Hotels in Windward Cay, Orlando

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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, (1,969 reviews)
"Pretty good stay overall would come back for sure"
United States
Rahmel
The price is CA $103
CA $116 total
includes taxes & fees
Jun 9 - Jun 10
La Quinta Inn & Suites by Wyndham Orlando Airport

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, (4,052 reviews)
"The breakfast and pool was great"
United States
Emmanuelle
The price is CA $38
CA $104 total
includes taxes & fees
May 19 - May 20
Kompose Boutique Resort at Theme Parks

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, (2,452 reviews)
"Breakfast was great and the airport shuttle was timely and pleasant"
United States
Cheryl
The price is CA $113
CA $127 total
includes taxes & fees
Jun 14 - Jun 15
Fairfield Inn By Marriott 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, (3,007 reviews)
"Nice place to stay"
United States
LaToya
The price is CA $150
CA $169 total
includes taxes & fees
Jun 7 - Jun 8
Hyatt House Orlando 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, (1,393 reviews)
"Excellent place to stay , come back "
United States
Jeannette
The price is CA $116
CA $130 total
includes taxes & fees
May 21 - May 22
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

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, (2,674 reviews)
"Very clean and kind staff good breakfast"
United States
Brittany
The price is CA $140
CA $157 total
includes taxes & fees
May 24 - May 25
Hampton Inn & Suites Orlando Airport @ Gateway Village

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, (4,665 reviews)
"Nice clean hotel with friendly staff!"
United States
matthais
The price is CA $123
CA $138 total
includes taxes & fees
May 27 - May 28
Country Inn & Suites by Radisson, Orlando Airport, FL

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
13.4 km from Windward Cay
9.4 out of 10, Exceptional, (4,796 reviews)
"Great golf resort , great food "
United States
David
The price is CA $144
CA $162 total
includes taxes & fees
May 26 - May 27
Rosen Shingle Creek

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, (4,169 reviews)
"Excellent stay"
United States
Clint
The price is CA $274
CA $308 total
includes taxes & fees
May 20 - May 21
Hyatt Regency Orlando International Airport

Hyatt Place Orlando Airport

Hyatt Place Orlando Airport
3.0 star property
22.9 km from Windward Cay
9.0 out of 10, Wonderful, (1,720 reviews)
"The staff were great and the shuttle back and forth to the airport was a great help"
United States
Danny
The price is CA $140
CA $158 total
includes taxes & fees
Jun 1 - Jun 2
Hyatt Place Orlando 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, (5,726 reviews)
"Nice clean friendly hotel"
Canada
cindy
The price is CA $136
CA $153 total
includes taxes & fees
May 19 - May 20
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, (2,004 reviews)
"Breakfast was good and the airport shuttle extremely convenient."
United States
Ayesha
The price is CA $128
CA $144 total
includes taxes & fees
Jun 15 - Jun 16
Holiday Inn Express Orlando International Airport by IHG

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 CA $115
CA $129 total
includes taxes & fees
May 19 - May 20
Wingate by Wyndham - Orlando International Airport

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, (1,815 reviews)
"The best the hotel was so so ver clean had a great stay "
United States
Kayanna
The price is CA $131
CA $147 total
includes taxes & fees
May 31 - Jun 1
Hyatt House Orlando International Drive

Orlando Palms Hotel

Orlando Palms Hotel
2.5 star property
16 km from Windward Cay
7.8 out of 10, Good, (2,817 reviews)
"Fantastic hotel at a fantastic price and location"
United States
Issac
The price is CA $75
CA $101 total
includes taxes & fees
May 19 - May 20
Orlando Palms Hotel

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, (1,907 reviews)
"Perfect stay"
United States
Mario
The price is CA $117
CA $132 total
includes taxes & fees
May 25 - May 26
Hampton Inn Orlando-International Airport

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 CA $153
CA $172 total
includes taxes & fees
May 25 - May 26
DoubleTree by Hilton Orlando Airport

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, (4,787 reviews)
"Great stay"
United States
La Shaunn
The price is CA $128
CA $144 total
includes taxes & fees
Jun 1 - Jun 2
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
19.9 km from Windward Cay
9.0 out of 10, Wonderful, (4,065 reviews)
"Great place to stay. "
United States
scott
The price is CA $138
CA $155 total
includes taxes & fees
May 31 - Jun 1
Wyndham Garden Orlando Airport

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
21.1 km from Windward Cay
8.8 out of 10, Excellent, (1,904 reviews)
"Clean rooms , safe and quiet environment, great food and close to the airport."
United States
Tekarrah
The price is CA $133
CA $150 total
includes taxes & fees
Jun 8 - Jun 9
Cambria Hotel 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.

Where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods 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

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.

Florida Center

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

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

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.
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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