Hotels in Windward Cay

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Tonight
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Where to stay in Windward Cay?

Seasons Florida Resort
Property grounds

Seasons Florida Resort

2.0 star property
8.8 out of 10, Excellent, (3158)
The price is $47
$54 total
includes taxes & fees
Sep 28 - Sep 29
Seasons Florida Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Our prices for Kissimmee are cheapest in September

See average prices and weather for all months
Price trends for hotels in Kissimmee
Pricing is based on two traveler single night rates
View properties in September
Currently viewing crowd sizes and weather for September.
Weather forecast for Kissimmee
September
trending_downLow crowds
High 31°C / low 24°C. Sunny most days.
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31°
weather_sun
September, Low crowds, average high temperature 31 degrees Celsius, average low temperature 24 degrees Celsius. Sunny most days.
24°
28°
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October, Moderate crowds, average high temperature 28 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
25°
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November, Low crowds, average high temperature 25 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
23°
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December, High crowds, average high temperature 23 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
21°
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January, Moderate crowds, average high temperature 21 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
23°
weather_sun
February, High crowds, average high temperature 23 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
25°
weather_sun
March, High crowds, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
28°
weather_sun
April, Moderate crowds, average high temperature 28 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
30°
weather_sun
May, Low crowds, average high temperature 30 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
31°
weather_sun
June, Moderate crowds, average high temperature 31 degrees Celsius, average low temperature 24 degrees Celsius. Sunny most days.
24°
32°
weather_sun
July, High crowds, average high temperature 32 degrees Celsius, average low temperature 25 degrees Celsius. Sunny most days.
25°
32°
weather_partly_sunny
August, Low crowds, average high temperature 32 degrees Celsius, average low temperature 25 degrees Celsius. Partly sunny.
25°
Monthly weather averages (˚C)

Top landmarks in Kissimmee

Old Town
caught in a torrential downpour while exploring Old Town but did get to see lots of the awesome classic cars that come out for the weekly Friday night car show - a busy tourist spot but a nice change from the neighboring Disney/Sea World/Universal parks

Old Town

Why not give yourself a treat with a trip to Old Town, one of the most popular family attractions located 7.1 mi (11.4 km) from central Kissimmee. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you have fun at Old Town, you'll love Fun Spot America, just a short walk away.

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Mystic Dunes Golf Club
Orlando which includes golf

Mystic Dunes Golf Club

You might want to play some rounds at Mystic Dunes Golf Club, located 2 mi (3.3 km) from central Four Corners. If Mystic Dunes Golf Club doesn't quite scratch your golfing itch, Reunion Resort Golf Course, and ChampionsGate Golf Club are also nearby.

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Check out reviews of Windward Cay hotels guests love

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent
"This hotel is perfectly located and gives access to Orlando."
Jose Alejandro 3-night trip
Posted 8 hours ago
DoubleTree by Hilton Hotel Orlando at SeaWorld

Find out more about Windward Cay

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. Disney Springs™ and Epcot® are a couple of the top places in the larger area worth a visit. Orange County Convention Center and Disney's Animal Kingdom® Theme Park are a couple of popular sights nearby.

How to Get to Windward Cay

Flying to:

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

Things to See and Do in and around Windward Cay

Things to See near Windward Cay:

  • Lake Bryan (4.3 mi/6.9 km away)
  • Lake Cecile (1.4 mi/2.2 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)
  • Corpus Christi Catholic Church (4.6 mi/7.4 km away)

Things to Do near Windward Cay:

  • Disney Springs™ (5 mi/8 km away)
  • Old Town (3 mi/4.8 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, February, December, March (average 64°F)
  • Rainiest months: August, July, September, June (average 8 inches of rainfall)

Keep exploring

Keep exploring