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Our top choices for Windward Cay hotels

La Quinta Inn & Suites by Wyndham Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport
3.0 star property
22.8 km from Windward Cay
7.4 out of 10, Good, (1,973 reviews)
The price is ฿2,455
฿2,762 total
includes taxes & fees
9 Jun - 10 Jun
La Quinta Inn & Suites by Wyndham 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, (3,009 reviews)
"Nice place to stay"
United States
LaToya
The price is ฿3,559
฿4,004 total
includes taxes & fees
7 Jun - 8 Jun
Hyatt House Orlando Airport

Fairfield Inn By Marriott Orlando Airport

Fairfield Inn By Marriott Orlando Airport
3.5 star property
23.4 km from Windward Cay
9.0 out of 10, Wonderful, (2,454 reviews)
"Breakfast was great and the airport shuttle was timely and pleasant"
United States
Cheryl
The price is ฿2,430
฿2,733 total
includes taxes & fees
24 May - 25 May
Fairfield Inn By Marriott Orlando Airport

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, (2,677 reviews)
"Very clean and kind staff good breakfast"
United States
Brittany
The price is ฿3,320
฿3,735 total
includes taxes & fees
24 May - 25 May
Hampton Inn & Suites Orlando Airport @ Gateway Village

Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport
3.0 star property
23.4 km from Windward Cay
8.8 out of 10, Excellent, (3,976 reviews)
"Breakfast was good , we love the waffle"
United States
Ana
The price is ฿2,733
฿3,074 total
includes taxes & fees
20 May - 21 May
Wingate by Wyndham - Orlando International Airport

Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport
3.0 star property
22.9 km from Windward Cay
8.2 out of 10, Very good, (5,731 reviews)
"Nice clean friendly hotel"
Canada
cindy
The price is ฿2,909
฿3,273 total
includes taxes & fees
19 May - 20 May
Ramada by Wyndham Suites Orlando Airport

Holiday Inn Express Orlando International Airport by IHG

Holiday Inn Express Orlando International Airport by IHG
2.5 star property
20.9 km from Windward Cay
9.0 out of 10, Wonderful, (2,006 reviews)
"Breakfast was good and the airport shuttle extremely convenient."
United States
Ayesha
The price is ฿3,167
฿3,563 total
includes taxes & fees
17 Jun - 18 Jun
Holiday Inn Express Orlando International Airport by IHG

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
11.5 km from Windward Cay
9.4 out of 10, Exceptional, (4,057 reviews)
"The breakfast and pool was great"
United States
Emmanuelle
The price is ฿902
฿2,469 total
includes taxes & fees
20 May - 21 May
Kompose Boutique Resort at Theme Parks

Hyatt Place Orlando Airport

Hyatt Place Orlando Airport
3.0 star property
22.9 km from Windward Cay
9.0 out of 10, Wonderful, (1,723 reviews)
"The staff were great and the shuttle back and forth to the airport was a great help"
United States
Danny
The price is ฿3,330
฿3,747 total
includes taxes & fees
1 Jun - 2 Jun
Hyatt Place Orlando Airport

Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL
3.0 star property
22.8 km from Windward Cay
7.8 out of 10, Good, (4,669 reviews)
"Nice clean hotel with friendly staff!"
United States
matthais
The price is ฿2,909
฿3,273 total
includes taxes & fees
24 May - 25 May
Country Inn & Suites by Radisson, Orlando Airport, FL

avid hotel Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG
2.5 star property
21.2 km from Windward Cay
9.2 out of 10, Wonderful, (2,201 reviews)
"Great stay "
Canada
Jordan
The price is ฿2,821
฿3,173 total
includes taxes & fees
26 May - 27 May
avid hotel Orlando International Airport by IHG

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
13.4 km from Windward Cay
9.4 out of 10, Exceptional, (4,798 reviews)
"Great golf resort , great food "
United States
David
The price is ฿3,892
฿4,378 total
includes taxes & fees
26 May - 27 May
Rosen Shingle Creek

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, (1,822 reviews)
"The best the hotel was so so ver clean had a great stay "
United States
Kayanna
The price is ฿3,036
฿3,416 total
includes taxes & fees
25 May - 26 May
Hyatt House Orlando International Drive

Hampton Inn Orlando-International Airport

Hampton Inn Orlando-International Airport
2.5 star property
23.3 km from Windward Cay
9.0 out of 10, Wonderful, (1,908 reviews)
"Perfect stay"
United States
Mario
The price is ฿2,784
฿3,132 total
includes taxes & fees
25 May - 26 May
Hampton Inn Orlando-International Airport

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
16.1 km from Windward Cay
8.6 out of 10, Excellent, (1,400 reviews)
"Excellent place to stay , come back "
United States
Jeannette
The price is ฿3,040
฿3,420 total
includes taxes & fees
25 May - 26 May
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport
4.0 star property
23.2 km from Windward Cay
8.8 out of 10, Excellent, (2,363 reviews)
"Staff was really friendly and my room was very clean. Shuttle to airport was really convenient."
United States
Anthony
The price is ฿3,631
฿4,085 total
includes taxes & fees
24 May - 25 May
DoubleTree by Hilton Orlando Airport

Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

Hilton Garden Inn Orlando I-4 Millenia Blvd Mall
3.0 star property
19.2 km from Windward Cay
9.0 out of 10, Wonderful, (764 reviews)
"The bar staff and morning front desk were extremely pleasant!! So glad I stayed here for my first trip to Orlando."
United States
Kennedy
The price is ฿3,186
฿3,584 total
includes taxes & fees
20 May - 21 May
Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
21.1 km from Windward Cay
8.8 out of 10, Excellent, (1,905 reviews)
"Clean rooms , safe and quiet environment, great food and close to the airport."
United States
Tekarrah
The price is ฿3,164
฿3,559 total
includes taxes & fees
8 Jun - 9 Jun
Cambria Hotel Orlando Airport

Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
19.9 km from Windward Cay
9.0 out of 10, Wonderful, (4,067 reviews)
"Great place to stay. "
United States
scott
The price is ฿2,586
฿2,909 total
includes taxes & fees
20 May - 21 May
Wyndham Garden Orlando Airport

Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown
3.0 star property
28.8 km from Windward Cay
9.4 out of 10, Exceptional, (1,004 reviews)
"I love to stay here, the staff the hotel everything is excellent."
United States
Eduardo
The price is ฿3,996
฿4,496 total
includes taxes & fees
24 May - 25 May
Courtyard by Marriott Orlando Downtown
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.

Where to stay in Windward Cay

Find the best Windward Cay areas for the activities you enjoy most.

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.

Bay Lake

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

Champions Gate

Ample dining options and top 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.

Florida Center

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

Downtown Orlando

One of the most popular neighborhoods in Florida, this bustling area is full of art galleries, shops, bars and restaurants.

Top Windward Cay Hotel Reviews

Frequently asked questions

What's it like in Windward Cay?
Travellers to the Windward Cay neighbourhood in Kissimmee will be sure to enjoy their stay.
How many hotels will I be able to find in Windward Cay?
Expedia has 33 hotels and other accommodation options 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! The majority of hotel reservations are fully refundable if you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Put your dates in and click on "Search", then you can filter by "fully refundable" to review the best options available in Windward Cay.
What is there to do around this Kissimmee neighbourhood?
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.