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, Capone's Dinner Show and Pirate's Island Adventure Golf are a couple of additional sights to visit in Kissimmee.

Top Windward Cay Hotels

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Our top choices for Windward Cay hotels

Kompose Boutique Resort at Theme Parks

11.5 km from Windward Cay

Noel

NT$2,943 total

includes taxes & fees

Jul 13 - Jul 14

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

16.1 km from Windward Cay

Tracy

NT$1,889 total

includes taxes & fees

Aug 7 - Aug 8

Hyatt Regency Orlando International Airport

21.3 km from Windward Cay

RICHARD

NT$6,793 total

includes taxes & fees

Aug 3 - Aug 4

La Quinta Inn & Suites by Wyndham Orlando Airport

22.8 km from Windward Cay

Robert

NT$2,513 total

includes taxes & fees

Jul 15 - Jul 16

Hampton Inn & Suites Orlando Airport @ Gateway Village

22.8 km from Windward Cay

Jose

NT$3,212 total

includes taxes & fees

Jul 13 - Jul 14

DoubleTree by Hilton at the Entrance to Universal Orlando

18.9 km from Windward Cay

Dianelly

NT$3,536 total

includes taxes & fees

Aug 3 - Aug 4

Hyatt House Orlando International Drive

17.1 km from Windward Cay

Idoel

NT$3,630 total

includes taxes & fees

Aug 3 - Aug 4

Hilton Garden Inn Orlando Airport

23.1 km from Windward Cay

milton

NT$2,503 total

includes taxes & fees

Jul 20 - Jul 21

Vacation Village Orlando, Celebration

6.5 km from Windward Cay

Martena

NT$3,702 total

includes taxes & fees

Jul 26 - Jul 27

Rosen Shingle Creek

13.4 km from Windward Cay

John

NT$4,284 total

includes taxes & fees

Jul 19 - Jul 20

EVEN Hotel Orlando International Airport by IHG

21.2 km from Windward Cay

Mark

NT$3,163 total

includes taxes & fees

Aug 2 - Aug 3

Courtyard by Marriott across Universal Orlando

18.6 km from Windward Cay

hilary

NT$3,738 total

includes taxes & fees

Jul 20 - Jul 21

Wingate by Wyndham - Orlando International Airport

23.4 km from Windward Cay

Patrinella

NT$2,841 total

includes taxes & fees

Jul 14 - Jul 15

Wyndham Garden Orlando Airport

19.9 km from Windward Cay

Brandon

NT$3,345 total

includes taxes & fees

Jul 8 - Jul 9

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

16.4 km from Windward Cay

Rene

NT$3,127 total

includes taxes & fees

Aug 4 - Aug 5

DoubleTree by Hilton Orlando Airport

23.2 km from Windward Cay

Kimberly

NT$2,967 total

includes taxes & fees

Jul 27 - Jul 28

Hyatt House Orlando Airport

22.7 km from Windward Cay

LaToya

NT$4,241 total

includes taxes & fees

Jul 19 - Jul 20

Studio Suite, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Accessible) | Premium bedding, in-room safe, desk, blackout drapes

Ramada by Wyndham Suites Orlando Airport

22.9 km from Windward Cay

Kareisha Grant

NT$2,620 total

includes taxes & fees

Jul 13 - Jul 14

Hampton Inn Orlando-International Airport

23.3 km from Windward Cay

John

NT$3,153 total

includes taxes & fees

Jul 28 - Jul 29

Country Inn & Suites by Radisson, Orlando Airport, FL

22.8 km from Windward Cay

Rebecca

NT$2,780 total

includes taxes & fees

Jul 28 - Jul 29

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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 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.

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The entrance to the Hollywood Studios area with a large sign and distinctive architecture.

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.

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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.

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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.

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A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.

Florida Center

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

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Top Windward Cay Hotel Reviews

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"My family and I had an amazing time, we enjoyed the amenities, the lazy river was our favorite spot to be at. The breakfast was delicious and the staff were very hospitable, especially Rob from front desk. We will be visiting again."

Hyatt Regency Orlando International Airport

10/10 Excellent

"My stay at the Hyatt Regency Orlando International Airport was absolutely outstanding! From the moment I checked in, the staff was warm, welcoming, and professional. The room was spotless, spacious, and incredibly comfortable, with a peaceful atmosphere that made it easy to relax before my flight. The location couldn't be more convenient—being directly inside the airport made traveling completely stress-free. Despite being at a busy airport, the room was surprisingly quiet, allowing for a great night's sleep. The hotel offers excellent amenities, including delicious dining options, a beautiful rooftop pool, and exceptional customer service. Every employee I encountered went above and beyond to ensure my stay was enjoyable. I highly recommend the Hyatt Regency Orlando International Airport to anyone traveling through Orlando. Whether you're staying for one night or several, this hotel delivers comfort, convenience, and first-class hospitality. I will definitely stay here again!"

Find hotels in Windward Cay, Orlando

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Treat yourself

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Our top choices for Windward Cay hotels

Kompose Boutique Resort at Theme Parks

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

Hyatt Regency Orlando International Airport

La Quinta Inn & Suites by Wyndham Orlando Airport

Hampton Inn & Suites Orlando Airport @ Gateway Village

DoubleTree by Hilton at the Entrance to Universal Orlando

Hyatt House Orlando International Drive

Hilton Garden Inn Orlando Airport

Vacation Village Orlando, Celebration

Rosen Shingle Creek

EVEN Hotel Orlando International Airport by IHG

Courtyard by Marriott across Universal Orlando

Wingate by Wyndham - Orlando International Airport

Wyndham Garden Orlando Airport

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

DoubleTree by Hilton Orlando Airport

Hyatt House Orlando Airport

Ramada by Wyndham Suites Orlando Airport

Hampton Inn Orlando-International Airport

Country Inn & Suites by Radisson, Orlando Airport, FL

Where to stay in Windward Cay

International Drive District

Bay Lake

Reunion

Champions Gate

Florida Center

Top Windward Cay Hotel Reviews

Kompose Boutique Resort at Theme Parks

Frequently asked questions

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