Kissimmee, Florida, United States of America

Hotels in Windward Cay


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Find out more about Windward Cay

What's Windward Cay Like?

If you want to find the perfect part of the city to explore, look no further than Windward Cay. Places to visit like Medieval Times and Capone's Dinner Show are not far away. 192 Flea Market and Shingle Creek Regional Park are a couple of more places to see nearby.

Where are the Best Places to Stay in Windward Cay?

We have 47 accommodations in the neighborhood. Some of the top places to stay in Windward Cay:

House / Villa - Kissimmee

Waterfront vacation home with private pool, kitchen
  • • Garden • Central location

Christines Villa

Comfortable vacation home with private pool, kitchen
  • • Free parking • Free in-room WiFi • Outdoor pool

My Lake-Side Villa!!

Family-friendly vacation home with private pool, kitchen
  • • Water park • Spa tub

Windward Cay 4707

Comfortable vacation home with kitchen
  • • Free parking • Free WiFi • Outdoor pool

Luxurious Private Villa, Perfectly Located and with Tranquil Pool

Family-friendly villa with private pool, kitchen
  • • Water park • Garden

How to Get to Windward Cay

Flying to:

  • • Orlando International Airport (MCO), 13.1 mi (21.1 km) from Windward Cay
  • • Kissimmee, FL (ISM-Kissimmee Gateway), 2.4 mi (3.9 km) from Windward Cay

Things to See and Do in and around Windward Cay

Things to Do near Windward Cay:

  • • Medieval Times (0.7 mi/1.1 km away)
  • • Capone's Dinner Show (1 mi/1.6 km away)
  • • 192 Flea Market (1.2 mi/1.9 km away)
  • • Congo River Golf (1.3 mi/2.1 km away)
  • • Osceola County Welcome Center and History Museum (1.5 mi/2.4 km away)

Things to See near Windward Cay:

  • • Shingle Creek Regional Park (1.3 mi/2 km away)
  • • Lake Cecile (1.4 mi/2.2 km away)
  • • Florida Technical College (2 mi/3.2 km away)
  • • Kissimmee Sports Arena and Rodeo (2.5 mi/4 km away)
  • • Osceola County Clerk of the Court (4 mi/6.4 km away)

When Is the Best Time to Visit Kissimmee?

  • • Hottest months: July, August, June, September (average 81°F)
  • • Coldest months: January, December, February, March (average 62°F)
  • • Rainiest months: August, June, July, September (average 7 inches of rainfall)

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