Hotels in Windward Cay

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
Aug 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 22 - Aug 24
Next weekend
Aug 29 - Aug 31

Where to stay in Windward Cay?

Club Sevilla
Property entrance

Club Sevilla

2.0 star property
9.0 out of 10, Wonderful, (1004)
$55 nightly
The price is $68
Aug 22 - Aug 23
Total includes taxes and fees
Club Sevilla
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.
trending_down

Our prices for Kissimmee are cheapest in May

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 August

Month selector

Currently viewing crowd sizes and weather for August.
Weather forecast for Kissimmee
August
trending_downLow crowds
High 90°F / low 77°F. Partly sunny.
View properties in August
90°
weather_partly_sunny
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°
weather_sun
November, Low crowds, average high temperature 76 degrees Fahrenheit, average low temperature 62 degrees Fahrenheit. Sunny most days.
62°
73°
weather_sun
December, High crowds, average high temperature 73 degrees Fahrenheit, average low temperature 57 degrees Fahrenheit. Sunny most days.
57°
69°
weather_sun
January, Moderate crowds, average high temperature 69 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
53°
74°
weather_sun
February, High crowds, average high temperature 74 degrees Fahrenheit, average low temperature 57 degrees Fahrenheit. Sunny most days.
57°
78°
weather_sun
March, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
59°
82°
weather_sun
April, Moderate crowds, average high temperature 82 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
65°
86°
weather_sun
May, Low crowds, average high temperature 86 degrees Fahrenheit, average low temperature 69 degrees Fahrenheit. Sunny most days.
69°
88°
weather_sun
June, Moderate crowds, average high temperature 88 degrees Fahrenheit, average low temperature 74 degrees Fahrenheit. Sunny most days.
74°
90°
weather_sun
July, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 76 degrees Fahrenheit. Sunny most days.
76°
Monthly weather averages (˚F)

Top landmarks in Kissimmee

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.

See properties in Old Town
Old Town

Check out reviews of Windward Cay hotels guests love

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Clean and well kept hotel. Rooms are spacious. Wonderful breakfast options and very helpful and nice staff. The location is very convenient, with numerous dining options working walking and distance. There is also a small Target and Walgreens that you can walk to. We had a great stay."
Tayrin Yi 7-night trip
Posted 5 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Frequently asked questions

Is Windward Cay expensive to stay in?
You can find great hotels from $60 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.
How can I find discounted rates and deals for Windward Cay hotels?
Unlocking discounted rates at hotels in Windward Cay couldn't be simpler. Members save up to 20% on select hotels when signed in. Silver, Gold, and Platinum members can earn additional rewards on VIP Access bookings.
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".
What are some of the best pet-friendly hotels in Windward Cay?
Traveling with your pet doesn't mean sacrificing a great hotel stay. In Windward Cay, our travelers love:To find more pet-friendly stays on Hotels.com, use the "Amenities" filter in your search and select "Pet friendly".
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.
Are all taxes and fees included in the Windward Cay hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.
What are some of the best Windward Cay hotels with a pool?
Book a Windward Cay hotel with a pool for some added relaxation or exercise on your trip. For more Windward Cay hotels with a pool, use the "Amenities" filter in your search and select "Pool" on Hotels.com.
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 Bellavida and Lake Berkley.
What are some great hotels in Windward Cay with balconies?
There are some top hotels in Windward Cay that offer rooms with a balcony.
Are all taxes and fees included in the Windward Cay hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.

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)
  • Tupperware Center (4.9 mi/7.9 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)