, (2,223 reviews)
"Great standard service and location, the lift to and from the airport was super useful"
United States
Joan
The price is ￥13,574
￥15,271 total
includes taxes & fees
Sep 21 - Sep 22
avid hotel Orlando International Airport by IHG
An outdoor seating area with green chairs and umbrellas, a fire pit, and a building with large windows in the background.

16. Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
3.0 star property
22.8 km from Windward Cay
9.4 out of 10, Exceptional, (2,859 reviews)
"Great stay as always!"
Canada
Alexandria
The price is ￥14,419
￥16,221 total
includes taxes & fees
Sep 20 - Sep 21
Hampton Inn & Suites Orlando Airport @ Gateway Village
A modern hotel lobby with a large flat-screen TV, a blue sofa, a round wooden table, and a curved reception desk.

17. Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
21.1 km from Windward Cay
9.0 out of 10, Wonderful, (2,001 reviews)
"This hotel was amazing. Super clean and helpful staff made this property pleasant to stay at. Breakfast was also good and well prepared."
United States
kaalliyah
The price is ￥15,132
￥17,025 total
includes taxes & fees
Sep 16 - Sep 17
Cambria Hotel Orlando Airport
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
16.4 km from Windward Cay
9.4 out of 10, Exceptional, (5,530 reviews)
"Very friendly front staff, close to Disney, good breakfast for price!"
United States
Lauren
The price is ￥13,671
￥15,380 total
includes taxes & fees
Oct 5 - Oct 6
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A modern living room with a large flat-screen TV, a white sofa, and a coffee table.

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

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
3.0 star property
3.2 km from Windward Cay
8.6 out of 10, Excellent, (3,229 reviews)
"Great family friendly environment"
United States
Teresa
The price is ￥4,998
￥10,924 total
includes taxes & fees
Sep 16 - Sep 17
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
An arcade with various gaming machines, including racing and motorcycle games.

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

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
7.6 km from Windward Cay
8.6 out of 10, Excellent, (4,034 reviews)
"Great service pool and pool bar are great rooms are nice and big great place to stay"
United States
juan
The price is ￥9,440
￥15,826 total
includes taxes & fees
Sep 17 - Sep 18
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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.
Photo by Gary Burke
Open Photo by Gary Burke

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.

A large Ferris wheel with a blue light, surrounded by a water fountain display and palm trees.

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.

A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.
Photo by Peter Sutton
Open Photo by Peter Sutton

Florida Center

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

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.

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.

Top Windward Cay Hotel Reviews

Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Very great hotel"
Jordonna 1-night trip
Posted 1 hour ago
Marriott's Grande Vista

Frequently asked questions

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.