Find hotels in Windward Cay, Orlando from NT$2,597

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Dec 12 - Dec 13
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Dec 13 - Dec 14
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Dec 12 - Dec 14
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Dec 19 - Dec 21

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Our top choices for Windward Cay hotels

Free daily continental breakfast
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, (833)
"Near the beach , very nice people at the reception. "
United States
Leonie
The price is NT$2,476
NT$2,786 total
includes taxes & fees
Dec 17 - Dec 18
La Quinta Inn & Suites by Wyndham Orlando Airport North
Property grounds
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, (3289)
"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
Exterior
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, (4297)
"Friendly staff and good breakfast!"
United States
wendy
The price is NT$2,532
NT$2,848 total
includes taxes & fees
Dec 14 - Dec 15
Country Inn & Suites by Radisson, Orlando Airport, FL
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)
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, (4351)
"Great resort "
United States
Camille
The price is NT$3,469
NT$3,903 total
includes taxes & fees
Dec 15 - Dec 16
Rosen Shingle Creek
Free daily buffet breakfast
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, (1353)
"Room, Breakfast, location AAAA+ "
United States
Ahmed Gabriel
The price is NT$3,095
NT$3,482 total
includes taxes & fees
Dec 14 - Dec 15
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, (5146)
"Overall good experience would stay again"
United States
Jacquelyn
The price is NT$914
NT$2,102 total
includes taxes & fees
Dec 17 - Dec 18
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, (3884)
"Room was good hotel was nice and clean"
United States
Amy
The price is NT$1,944
NT$2,819 total
includes taxes & fees
Dec 15 - Dec 16
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, (1037)
"Great place - hardworking staff!"
United States
Theodore
The price is NT$1,966
NT$2,853 total
includes taxes & fees
Dec 14 - Dec 15
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, (1902)
"Great rooms, staff, and property!"
United States
Cindy
The price is NT$2,309
NT$2,597 total
includes taxes & fees
Dec 15 - Dec 16
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, (2447)
"Great location to airport and food choices. "
United States
Aliza
The price is NT$3,274
NT$3,684 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, (1234)
"Nice place very good"
United States
Hugo
The price is NT$2,609
NT$2,961 total
includes taxes & fees
Dec 22 - Dec 23
Embassy Suites by Hilton Orlando Lake Buena Vista South
Outdoor pool, sun loungers
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, (4003)
"Very clean hotel and easy experience checking in and out "
United States
Arielle
The price is NT$2,521
NT$2,836 total
includes taxes & fees
Dec 15 - Dec 16
Wyndham Garden Orlando Airport
Exterior
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, (3647)
"Great location clean rooms "
United States
Erika
The price is NT$2,471
NT$2,780 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, (5388)
"Room very clean and amazing location."
United States
Mehilin
The price is NT$2,246
NT$2,527 total
includes taxes & fees
Dec 14 - Dec 15
Rosen Inn at Pointe Orlando
2 outdoor pools, a heated pool, cabanas (surcharge), pool umbrellas
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, (5704)
"Great stay "
Canada
Marjorie
The price is NT$4,149
NT$4,668 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, (3905)
"Always great to stay there "
United States
Giandre
The price is NT$1,576
NT$2,427 total
includes taxes & fees
Jan 4 - 2026/1/5
Ramada by Wyndham Kissimmee Gateway
Lobby
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, (2782)
"Great stay close to airport and plenty of dining available "
United States
Lonnie
The price is NT$3,762
NT$4,233 total
includes taxes & fees
Dec 15 - Dec 16
Hyatt House Orlando Airport
Pillowtop beds, in-room safe, desk, blackout drapes
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, (3740)
"Good room, good breakfast and convenient to the airport."
United States
Mark
The price is NT$2,499
NT$2,811 total
includes taxes & fees
Dec 15 - Dec 16
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, (422)
"Wonderful staff great location to universal parks. "
United States
Desire
The price is NT$2,739
NT$3,081 total
includes taxes & fees
Jan 4 - 2026/1/5
Spark by Hilton Orlando near Universal
In-room safe, desk, iron/ironing board, free WiFi
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, (2328)
"Clean property and friendly staff. "
United States
Debra
The price is NT$2,625
NT$2,953 total
includes taxes & fees
Dec 15 - Dec 16
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Pools were great. The Flo Rider was outstanding. Best instructor ever with Eric!"
Margaret 5-night trip
Posted 17 hours ago
The Grove Resort & Water Park 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 29 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.