Aerial panoramic view of Celebration, Florida, USA. December 3, 2025.

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Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

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Our top choices for Windward Cay hotels

Lobby

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, (1,516 reviews)
"Very nice hotel for the price"
United States
Nick
The price is NT$3,651
NT$4,144 total
includes taxes & fees
Aug 30 - Aug 31
Embassy Suites by Hilton Orlando Lake Buena Vista South
Exterior

2. 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, (5,251 reviews)
"Great place to stay, food was good, service was good, the kids loved the pool."
United States
Jhon
The price is NT$5,414
NT$7,460 total
includes taxes & fees
Aug 17 - Aug 18
Caribe Royale Orlando, WorldHotels Elite
Reception

3. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
9.0 out of 10, Wonderful, (3,789 reviews)
"Nice and a good place to stay."
United States
Joel
The price is NT$1,704
NT$1,934 total
includes taxes & fees
Aug 17 - Aug 18
Seasons Florida Resort
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

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, (2,474 reviews)
"Great stay!"
United States
Alicia
The price is NT$3,575
NT$4,851 total
includes taxes & fees
Aug 20 - Aug 21
Buena Vista Suites Orlando
Property amenity

5. 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, (3,595 reviews)
"Amazing stay"
United States
Mahnoor
The price is NT$2,723
NT$3,063 total
includes taxes & fees
Aug 25 - Aug 26
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)

6. Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
6.8 km from Windward Cay
8.8 out of 10, Excellent, (1,609 reviews)
"Restaurant staff very nice and food was excellent"
United States
Carolyn
The price is NT$2,210
NT$3,672 total
includes taxes & fees
Aug 22 - Aug 23
Meliá Orlando Celebration
In-room safe, laptop workspace, blackout drapes, iron/ironing board

7. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.4 out of 10, Very Good, (5,300 reviews)
"The hotel was beautiful, we had a great time."
United States
LILLIAN
The price is NT$790
NT$1,987 total
includes taxes & fees
Aug 19 - Aug 20
Palazzo Lakeside Hotel
Exterior

8. 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, (5,902 reviews)
"Loved our stay"
United States
Kelly
The price is NT$2,545
NT$2,864 total
includes taxes & fees
Aug 26 - Aug 27
Home2 Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, sun loungers

9. 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, (6,002 reviews)
"Property very clean and staff was helpful at all times."
United States
Fatima Gail
The price is NT$4,492
NT$5,054 total
includes taxes & fees
Aug 30 - Aug 31
Drury Plaza Hotel Orlando - Disney Springs Area
Outdoor pool

10. 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, (2,354 reviews)
"Great place to stay"
United States
Ana E
The price is NT$2,531
NT$2,847 total
includes taxes & fees
Aug 19 - Aug 20
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
Water park

11. 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, (3,880 reviews)
"Love staying at this place. They do need to get more floaties for the lazy river besides that love being here"
United States
Soraida
The price is NT$1,359
NT$2,269 total
includes taxes & fees
Sep 7 - Sep 8
Radisson Hotel Orlando Lake Buena Vista South
Exterior

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, (3,079 reviews)
"This was definitely a great place to stay for the price and we would stay here again."
United States
Ian
The price is NT$4,331
NT$6,386 total
includes taxes & fees
Aug 22 - Aug 23
Wyndham Grand Orlando Resort Bonnet Creek
Reception

13. 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, (3,212 reviews)
"This was a very fun, clean, and kid-friendly hotel. Everything about it was supportive of family fun."
United States
Wendy
The price is NT$769
NT$1,963 total
includes taxes & fees
Aug 17 - Aug 18
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
Front of property - evening/night

14. 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, (2,963 reviews)
"Good area nice hotel nice and clean good service"
United States
Jorge L
The price is NT$2,854
NT$3,211 total
includes taxes & fees
Aug 17 - Aug 18
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
Exterior

15. 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, (4,389 reviews)
"Enjoyed stay"
United States
Tracy
The price is NT$6,054
NT$6,811 total
includes taxes & fees
Sep 2 - Sep 3
Hyatt Regency Orlando International Airport
Reception

16. The Vietta Hotel

The Vietta Hotel
2.0 star property
2.6 km from Windward Cay
7.6 out of 10, Good, (1,001 reviews)
"The room is clean, food is ok."
United States
Fangfei
The price is NT$1,822
NT$2,795 total
includes taxes & fees
Aug 17 - Aug 18
The Vietta Hotel
Free daily buffet breakfast

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, (5,373 reviews)
"Great location, breakfast was extensive, and the rooms were nice and large."
United States
Andrea
The price is NT$2,369
NT$2,665 total
includes taxes & fees
Aug 31 - Sep 1
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Lobby

18. Hilton Vacation Club Polynesian Isles Kissimmee

Hilton Vacation Club Polynesian Isles Kissimmee
3.0 star property
3.9 km from Windward Cay
9.6 out of 10, Exceptional, (1,930 reviews)
"Nice room and friendly staff"
United States
Bridget
The price is NT$2,970
NT$4,098 total
includes taxes & fees
Aug 22 - Aug 23
Hilton Vacation Club Polynesian Isles Kissimmee
Exterior

19. 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, (2,207 reviews)
"Location was really close to all the parks, the breakfast was really nice to have before heading out to enjoy the great city of orlando"
Canada
harman
The price is NT$2,532
NT$2,849 total
includes taxes & fees
Aug 30 - Aug 31
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Reception

20. 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, (1,501 reviews)
"My family enjoyed our stay. I would come back for our next trip"
United States
Caroline
The price is NT$2,824
NT$3,750 total
includes taxes & fees
Aug 18 - Aug 19
Star Island Resort and Club
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.

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.

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.

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.

Top Windward Cay Hotel Reviews

Marriott's Grande Vista

Marriott's Grande Vista

8/10 Good
"The room was nice, bed was super comfy. Check-in could have been a bit more organized, had to go to 2 different desks to complete the check in...and then we find out after we already booked a package deal through Expedia and paid wayy in advanced, that we have to pay $30+/night to park, on top of what we already paid, (I feel for the price, parking should either be included or you should at least be able to reserve your very own parking spot)... and out of the 6 days we stayed we had room service twice. We ordered food on our last night there and it was okay."
John 6-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 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.

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