Find hotels in Windward Cay, Orlando from NT$2,737

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Our top choices for Windward Cay hotels

Exterior
La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North
3.0 star property
22.8 km from Windward Cay
7.4 out of 10, Good, (847)
"nice and clean staff was great also"
United States
sumatran
The price is NT$2,471
NT$2,779 total
includes taxes & fees
Dec 17 - Dec 18
La Quinta Inn & Suites by Wyndham Orlando Airport North
Reception
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
8.8 out of 10, Excellent, (3302)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is NT$1,895
NT$2,151 total
includes taxes & fees
Dec 15 - Dec 16
Seasons Florida Resort
Lobby
Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL
3.0 star property
22.9 km from Windward Cay
7.8 out of 10, Good, (4307)
"Friendly staff and good breakfast!"
United States
wendy
The price is NT$2,562
NT$2,882 total
includes taxes & fees
Dec 15 - Dec 16
Country Inn & Suites by Radisson, Orlando Airport, FL
Outdoor banquet area
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
13.4 km from Windward Cay
9.4 out of 10, Exceptional, (4361)
"Great resort "
United States
Camille
The price is NT$3,469
NT$3,902 total
includes taxes & fees
Dec 18 - Dec 19
Rosen Shingle Creek
Lobby
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
17.1 km from Windward Cay
9.4 out of 10, Exceptional, (1363)
"The staff was really friendly and the property was nice and cozy "
United States
curtis
The price is NT$2,932
NT$3,299 total
includes taxes & fees
Dec 15 - Dec 16
Hyatt House Orlando International Drive
In-room safe, laptop workspace, blackout drapes, iron/ironing board
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.2 out of 10, Very Good, (5157)
"Overall good experience would stay again"
United States
Jacquelyn
The price is NT$852
NT$2,028 total
includes taxes & fees
Dec 15 - Dec 16
Palazzo Lakeside Hotel
Outdoor pool, pool umbrellas, sun loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
16.5 km from Windward Cay
7.4 out of 10, Good, (3901)
"Room was good hotel was nice and clean"
United States
Amy
The price is NT$1,944
NT$2,818 total
includes taxes & fees
Dec 17 - Dec 18
Wyndham I-Drive Avanti Resort & Conference Center
Exterior
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG
3.5 star property
11.8 km from Windward Cay
8.4 out of 10, Very Good, (1043)
"Great place - hardworking staff!"
United States
Theodore
The price is NT$2,184
NT$3,098 total
includes taxes & fees
Dec 17 - Dec 18
Holiday Inn Resort Kissimmee by the Parks by IHG
Lobby lounge
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
9.5 km from Windward Cay
8.8 out of 10, Excellent, (1909)
"Great stay"
United States
Gerard
The price is NT$2,433
NT$2,737 total
includes taxes & fees
Dec 18 - Dec 19
Aloft Orlando Lake Buena Vista
Exterior
Hampton Inn & Suites Orlando Airport @ Gateway Village

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, (2454)
"Great location to airport and food choices. "
United States
Aliza
The price is NT$3,249
NT$3,655 total
includes taxes & fees
Dec 23 - Dec 24
Hampton Inn & Suites Orlando Airport @ Gateway Village
Lobby
Embassy Suites by Hilton Orlando Lake Buena Vista South

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
9.4 out of 10, Exceptional, (1238)
"Nice place very good"
United States
Hugo
The price is NT$3,555
NT$4,035 total
includes taxes & fees
Dec 21 - Dec 22
Embassy Suites by Hilton Orlando Lake Buena Vista South
Fitness facility
Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
20 km from Windward Cay
9.0 out of 10, Wonderful, (4010)
"Very clean hotel and easy experience checking in and out "
United States
Arielle
The price is NT$2,620
NT$2,948 total
includes taxes & fees
Dec 15 - Dec 16
Wyndham Garden Orlando Airport
Free daily on-the-go breakfast
Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL
3.5 star property
12.2 km from Windward Cay
9.0 out of 10, Wonderful, (3657)
"Great location clean rooms "
United States
Erika
The price is NT$2,471
NT$2,779 total
includes taxes & fees
Dec 21 - Dec 22
Tru By Hilton Orlando Convention Center Area, FL
View from room
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando
3.0 star property
13.8 km from Windward Cay
8.6 out of 10, Excellent, (5406)
"Room very clean and amazing location."
United States
Mehilin
The price is NT$2,526
NT$2,842 total
includes taxes & fees
Dec 15 - Dec 16
Rosen Inn at Pointe Orlando
Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
3.5 star property
17.5 km from Windward Cay
9.0 out of 10, Wonderful, (5737)
"Great stay "
Canada
Marjorie
The price is NT$4,149
NT$4,667 total
includes taxes & fees
Dec 15 - Dec 16
Universal's Cabana Bay Beach Resort
Exterior
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway
3.0 star property
11.4 km from Windward Cay
8.0 out of 10, Very Good, (3915)
"Always great to stay there "
United States
Giandre
The price is NT$1,572
NT$2,422 total
includes taxes & fees
Jan 4 - 2026/1/5
Ramada by Wyndham Kissimmee Gateway
Terrace/patio
Hyatt House Orlando Airport

Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
22.7 km from Windward Cay
9.6 out of 10, Exceptional, (2789)
"Great stay close to airport and plenty of dining available "
United States
Lonnie
The price is NT$3,556
NT$4,001 total
includes taxes & fees
Dec 21 - Dec 22
Hyatt House Orlando Airport
Restaurant
Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport
3.0 star property
23.5 km from Windward Cay
8.8 out of 10, Excellent, (3751)
"Beautiful property, excellent staff and love the shuttle service to the airport!"
United States
Robert
The price is NT$2,442
NT$2,748 total
includes taxes & fees
Dec 16 - Dec 17
Wingate by Wyndham - Orlando International Airport
Business center
Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
19.7 km from Windward Cay
9.0 out of 10, Wonderful, (431)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is NT$2,741
NT$3,083 total
includes taxes & fees
Jan 13 - 2026/1/14
Spark by Hilton Orlando near Universal
Lobby
Fairfield Inn By Marriott Orlando Airport

Fairfield Inn By Marriott Orlando Airport

Fairfield Inn By Marriott Orlando Airport
3.5 star property
23.4 km from Windward Cay
9.2 out of 10, Wonderful, (2347)
"Clean great staff , good breakfast "
United States
Paul Douglas
The price is NT$2,890
NT$3,251 total
includes taxes & fees
Dec 17 - Dec 18
Fairfield Inn By Marriott Orlando Airport
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.
International Drive showing landscape views

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.

Magic Kingdom® Park showing rides and interior views as well as a couple
Photo by ©Disney
Open Photo by ©Disney

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.

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.

Universal Studios Orlando featuring signage, a city and night scenes

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

Downtown Orlando

Downtown Orlando

Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation.

Top Windward Cay Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Was there for a pre-cruise night/day for EPIC Universe. It was perfect!"
Tonya 1-night trip
Posted 20 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Explore a world of travel with Expedia

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 28 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.