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Check prices for these dates

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

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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, (1,497 reviews)
"The hotel was nice and clean. Breakfast was delicious and the staff was very nice."
United States
Ira
The price is NT$3,690
NT$4,188 total
includes taxes & fees
Aug 9 - Aug 10
Embassy Suites by Hilton Orlando Lake Buena Vista South
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

2. Buena Vista Suites Orlando

Buena Vista Suites Orlando
4.0 star property
5.7 km from Windward Cay
9.2 out of 10, Wonderful, (2,454 reviews)
"Perfect stay with clean rooms wonderful breakfast and free parking!"
United States
Sherry
The price is NT$3,720
NT$5,020 total
includes taxes & fees
Aug 5 - Aug 6
Buena Vista Suites Orlando
Exterior

3. Caribe Royale Orlando

Caribe Royale Orlando
4.5 star property
5.6 km from Windward Cay
9.2 out of 10, Wonderful, (5,260 reviews)
"Great stay!!!"
United States
Jonathan
The price is NT$4,899
NT$6,892 total
includes taxes & fees
Aug 8 - Aug 9
Caribe Royale Orlando
Outdoor pool, sun loungers

4. 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, (5,979 reviews)
"Loved it everyone was so nice and the food was amazing"
United States
Anyela
The price is NT$4,540
NT$5,108 total
includes taxes & fees
Aug 10 - Aug 11
Drury Plaza Hotel Orlando - Disney Springs Area
In-room safe, blackout drapes, iron/ironing board, cribs (free)

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, (3,977 reviews)
"A gem of a hotel! We go every summer! Fantastic!!"
United States
Ashley
The price is NT$1,949
NT$2,945 total
includes taxes & fees
Aug 18 - Aug 19
Radisson Hotel Orlando Lake Buena Vista South
Property amenity

6. 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, (3,587 reviews)
"Nice and a clean place to stay"
United States
jean-pierre
The price is NT$2,615
NT$2,942 total
includes taxes & fees
Aug 11 - Aug 12
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
Reception

7. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
9.0 out of 10, Wonderful, (3,745 reviews)
"Great place!"
United States
Heather
The price is NT$1,899
NT$2,155 total
includes taxes & fees
Aug 18 - Aug 19
Seasons Florida Resort
In-room safe, laptop workspace, blackout drapes, iron/ironing board

8. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.4 out of 10, Very Good, (5,255 reviews)
"Everything was very clean, and the breakfast options were very good."
United States
Humberto
The price is NT$1,015
NT$2,254 total
includes taxes & fees
Aug 5 - Aug 6
Palazzo Lakeside Hotel
Exterior

9. 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, (5,857 reviews)
"Loved our stay"
United States
Kelly
The price is NT$3,159
NT$3,554 total
includes taxes & fees
Aug 11 - Aug 12
Home2 Suites by Hilton Orlando at Flamingo Crossings
Coffee/tea maker, mini-fridge, shared microwave

10. AC Hotel by Marriott Orlando Lake Buena Vista

AC Hotel by Marriott Orlando Lake Buena Vista
3.5 star property
8.4 km from Windward Cay
9.2 out of 10, Wonderful, (1,918 reviews)
"Room was clean, staff was very nice, would definitely stay again"
United States
Alessandra
The price is NT$3,197
NT$3,596 total
includes taxes & fees
Jul 31 - Aug 1
AC Hotel by Marriott Orlando Lake Buena Vista
Exterior

11. 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, (3,069 reviews)
"Excellent stay"
United States
Rachel
The price is NT$4,624
NT$6,727 total
includes taxes & fees
Aug 27 - Aug 28
Wyndham Grand Orlando Resort Bonnet Creek
Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)

12. Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
6.8 km from Windward Cay
8.8 out of 10, Excellent, (1,618 reviews)
"Very good stay"
United States
Roxana
The price is NT$2,234
NT$3,711 total
includes taxes & fees
Aug 8 - Aug 9
Meliá Orlando Celebration
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, (3,195 reviews)
"Good and unique hotel."
United States
Alexander
The price is NT$1,345
NT$2,626 total
includes taxes & fees
Aug 4 - Aug 5
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
Property entrance

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, (2,355 reviews)
"Great place to stay"
United States
Ana E
The price is NT$2,583
NT$2,906 total
includes taxes & fees
Aug 27 - Aug 28
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
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, (4,342 reviews)
"Awesome having the hotel in the airport"
United States
Beau
The price is NT$6,006
NT$6,756 total
includes taxes & fees
Aug 10 - Aug 11
Hyatt Regency Orlando International Airport
Outdoor pool, a heated pool, pool umbrellas, sun loungers

16. 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, (4,005 reviews)
"Easy to find from the Orlando airport, great proximity to Disney parks, friendly, helpful staff."
United States
gloria
The price is NT$2,139
NT$3,497 total
includes taxes & fees
Aug 11 - Aug 12
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Reception

17. 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, (1,497 reviews)
"Wonderful place and convenient area and amenities."
United States
Meredith
The price is NT$2,987
NT$3,940 total
includes taxes & fees
Aug 15 - Aug 16
Star Island Resort and Club
Outdoor banquet area

18. Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
13.4 km from Windward Cay
9.6 out of 10, Exceptional, (5,029 reviews)
"Best place to stay"
United States
Guillermo
The price is NT$4,882
NT$5,492 total
includes taxes & fees
Aug 12 - Aug 13
Rosen Shingle Creek
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, (2,198 reviews)
"Great location, clean rooms and good breakfast!"
United States
Maria
The price is NT$3,266
NT$3,674 total
includes taxes & fees
Aug 11 - Aug 12
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

20. 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, (2,626 reviews)
"Excellent location to parks. Very pleasant pool and delicious breakfast. We really enjoyed our stay."
United States
Olga
The price is NT$3,416
NT$3,842 total
includes taxes & fees
Aug 11 - Aug 12
Homewood Suites by Hilton Orlando at Flamingo Crossings
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.
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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

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

10/10 Excellent
"I like"
Evian 2-night trip
Posted 1 hour ago
Wyndham I-Drive Avanti Resort & Conference Center

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

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