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 Medieval Times, Kissimmee Go-Karts, and Capone's Dinner Show. While you're out sightseeing, Pirate's Island Adventure Golf and Pioneer Village at Shingle Creek are a couple of additional sights to visit in Kissimmee.

Top Windward Cay Hotels

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Our top choices for Windward Cay hotels

Hyatt Regency Orlando International Airport

21.3 km from Windward Cay

RICHARD

NT$6,780 total

includes taxes & fees

Jul 6 - Jul 7

Hyatt House Orlando Airport

22.7 km from Windward Cay

LaToya

NT$3,946 total

includes taxes & fees

Jul 20 - Jul 21

La Quinta Inn & Suites by Wyndham Orlando Airport

22.8 km from Windward Cay

Robert

NT$2,650 total

includes taxes & fees

Jul 8 - Jul 9

Hampton Inn & Suites Orlando Airport @ Gateway Village

22.8 km from Windward Cay

Jose

NT$3,349 total

includes taxes & fees

Jul 21 - Jul 22

Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Xiomara

NT$5,031 total

includes taxes & fees

Jul 17 - Jul 18

Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room

Universal's Cabana Bay Beach Resort

17.5 km from Windward Cay

Pamela

NT$5,381 total

includes taxes & fees

Jul 19 - Jul 20

Rosen Shingle Creek

13.4 km from Windward Cay

John

NT$4,271 total

includes taxes & fees

Jul 20 - Jul 21

Wyndham Garden Orlando Airport

19.9 km from Windward Cay

Brandon

NT$3,329 total

includes taxes & fees

Jul 5 - Jul 6

Country Inn & Suites by Radisson, Orlando Airport, FL

22.8 km from Windward Cay

Rebecca

NT$3,031 total

includes taxes & fees

Jul 13 - Jul 14

EVEN Hotel Orlando International Airport by IHG

21.2 km from Windward Cay

Mark

NT$3,336 total

includes taxes & fees

Jul 20 - Jul 21

Courtyard by Marriott Orlando Downtown

28.8 km from Windward Cay

jelena

NT$4,081 total

includes taxes & fees

Jul 5 - Jul 6

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

16.4 km from Windward Cay

Rene

NT$2,346 total

includes taxes & fees

Jul 20 - Jul 21

Premium bedding, pillowtop beds, in-room safe, desk

Hyatt Place Orlando Airport

22.9 km from Windward Cay

Stacey

NT$3,946 total

includes taxes & fees

Jul 19 - Jul 20

Margaritaville Resort Orlando with H2O Waterpark

13.8 km from Windward Cay

tammy

NT$7,859 total

includes taxes & fees

Jul 27 - Jul 28

Wingate by Wyndham - Orlando International Airport

23.4 km from Windward Cay

Patrinella

NT$3,045 total

includes taxes & fees

Jul 27 - Jul 28

avid hotel Orlando International Airport by IHG

21.2 km from Windward Cay

Jacob

NT$2,798 total

includes taxes & fees

Jul 30 - Jul 31

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$3,196 total

includes taxes & fees

Jul 14 - Jul 15

3 restaurants; breakfast, lunch, and dinner served

The Grove Resort & Water Park Orlando

18.3 km from Windward Cay

Jessica Judy Ann

NT$9,614 total

includes taxes & fees

Jul 20 - Jul 21

Home2 Suites by Hilton Orlando at Flamingo Crossings

16.2 km from Windward Cay

Marcy

NT$2,405 total

includes taxes & fees

Jul 20 - Jul 21

Wyndham Garden Lake Buena Vista – Disney Springs® Area

8.2 km from Windward Cay

Heather

NT$4,133 total

includes taxes & fees

Jul 5 - Jul 6

View all properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

Top Windward Cay Hotel Reviews

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

10/10 Excellent

"We loved our stay at the Waldorf Astoria, it was the perfect balance being close to Disney World but being a fabulous sanctuary in the evenings, wonderful staff and dining experiences. Thoroughly recommend this hotel!!"

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"⭐⭐⭐⭐⭐ Our stay at Kompose Boutique Resort exceeded all of our expectations! From the moment we arrived, the front desk staff made us feel welcome with their friendly and professional service. The breakfast was outstanding, with fresh, delicious food and a great variety of options every morning. The pool was absolutely amazing—we spent a lot of time there and truly loved it. It was clean, relaxing, and one of the highlights of our stay. The rooms were modern, spotless, and very comfortable. Everything felt brand new, and the attention to cleanliness was excellent. If you’re looking for a beautiful, clean, and relaxing place to stay with exceptional customer service, Kompose Boutique Resort is the perfect choice. We highly recommend it and will definitely be coming back on our next visit!"

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Please verify if the rooms have elevator access. Our room was beautiful but was on 3rd floor and we carried our carryon all the way to 3rd floor. They have bell boy service but upon arrival or leaving we carried our own luggage from 3rd floor. The food is not great inside sheraton, try outside places."

Hyatt Regency Orlando International Airport

8/10 Good

"We had a very short but nice stay at the hotel. Nice location for very late arrival. The staff was welcoming and offered us an upgrade so we wouldn’t have to walk too far. The room was nice, spacious and surprisingly quieter for being at an airport. We barely hear some construction going on around 1am but no planes taking off or landing. I can’t put a 5 stars because it’s an airport hotel, I wouldn’t come here unless forced to stay before or after a flight. But it is a very nice hotel."

Find hotels in Windward Cay, Orlando

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Our top choices for Windward Cay hotels

Hyatt Regency Orlando International Airport

Hyatt House Orlando Airport

La Quinta Inn & Suites by Wyndham Orlando Airport

Hampton Inn & Suites Orlando Airport @ Gateway Village

Drury Plaza Hotel Orlando - Disney Springs Area

Universal's Cabana Bay Beach Resort

Rosen Shingle Creek

Wyndham Garden Orlando Airport

Country Inn & Suites by Radisson, Orlando Airport, FL

EVEN Hotel Orlando International Airport by IHG

Courtyard by Marriott Orlando Downtown

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

Hyatt Place Orlando Airport

Margaritaville Resort Orlando with H2O Waterpark

Wingate by Wyndham - Orlando International Airport

avid hotel Orlando International Airport by IHG

Ramada by Wyndham Suites Orlando Airport

The Grove Resort & Water Park Orlando

Home2 Suites by Hilton Orlando at Flamingo Crossings

Wyndham Garden Lake Buena Vista – Disney Springs® Area

Where to stay in Windward Cay

International Drive District

Bay Lake

Reunion

Champions Gate

Florida Center

Top Windward Cay Hotel Reviews

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Frequently asked questions

Explore a world of travel with Expedia