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 31 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.

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Dates

February 2026

March 2026

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Our top choices for Windward Cay hotels

4716-4-ww-blend of Relaxation and Convenience

Windward Cay

NT$94,695 total

includes taxes & fees

Feb 14 - Feb 15

Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Gary

NT$5,694 total

includes taxes & fees

Feb 4 - Feb 5

Wyndham Garden Lake Buena Vista – Disney Springs® Area

8.2 km from Windward Cay

Jose Carlos

NT$5,106 total

includes taxes & fees

Feb 23 - Feb 24

Home2 Suites by Hilton Orlando at Flamingo Crossings

16.3 km from Windward Cay

VIMAL

NT$3,875 total

includes taxes & fees

Feb 9 - Feb 10

Holiday Inn Express Hotel & Suites Ocoee East by IHG

26.8 km from Windward Cay

Luisa

NT$4,549 total

includes taxes & fees

Feb 3 - Feb 4

Aloft Orlando Lake Buena Vista

9.5 km from Windward Cay

Terry

NT$3,186 total

includes taxes & fees

Feb 10 - Feb 11

The Delaney Hotel

25.9 km from Windward Cay

Cate

Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

Homewood Suites by Hilton Orlando at Flamingo Crossings

16.4 km from Windward Cay

ALTON

NT$4,597 total

includes taxes & fees

Feb 9 - Feb 10

Hilton Vacation Club Grand Beach Orlando

6.3 km from Windward Cay

Giselle

NT$5,313 total

includes taxes & fees

Feb 22 - Feb 23

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

9.8 km from Windward Cay

Rosalba

NT$3,301 total

includes taxes & fees

Feb 8 - Feb 9

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

16.3 km from Windward Cay

Bethany L

NT$5,042 total

includes taxes & fees

Feb 10 - Feb 11

Candlewood Suites Orlando - Lake Buena Vista by IHG

9.3 km from Windward Cay

Lisa

NT$3,280 total

includes taxes & fees

Feb 9 - Feb 10

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

9.5 km from Windward Cay

Jordana

NT$3,914 total

includes taxes & fees

Feb 23 - Feb 24

Holiday Inn Resort Orlando Suites - Waterpark by IHG

6.2 km from Windward Cay

Matthew

NT$3,562 total

includes taxes & fees

Feb 3 - Feb 4

avid hotel Orlando International Airport by IHG

21.2 km from Windward Cay

Pamela

NT$4,584 total

includes taxes & fees

Mar 3 - Mar 4

Hyatt Place Orlando/Lake Buena Vista

9.1 km from Windward Cay

Yuberka

NT$3,315 total

includes taxes & fees

Feb 11 - Feb 12

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

16.4 km from Windward Cay

Christian

NT$4,090 total

includes taxes & fees

Feb 23 - Feb 24

Element Orlando Universal Blvd.

15.1 km from Windward Cay

Lynne

NT$3,267 total

includes taxes & fees

Feb 8 - Feb 9

Hampton Inn & Suites Orlando Airport @ Gateway Village

22.8 km from Windward Cay

Nancy

NT$5,196 total

includes taxes & fees

Feb 24 - Feb 25

6 outdoor pools, free cabanas, pool umbrellas

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

7.2 km from Windward Cay

Nancy

NT$4,062 total

includes taxes & fees

Feb 26 - Feb 27

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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 showing landscape views

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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Magic Kingdom® Park showing rides and interior views as well as a couple

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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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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Universal Studios Orlando featuring signage, a city and night scenes

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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Downtown Orlando

Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation.

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