A golf course with a large hotel and residential area.

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Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20

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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, (1,549 reviews)
"Excellent service and breakfast"
United States
Ivandra
The price is NT$2,845
NT$3,229 total
includes taxes & fees
Oct 4 - Oct 5
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, (2,522 reviews)
"Clean, friendly staff, breakfast very good"
United States
Jose
The price is NT$4,240
NT$5,589 total
includes taxes & fees
Sep 7 - Sep 8
Buena Vista Suites Orlando
Exterior

3. 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, (5,301 reviews)
"Great place to stay!"
United States
Carnesha
The price is NT$5,505
NT$7,546 total
includes taxes & fees
Sep 7 - Sep 8
Caribe Royale Orlando, WorldHotels Elite
Water park

4. 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, (3,859 reviews)
"The hotel building and staff are great and friendly. The breakfast is okay. Continental.. simple but filling.. the pool and lazy river are awesome."
United States
yesenia
The price is NT$1,398
NT$2,306 total
includes taxes & fees
Sep 27 - Sep 28
Radisson Hotel Orlando Lake Buena Vista South
Reception

5. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
9.0 out of 10, Wonderful, (3,875 reviews)
"Nice and a good place to stay."
United States
Joel
The price is NT$1,633
NT$1,853 total
includes taxes & fees
Sep 13 - Sep 14
Seasons Florida Resort
Exterior

6. 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, (4,438 reviews)
"Great Hotel"
United States
Troy
The price is NT$6,613
NT$7,440 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Regency Orlando International Airport
Terrace/patio

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, (2,909 reviews)
"It was a lovely place to stay."
United States
suketu
The price is NT$3,480
NT$3,915 total
includes taxes & fees
Sep 20 - Sep 21
Hyatt House Orlando Airport
Property amenity

8. 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, (3,602 reviews)
"Great stay, will definitely be back."
United States
Shander Aria
The price is NT$2,436
NT$2,741 total
includes taxes & fees
Sep 10 - Sep 11
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
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, (6,045 reviews)
"Amazing hotel!"
United States
Samantha
The price is NT$4,437
NT$4,992 total
includes taxes & fees
Sep 21 - Sep 22
Drury Plaza Hotel Orlando - Disney Springs Area
In-room safe, laptop workspace, blackout drapes, iron/ironing board

10. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.4 out of 10, Very Good, (5,314 reviews)
"The hotel was beautiful, we had a great time."
United States
LILLIAN
The price is NT$633
NT$1,795 total
includes taxes & fees
Sep 7 - Sep 8
Palazzo Lakeside Hotel
Outdoor pool

11. 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, (2,353 reviews)
"Great place."
United States
Caitlin
The price is NT$2,500
NT$2,812 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
Exterior

12. 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, (5,991 reviews)
"Great place to stay, rooms are spacious, clean and beds are comfortable. Pool is nice and big, breakfast super delicious and good variety."
United States
Gloria
The price is NT$2,854
NT$3,211 total
includes taxes & fees
Sep 28 - Sep 29
Home2 Suites by Hilton Orlando at Flamingo Crossings
Coffee/tea maker, mini-fridge, shared microwave

13. 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, (1,952 reviews)
"great place!"
United States
Alexandra
The price is NT$3,132
NT$3,524 total
includes taxes & fees
Sep 7 - Sep 8
AC Hotel by Marriott Orlando Lake Buena Vista
Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)

14. Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
6.8 km from Windward Cay
8.8 out of 10, Excellent, (1,614 reviews)
"Great place to stay"
United States
Juanita
The price is NT$2,449
NT$3,929 total
includes taxes & fees
Sep 15 - Sep 16
Meliá Orlando Celebration
Reception

15. 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, (3,217 reviews)
"It was very family friendly!"
United States
Jose
The price is NT$835
NT$2,025 total
includes taxes & fees
Sep 7 - Sep 8
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
Front of property - evening/night

16. 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, (3,037 reviews)
"The hotel was nice."
United States
Stephanie
The price is NT$2,905
NT$3,268 total
includes taxes & fees
Sep 7 - Sep 8
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
Outdoor banquet area

17. Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
13.4 km from Windward Cay
9.6 out of 10, Exceptional, (5,033 reviews)
"Beautiful hotel!"
United States
Mariana
The price is NT$3,771
NT$4,243 total
includes taxes & fees
Sep 8 - Sep 9
Rosen Shingle Creek
Fitness facility

18. Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
19.9 km from Windward Cay
9.0 out of 10, Wonderful, (4,189 reviews)
"Great place to stay"
United States
Gabriel
The price is NT$2,824
NT$3,177 total
includes taxes & fees
Sep 7 - Sep 8
Wyndham Garden Orlando Airport
Exterior

19. 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, (2,847 reviews)
"Clean rooms, nice staff and very convenient from airport"
United States
Stacy
The price is NT$2,828
NT$3,181 total
includes taxes & fees
Sep 10 - Sep 11
Hampton Inn & Suites Orlando Airport @ Gateway Village
Free daily buffet breakfast

20. 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, (5,496 reviews)
"Very friendly front staff, close to Disney, good breakfast for price!"
United States
Lauren
The price is NT$3,480
NT$3,915 total
includes taxes & fees
Sep 13 - Sep 14
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Our stay at the Drury was absolutely wonderful. The staff was amazing. Valencia was a joy. We had 4 rooms for 12 people and nobody complained (except our regular complainer) his only complaint was they wouldn't do an omelet for his breakfast. I will definitely stay at a Drury in the future."
Cecil 1-night trip
Posted less than an hour ago
Drury Plaza Hotel Orlando - Disney Springs Area

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.

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