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

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Filter by

Star rating

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 lobby with a reception desk, seating area, and a decorative flower arrangement.

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, (1,640 reviews)
"Beautiful hotel! Great breakfast and nice happy hour."
United States
Linda
The price is NT$3,846
NT$4,365 total
includes taxes & fees
Nov 2 - Nov 3
Embassy Suites by Hilton Orlando Lake Buena Vista South
A hotel with a central entrance, palm trees, and a clear sky.

2. Comfort Suites Maingate East

Comfort Suites Maingate East
3.0 star property
4.6 km from Windward Cay
8.4 out of 10, Very good, (2,587 reviews)
"Clean room, outdoor pool, restaurant on site, complementary breakfast daily."
United States
Vanessa
The price is NT$2,448
NT$2,778 total
includes taxes & fees
Nov 23 - Nov 24
Comfort Suites Maingate East
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.

3. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.4 out of 10, Very good, (5,371 reviews)
"Great stay"
United States
Juan
The price is NT$183
NT$1,317 total
includes taxes & fees
Oct 29 - Oct 30
Palazzo Lakeside Hotel
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

4. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
9.0 out of 10, Wonderful, (4,065 reviews)
"Exellent place to stay!!"
United States
Antonio
The price is NT$1,711
NT$1,942 total
includes taxes & fees
Oct 25 - Oct 26
Seasons Florida Resort
A hotel pool area with a water slide, palm trees, and a bridge.

5. 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, (3,743 reviews)
"Great location close to everything. The place was easy to get to and the check in was super easy."
United States
JORGE
The price is NT$1,407
NT$2,337 total
includes taxes & fees
Nov 5 - Nov 6
Radisson Hotel Orlando Lake Buena Vista South
A spacious lobby with a large chandelier, a reception desk, and a view of the outside through large windows.

6. Star Island Resort and Club

Star Island Resort and Club
3.5 star property
2.4 km from Windward Cay
8.4 out of 10, Very good, (1,496 reviews)
"Quiet, peaceful resort with lots of activities"
United States
Monica
The price is NT$2,930
NT$3,880 total
includes taxes & fees
Nov 22 - Nov 23
Star Island Resort and Club
A modern living room with a large flat-screen TV, a white sofa, and a coffee table.

7. 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, (3,238 reviews)
"Great place to stay!!"
United States
Mirtha
The price is NT$1,635
NT$2,965 total
includes taxes & fees
Oct 29 - Oct 30
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

8. 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, (6,168 reviews)
"Very nice place to stay while visiting Disney...loved available shuttle to and from which made my family trip to Disney streamlined with no hassle. Very clean and courteous place to stay with the family."
United States
IvIr
The price is NT$5,265
NT$5,923 total
includes taxes & fees
Nov 23 - Nov 24
Drury Plaza Hotel Orlando - Disney Springs Area
A kitchen with wooden cabinets, a microwave, a refrigerator, and two bar stools.

9. Club Sevilla

Club Sevilla
2.0 star property
0.7 km from Windward Cay
9.0 out of 10, Wonderful, (1,003 reviews)
"Very nice resort"
United States
Eric
The price is NT$1,640
NT$2,031 total
includes taxes & fees
Oct 25 - Oct 26
Club Sevilla
A hotel room with two beds, a desk with a chair, a television, and large abstract paintings on the wall.

10. Buena Vista Suites Orlando

Buena Vista Suites Orlando
4.0 star property
5.7 km from Windward Cay
9.2 out of 10, Wonderful, (2,598 reviews)
"Beautiful property Great stay"
United States
Pamela
The price is NT$3,658
NT$4,959 total
includes taxes & fees
Nov 24 - Nov 25
Buena Vista Suites Orlando
A hotel with a swimming pool, palm trees, and a large building with multiple floors.

11. 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, (5,332 reviews)
"Great property and staff."
United States
Rachel
The price is NT$5,673
NT$7,775 total
includes taxes & fees
Nov 19 - Nov 20
Caribe Royale Orlando, WorldHotels Elite
A swimming pool with a covered seating area and palm trees in the background.

12. Legacy Vacation Resorts - Kissimmee/Orlando

Legacy Vacation Resorts - Kissimmee/Orlando
3.5 star property
2.8 km from Windward Cay
7.8 out of 10, Good, (2,771 reviews)
"Excellent place to stay"
United States
Crystal
The price is NT$1,688
NT$2,471 total
includes taxes & fees
Oct 30 - Oct 31
Legacy Vacation Resorts - Kissimmee/Orlando
A modern reception desk with a wooden finish and the logo 'THE VIETTA'.

