What's Windward Cay Like?

If you want to find the perfect part of the city to explore, look no further than Windward Cay. Old Town and Disney Springs® are a couple of the top places in the larger area worth a visit. Disney's Typhoon Lagoon Water Park and ESPN Wide World of Sports are a couple of popular sights nearby.

Where are the Best Places to Stay in Windward Cay?

We have 46 accommodations in the neighborhood. Some of the top places to stay in Windward Cay:

Christines Villa

Comfortable vacation home with private pool, kitchen

• • Free parking • Free in-room WiFi • Outdoor pool

Peaceful Windward Cay 3 Bedroom Home

2-star vacation home with outdoor pool

• • Free parking • Free Internet access

Windward Cay 4707

Comfortable vacation home with kitchen

• • Free parking • Free WiFi • Outdoor pool

Christines Villa - Wc03cce/2209

Family-friendly vacation home with private pool, kitchen

• • Water park • Tennis courts

How to Get to Windward Cay

Windward Cay is located 4.2 mi (6.8 km) from the heart of Kissimmee.

Flying to:

• • Orlando Intl. 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 See near Windward Cay:

• • Kissimmee Lakefront Park (4.4 mi/7 km away)
• • Lake Bryan (4.3 mi/6.9 km away)
• • Kissimmee Civic Center (4.3 mi/6.9 km away)
• • Osceola Performing Arts Center (4.8 mi/7.7 km away)
• • Shingle Creek Regional Park (1.3 mi/2 km away)

Things to Do near Windward Cay:

• • Old Town (3 mi/4.8 km away)
• • Disney Springs® (5 mi/8 km away)
• • Medieval Times (0.7 mi/1.1 km away)
• • Give Kids the World Village (1.7 mi/2.7 km away)
• • Fun Spot America (2.9 mi/4.7 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)