Top Windward Cay Hotels

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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

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

10/10 Excellent

"Room was suffice not a lot of space but clean and pest free. Nice large bathroom with shower shelves to place items. The breakfast was excellent with fruits, hot eggs and bacon sausage just like the pictures. Parking was easy and very full lot, though stranger noises coming from the bushes at night. I would definitely stay here again and again. In walking distance to a flea market and McDonalds very nice location. The theme park shuttle is free but picks up too early before the parks even close."

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"We checked in late on a Sunday evening in June having traveled from Brazil a little tired and befuddled. Rob was working the front desk alone and was very busy. Nevertheless, he seemed to be helping everyone at the same time. We were grateful for his professionalism and kindness as we were wanting to get to our room asap. He made sure we got everything we needed (extra linens, wifi pw, snacks) cheerfully and swiftly. Later in the trip I had some issues with a second check in (we left for 1 day to go to Brazil game in Miami), and Julian stepped up and made sure we were squared away, again with courtesy and kindness. Great place, room, breakfast, pool area, etc. If I'm ever in Orlando again, I will definitely stay here!"

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

10/10 Excellent

"Our stay was so wonderful, we’ll definitely come back. The staff was very attentive and went above and beyond to make our stay a memorable one. They knew it was our first visit to Disney World and they gave us a Disney treat to start off our stay, a welcomed surprise. They were all kind and we felt very taken care of. The shuttle was so convenient and was the first stop at Disney so we got to the park quickly. Would highly recommend for anyone looking for a nice resort that’s close but doesn’t want to stay at the other Disney hotels."

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Excellent facilities, grounds are well kept and very beautiful. 10/10 for families. Our one bed villa was very modern , well equipped and spotlessly clean . My only complaint was the lack of sun shades at the pool ( only 2 at our pool ) with temperatures reaching 100 degrees when we were there it was unbearable without a sun shade. Anyone with children could not have stayed more than an hour at the pool before it was dangerous for children. Also the parking fee of $30 per day would really make me think about booking again. We were only there for 5 days but we usually stay 10/12 days in Orlando and this will significantly add to our budget."

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"The rooms were clean I did have somebody come in to service the air conditioner, but then other than that it was nice and cold. The laundry washing dryer in your room so everything worked out well. The weather was beautiful. The only issue we had was at the pool they didn’t have enough people to work in the pool area at the park so they limited what was open, but that was for everyone’s safety that m was just for the one day, but everything else was wonderful."

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.

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.

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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

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Frequently asked questions

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