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

Rebeca

NT$2,917 total

includes taxes & fees

Jun 28 - Jun 29

Hyatt Regency Orlando International Airport

21.3 km from Windward Cay

RICHARD

NT$7,083 total

includes taxes & fees

Jun 29 - Jun 30

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

16.1 km from Windward Cay

Tracy

NT$2,935 total

includes taxes & fees

Jul 14 - Jul 15

Hyatt House Orlando Airport

22.7 km from Windward Cay

LaToya

NT$4,132 total

includes taxes & fees

Jun 30 - Jul 1

La Quinta Inn & Suites by Wyndham Orlando Airport

22.8 km from Windward Cay

Robert

NT$2,689 total

includes taxes & fees

Jul 2 - Jul 3

Fairfield Inn By Marriott Orlando Airport

23.4 km from Windward Cay

Roger

NT$2,995 total

includes taxes & fees

Jun 25 - Jun 26

EVEN Hotel Orlando International Airport by IHG

21.2 km from Windward Cay

Mark

NT$3,310 total

includes taxes & fees

Jun 30 - Jul 1

Hampton Inn & Suites Orlando Airport @ Gateway Village

22.8 km from Windward Cay

Jose

NT$3,473 total

includes taxes & fees

Jun 28 - Jun 29

DoubleTree by Hilton at the Entrance to Universal Orlando

18.9 km from Windward Cay

Dianelly

NT$3,492 total

includes taxes & fees

Jul 12 - Jul 13

Wyndham Garden Orlando Airport

19.9 km from Windward Cay

Brandon

NT$2,591 total

includes taxes & fees

Jun 24 - Jun 25

avid hotel Orlando International Airport by IHG

21.2 km from Windward Cay

Jacob

NT$3,275 total

includes taxes & fees

Jul 20 - Jul 21

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$5,339 total

includes taxes & fees

Jun 29 - Jun 30

Holiday Inn Orlando International Airport by IHG

23.2 km from Windward Cay

leon

NT$3,275 total

includes taxes & fees

Jul 24 - Jul 25

Hyatt House Orlando International Drive

17.1 km from Windward Cay

Idoel

NT$4,132 total

includes taxes & fees

Jul 7 - Jul 8

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

Hyatt Place Orlando Airport

22.9 km from Windward Cay

Stacey

NT$3,616 total

includes taxes & fees

Jun 25 - Jun 26

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

16.4 km from Windward Cay

Rene

NT$3,298 total

includes taxes & fees

Jul 13 - Jul 14

Margaritaville Resort Orlando with H2O Waterpark

13.8 km from Windward Cay

tammy

NT$7,645 total

includes taxes & fees

Jul 7 - Jul 8

Hampton Inn Orlando-International Airport

23.3 km from Windward Cay

John

NT$3,123 total

includes taxes & fees

Jun 29 - Jun 30

DoubleTree by Hilton Orlando Airport

23.2 km from Windward Cay

Kimberly

NT$2,939 total

includes taxes & fees

Jul 6 - Jul 7

Country Inn & Suites by Radisson, Orlando Airport, FL

22.8 km from Windward Cay

Rebecca

NT$2,844 total

includes taxes & fees

Jul 16 - Jul 17

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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.

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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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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 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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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

The Grove Resort & Water Park Orlando

8/10 Good

"They have washer and dryer but in our room they weren’t working well. We had to dry the clothes several times for them to dry. I don’t like that they don’t clean daily or every other day at least especially if you have a long stay."