A golf course with a large hotel and residential area.

Search 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
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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 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, (1,615 reviews)
"Very nice place."
United States
Nguyen
The price is Rp1.962.625
Rp2.227.579 total
includes taxes & fees
18 Oct - 19 Oct
Embassy Suites by Hilton 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.

2. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.4 out of 10, Very good, (5,363 reviews)
"Breakfast was awesome Great value!!"
United States
Darius
The price is Rp475.203
Rp1.148.637 total
includes taxes & fees
12 Oct - 13 Oct
Palazzo Lakeside Hotel
A hotel with a central entrance, palm trees, and a clear sky.

3. 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, (2,570 reviews)
"All the accommodations near the hotel was a plus"
United States
Diahiana
The price is Rp1.346.005
Rp1.527.716 total
includes taxes & fees
2 Nov - 3 Nov
Comfort Suites Maingate East
A spacious lobby with a large chandelier, a reception desk, and a view of the outside through large windows.

4. 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, (1,494 reviews)
"Loved my stay looking forward to my next."
United States
Shawn
The price is Rp1.655.873
Rp2.184.235 total
includes taxes & fees
18 Oct - 19 Oct
Star Island Resort and Club
A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

5. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
9.0 out of 10, Wonderful, (4,040 reviews)
"Exellent place to stay!!"
United States
Antonio
The price is Rp816.732
Rp926.992 total
includes taxes & fees
12 Oct - 13 Oct
Seasons Florida Resort
A swimming pool with a blue slide, surrounded by palm trees and a fenced area.

6. 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, (3,768 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 Rp851.992
Rp1.373.317 total
includes taxes & fees
5 Nov - 6 Nov
Radisson Hotel Orlando Lake Buena Vista South
A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

7. 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, (6,144 reviews)
"Always love staying here"
United States
Brianne
The price is Rp2.890.510
Rp3.251.823 total
includes taxes & fees
28 Oct - 29 Oct
Drury Plaza Hotel Orlando - Disney Springs Area
A hotel with a large pool, palm trees, and a waterfall feature.

8. 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, (5,333 reviews)
"We stay here all the time and love it!"
United States
Brittany
The price is Rp3.382.911
Rp4.571.047 total
includes taxes & fees
16 Oct - 17 Oct
Caribe Royale Orlando, WorldHotels Elite
A modern living room with a large flat-screen TV, a white sofa, and a coffee table.

9. 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, (3,248 reviews)
"Great place to stay!!"
United States
Mirtha
The price is Rp1.095.419
Rp1.852.547 total
includes taxes & fees
20 Oct - 21 Oct
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
A swimming pool with a covered seating area and palm trees in the background.

10. 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, (2,770 reviews)
"Excellent place to stay"
United States
Crystal
The price is Rp1.031.698
Rp1.475.773 total
includes taxes & fees
19 Oct - 20 Oct
Legacy Vacation Resorts - Kissimmee/Orlando
A modern reception desk with a wooden finish and the logo 'THE VIETTA'.

11. The Vietta Hotel

The Vietta Hotel
2.0 star property
2.6 km from Windward Cay
7.8 out of 10, Good, (1,005 reviews)
"It was nice and clean Hotel with all anemities close by."
Canada
Fakhar-ud-din
The price is Rp1.018.095
Rp1.561.846 total
includes taxes & fees
2 Nov - 3 Nov
The Vietta Hotel
An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

12. 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, (3,162 reviews)
"Great hotel in a great location for Disney"
United States
Anthony
The price is Rp2.219.476
Rp3.342.639 total
includes taxes & fees
29 Oct - 30 Oct
Wyndham Grand Orlando Resort Bonnet Creek
A swimming pool with people in the water, including a person in a green and red inflatable ring.

13. Buena Vista Suites Orlando

Buena Vista Suites Orlando
4.0 star property
5.7 km from Windward Cay
9.2 out of 10, Wonderful, (2,576 reviews)
"Fantastic place to stay and wonderful rooms with a family!"
United States
Jonathan
The price is Rp2.164.526
Rp2.898.317 total
includes taxes & fees
25 Oct - 26 Oct
Buena Vista Suites Orlando
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, (2,368 reviews)
"Great stay, amazing pool."
United States
Elizabeth
The price is Rp2.881.739
Rp4.248.776 total
includes taxes & fees
28 Oct - 29 Oct
Hyatt Regency Grand Cypress
An arcade with various gaming machines, including racing and motorcycle games.

15. 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, (4,024 reviews)
"It was a great stay!"
United States
Rosalinda
The price is Rp1.252.930
Rp2.013.638 total
includes taxes & fees
14 Oct - 15 Oct
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

16. 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, (6,037 reviews)
"Amazing stay"
United States
Nicolas
The price is Rp465.374
Rp1.320.296 total
includes taxes & fees
12 Oct - 13 Oct
Kompose Boutique Resort at Theme Parks
A hotel room with a bed, a desk, a chair, a sofa, and a TV.

17. Pestana Orlando Suites - Lake Buena Vista

Pestana Orlando Suites - Lake Buena Vista
4.0 star property
9.6 km from Windward Cay
9.4 out of 10, Exceptional, (2,396 reviews)
"Great place to stay!"
United States
Tracy
The price is Rp1.503.516
Rp1.924.143 total
includes taxes & fees
28 Oct - 29 Oct
Pestana Orlando Suites - Lake Buena Vista
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, (5,607 reviews)
"We love this hotel"
United States
Lauren
The price is Rp1.354.059
Rp1.523.316 total
includes taxes & fees
28 Oct - 29 Oct
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.

19. Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
6.8 km from Windward Cay
8.8 out of 10, Excellent, (1,637 reviews)
"Stayed there many times"
United States
David
The price is Rp1.539.314
Rp2.397.213 total
includes taxes & fees
4 Nov - 5 Nov
Meliá Orlando Celebration
A large hotel with multiple floors, a central courtyard, and a reflective water feature.

20. 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, (2,278 reviews)
"A great place to stay!"
United States
Camille
The price is Rp1.475.773
Rp1.660.245 total
includes taxes & fees
28 Oct - 29 Oct
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
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 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

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

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

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Ample dining options and top 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 top golf courses and fun-filled water parks 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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

8/10 Good
"The room was very clean! The only down side was the location of the room due to building was going on right behind it"
Anita 3-night trip
Posted less than an hour ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Frequently asked questions

What's it like in Windward Cay?
Travellers to the Windward Cay neighbourhood in Kissimmee will be sure to enjoy their stay.
How many hotels will I be able to find in Windward Cay?
Expedia has 33 hotels and other accommodation options 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! The majority of hotel reservations are fully refundable if you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Put your dates in and click on "Search", then you can filter by "fully refundable" to review the best options available in Windward Cay.
What is there to do around this Kissimmee neighbourhood?
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.