13. The Vietta Hotel

The Vietta Hotel
2.0 star property
2.6 km from Windward Cay
7.8 out of 10, Good, (1,002 reviews)
"It was nice and clean Hotel with all anemities close by."
Canada
Fakhar-ud-din
The price is NT$1,782
NT$2,761 total
includes taxes & fees
Nov 2 - Nov 3
The Vietta Hotel
Pool

14. Hyatt Regency Grand Cypress

Hyatt Regency Grand Cypress
4.0 star property
9.2 km from Windward Cay
9.2 out of 10, Wonderful, (2,389 reviews)
"Great hotel!"
United States
Christine
The price is NT$4,955
NT$7,409 total
includes taxes & fees
Nov 22 - Nov 23
Hyatt Regency Grand Cypress
A hotel with a swimming pool surrounded by lounge chairs and palm trees.

15. Holiday Inn Express & Suites Orlando at SeaWorld by IHG

Holiday Inn Express & Suites Orlando at SeaWorld by IHG
2.5 star property
11.3 km from Windward Cay
9.2 out of 10, Wonderful, (1,888 reviews)
"Great spot and very close to the parks."
United States
Tyler
The price is NT$2,999
NT$3,374 total
includes taxes & fees
Oct 28 - Oct 29
Holiday Inn Express & Suites Orlando at SeaWorld by IHG
An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

16. Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
4.0 star property
8.1 km from Windward Cay
8.8 out of 10, Excellent, (3,158 reviews)
"Great hotel in a great location for Disney"
United States
Anthony
The price is NT$4,036
NT$6,079 total
includes taxes & fees
Oct 30 - Oct 31
Wyndham Grand Orlando Resort Bonnet Creek
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

17. 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, (5,663 reviews)
"Great breakfast and wonderful staff! Highly coming back here again!"
United States
Juana
The price is NT$2,466
NT$2,775 total
includes taxes & fees
Nov 17 - Nov 18
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A large hotel with multiple floors, a central courtyard, and a reflective water feature.

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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
16.3 km from Windward Cay
9.6 out of 10, Exceptional, (2,281 reviews)
"We were very pleased with our stay here. The location, the rooms and breakfast were great!"
United States
Michael
The price is NT$3,048
NT$3,429 total
includes taxes & fees
Nov 18 - Nov 19
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

19. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
11.5 km from Windward Cay
9.4 out of 10, Exceptional, (6,184 reviews)
"Excellent place to stay!!"
United States
Theresa
The price is NT$1,080
NT$2,666 total
includes taxes & fees
Oct 28 - Oct 29
Kompose Boutique Resort at Theme Parks
A modern hotel with "La Quinta" signage, featuring a prominent entrance and a covered outdoor area.

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

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
3.0 star property
9.8 km from Windward Cay
8.8 out of 10, Excellent, (3,228 reviews)
"Good place to stay!!!"
United States
Antonio
The price is NT$2,754
NT$3,098 total
includes taxes & fees
Oct 28 - Oct 29
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
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

Compare top hotels in Windward Cay

A spacious lobby with a reception desk, seating area, and a decorative flower arrangement.

Embassy Suites by Hilton Orlando Lake Buena Vista South

4.0 star property
3 km from Windward Cay
View
A hotel with a central entrance, palm trees, and a clear sky.

Comfort Suites Maingate East

3.0 star property
4.6 km from Windward Cay
View
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.

Palazzo Lakeside Hotel

3.0 star property
2.7 km from Windward Cay
View
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

Seasons Florida Resort

2.0 star property
1.6 km from Windward Cay
View
A hotel pool area with a water slide, palm trees, and a bridge.

Radisson Hotel Orlando Lake Buena Vista South

3.5 star property
3 km from Windward Cay
View
9.6
Exceptional
1,640 reviews
8.4
Very good
2,587 reviews
8.4
Very good
5,371 reviews
9.0
Wonderful
4,065 reviews
8.8
Excellent
3,743 reviews
The price is NT$3,846
NT$4,365 total
includes taxes & fees
Nov 2 - Nov 3
The price is NT$2,448
NT$2,778 total
includes taxes & fees
Nov 23 - Nov 24
The price is NT$183
NT$1,317 total
includes taxes & fees
Oct 29 - Oct 30
The price is NT$1,711
NT$1,942 total
includes taxes & fees
Oct 25 - Oct 26
The price is NT$1,407
NT$2,337 total
includes taxes & fees
Nov 5 - Nov 6
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • No WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • No Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • No WiFi included
  • No Parking

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 blue lights, surrounded by a cityscape with illuminated buildings and a tall green tower.

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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"We enjoyed every moment. Coming back next year."
Carolina 5-night trip
Posted 1 hour ago
Universal's Cabana Bay Beach Resort

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.

Explore a world of travel with Expedia