Hotels in Windward Cay

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Check prices for these dates

Tonight
Dec 20 - Dec 21
Tomorrow
Dec 21 - Dec 22
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4

Where to stay in Windward Cay?

Property grounds
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1 mi from Windward Cay
8.8 out of 10, Excellent, (3299)
$49 nightly
The price is $56
Jan 20 - Jan 21, 2026
Total with taxes and fees
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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When is the best time to visit Kissimmee?

Our prices for hotels in Kissimmee are cheapest in May
Price trends for hotels in Kissimmee
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Kissimmee
December
High crowds
High 73°F / low 57°F. Sunny most days.
View properties in December
73°
weather_sun
December, High crowds, average high temperature 73 degrees Fahrenheit, average low temperature 57 degrees Fahrenheit. Sunny most days.
57°
69°
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January, Moderate crowds, average high temperature 69 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
53°
74°
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February, High crowds, average high temperature 74 degrees Fahrenheit, average low temperature 57 degrees Fahrenheit. Sunny most days.
57°
78°
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March, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
59°
82°
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April, Moderate crowds, average high temperature 82 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
65°
86°
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May, Low crowds, average high temperature 86 degrees Fahrenheit, average low temperature 69 degrees Fahrenheit. Sunny most days.
69°
88°
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June, Moderate crowds, average high temperature 88 degrees Fahrenheit, average low temperature 74 degrees Fahrenheit. Sunny most days.
74°
90°
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July, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 76 degrees Fahrenheit. Sunny most days.
76°
90°
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August, Low crowds, average high temperature 90 degrees Fahrenheit, average low temperature 77 degrees Fahrenheit. Partly sunny.
77°
87°
weather_sun
September, Low crowds, average high temperature 87 degrees Fahrenheit, average low temperature 75 degrees Fahrenheit. Sunny most days.
75°
83°
weather_sun
October, Moderate crowds, average high temperature 83 degrees Fahrenheit, average low temperature 69 degrees Fahrenheit. Sunny most days.
69°
76°
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November, Low crowds, average high temperature 76 degrees Fahrenheit, average low temperature 62 degrees Fahrenheit. Sunny most days.
62°
Monthly weather averages (˚F)

Check out reviews of Windward Cay hotels guests love

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Nice location clean everything we needed. "
AMY 6-night trip
Posted 15 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Frequently asked questions

Is Windward Cay expensive to stay in?
You can find great hotels from $95 in Windward Cay to suit a range of budgets. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Windward Cay hotels?
Discover great deals on hotels in Windward Cay with Hotels.com. Sign up for free to unlock member only prices and start earning rewards. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Windward Cay hotels.
Can I receive a refund if I cancel my Windward Cay hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Windward Cay hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
Is it worth staying in Windward Cay?
You're spoilt for choice with 28 hotels in the area so it's easy to find your perfect somewhere. Basing yourself in Windward Cay makes it easy to explore Kissimmee, including the neighborhoods of International Drive District and Lake Berkley.
Find out more about Windward Cay

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