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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8/10 Good

"The room was clean and as pictured. I loved the pool and bar at the Fountains. I would have loved the pool and splash pad area to be bigger or connected to the other pool area by the activities center. Other than that the texting feature to reach guest relations was really helpful and convenient. It’s a family friendly resort that was conveniently located to Disney Springs and a good distance to iDrive. Loved my stay overall"

Rosen Inn Lake Buena Vista

8/10 Good

"Overall, I’d say this hotel is acceptable for the price. It was one of the more affordable options, so I wasn’t expecting luxury. That said, the property definitely feels outdated and looks like it hasn’t been renovated in years. At night, the traffic noise from the road was very noticeable, making it difficult to sleep. When we first entered the room, there was an unpleasant smell, and we ended up buying an air freshener to make it more comfortable. The bathroom sink drained very slowly, the toilet took a long time to refill after flushing, and the carpet was extremely dirty. For the price, I can’t be too critical because you get what you pay for. This was simply our experience, and I hope it helps future guests know what to expect. On the positive side, the pool was nice and well maintained, and the staff was very friendly and welcoming throughout our stay."

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Included Breakfast buffet was wonderful! Our server Gabby was fantastic! The pool was good. Disappointed with how expensive drinks at the bar were ($20 for a single Pina Colado), as well as the prices in the gift shop & sweets shops ($5 for a can of soda/tea). The customer service in the gift shop could have been better. Did NOT enjoy being accosted in the lobby by the Hilton staff trying to see us vacation stuff. Jazlyn was very nice checking when we checked in and again checked out. Also the elevators were terribly slow & the ice machine didn’t work on our floor and there was zero vending anywhere! 😬☹️"

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

La Quinta Inn & Suites by Wyndham Orlando Airport

Hyatt House Orlando Airport

Hampton Inn & Suites Orlando Airport @ Gateway Village

EVEN Hotel Orlando International Airport by IHG

Fairfield Inn By Marriott Orlando Airport

Ramada by Wyndham Suites Orlando Airport

Wingate by Wyndham - Orlando International Airport

Kompose Boutique Resort at Theme Parks

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

Country Inn & Suites by Radisson, Orlando Airport, FL

Hyatt Place Orlando Airport

Hyatt House Orlando International Drive

Wyndham Garden Orlando Airport

DoubleTree by Hilton Orlando Airport

Hampton Inn Orlando-International Airport

Holiday Inn Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG

Rosen Shingle Creek

Courtyard by Marriott across Universal Orlando

Where to stay in Windward Cay

International Drive District

Bay Lake

Reunion

Champions Gate

Florida Center

Top Windward Cay Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Frequently asked questions

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