Find hotels in Windward Cay, Orlando from ₩44,937

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Discover 53,972 Windward Cay hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Seasons Florida Resort
Interior
Seasons Florida Resort
2.0 star property
8.8 out of 10, Excellent, (1846)
"Have stayed her many times and will stay here many more. The staff is always nice and accommodating. The rooms are always clean. Convenient to theme parks. GPS takes you to the side gate that is always closed. Turn off the main road by Capones. "
The price is ₩81,924
₩92,983 total
includes taxes & fees
May 31 - Jun 1
Seasons Florida Resort
Econo Lodge Inn & Suites Maingate Central
Lobby
Econo Lodge Inn & Suites Maingate Central
2.5 star property
5.8 out of 10, (1003)
"Better in pics. Need to be updatr"
The price is ₩45,959
₩71,195 total
includes taxes & fees
May 29 - May 30
Econo Lodge Inn & Suites Maingate Central
Club Sevilla
Property entrance
Club Sevilla
2.0 star property
8.8 out of 10, Excellent, (1001)
"Exelente lugar "
The price is ₩64,003
₩79,762 total
includes taxes & fees
May 16 - May 17
Club Sevilla
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Park Royal Orlando
Exterior
Park Royal Orlando
2.5 star property
7.8 out of 10, Good, (1001)
"The property has been going thru renovations, and although they have a little more to do ( example- check in motel Lobby building) The reviews I read online were very accurate The property is a great place to stay, rooms were great, beds newer, comfy, etc. stayed here because of the great ratings, given, it did not disappoint. Compared to other property’s in Kissimmee and Orlando, with their issue’s worth the extra drive to go a bit further for the peace of mind. The area, and business’s in ...
The price is ₩78,981
₩89,643 total
includes taxes & fees
Jun 4 - Jun 5
Park Royal Orlando
Vivo Flex Living Kissimmee
Standard Room, 2 Queen Beds, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets
Vivo Flex Living Kissimmee
2.5 star property
6.8 out of 10, (1000)
"Small property. Nice and quiet at night. But after a certain hour no staff are on property. Don’t have any issues. But if I did not sure how long it would take for them to show up"
The price is ₩98,518
₩111,818 total
includes taxes & fees
May 21 - May 22
Vivo Flex Living Kissimmee
Ambassador Inn
Outdoor pool
Ambassador Inn
2.0 star property
4.4 out of 10, (710)
"Great place"
The price is ₩49,957
₩87,016 total
includes taxes & fees
May 16 - May 17
Ambassador Inn
Sevilla Inn - Near Medieval Times
Front of property - evening/night
Sevilla Inn - Near Medieval Times
2.0 star property
5.6 out of 10, (825)
"It was an extremely nice room every thing was kept very well. I would stay there again. "
The price is ₩95,781
₩108,711 total
includes taxes & fees
May 23 - May 24
Sevilla Inn - Near Medieval Times
Red Carpet Inn
Lobby
Red Carpet Inn
2.5 star property
4.2 out of 10, (571)
"Staff is rude!"
The price is ₩44,937
₩79,749 total
includes taxes & fees
May 29 - May 30
Red Carpet Inn
RW Hotel
Outdoor pool
RW Hotel
2.5 star property
6.4 out of 10, (158)
"I loved it"
The price is ₩88,940
₩100,954 total
includes taxes & fees
Jun 12 - Jun 13
RW Hotel
Family Vacation Home, Water Park, Endless Resort Amenities
Exterior
Family Vacation Home, Water Park, Endless Resort Amenities
5.0 star property
9.0 out of 10, Wonderful, (24)
"My entire family enjoyed our stay. The unit was spacious, comfortable, clean, and well equipped. The resort amenities kept the kids busy. The resort staff and security were friendly and helpful."
Family Vacation Home, Water Park, Endless Resort Amenities
Sunshine Inn
Lobby
Sunshine Inn
2.0 star property
7.4 out of 10, Good, (137)
"The room was clean lovely and my stay was so comfortable."
The price is ₩82,143
₩93,232 total
includes taxes & fees
May 19 - May 20
Sunshine Inn
Knights Inn Kissimmee
Lobby
Knights Inn Kissimmee
2.0 star property
4.8 out of 10, (328)
"I was in town due to a death in the family. This little hotel was a nice break from the tasks at hand. The staff were very nice, always polite and accommodating. They had the coolest cat who I bought treats for. The room was a bit older and weathered, but it was comfortable and clean. A nice quiet retreat after my days of work. Thank you. "
The price is ₩272,292
₩321,510 total
includes taxes & fees
May 24 - May 25
Knights Inn Kissimmee
Days Inn by Wyndham Kissimmee West
Exterior
Days Inn by Wyndham Kissimmee West
2.5 star property
6.0 out of 10, (1001)
"Excellent hotel"
The price is ₩88,988
₩101,001 total
includes taxes & fees
Jun 4 - Jun 5
Days Inn by Wyndham Kissimmee West
Gorgeous New Home With Private Pool Within Minutes to Disney and Most Attractions
Villa | 4 bedrooms
Gorgeous New Home With Private Pool Within Minutes to Disney and Most Attractions
4.0 star property
10.0 out of 10, Exceptional, (1)
"Property was excellent for a family vacation. More then enough space for everyone, and was very clean. Not only was the property perfect but Adriana was an amazing host. She was very prompt with her responses and contacted me before, and during my stay to ensure I did not need anything. Would highly recommend. "
Gorgeous New Home With Private Pool Within Minutes to Disney and Most Attractions
Seven Dwarfs Vacations Resort
Front of property - evening/night
Seven Dwarfs Vacations Resort
2.5 star property
7.4 out of 10, Good, (15)
"I loved everything about my experience! Mrs Linda is so kind and motherly. She was very prompt with every phone conversation. My family and I will most definitely stay again! "
Seven Dwarfs Vacations Resort
Bella Vida Resort
ACO Bella Vida Resort 5 Bedroom Vacation Home with Pool (1870) | Living room | TV
Bella Vida Resort
3.5 star property
7.2 out of 10, Good, (73)
"Very Clean. Nice and quiet area. Comfortable living accommodations"
Bella Vida Resort
Near Theme Parks! Gorgeous 3 BR Town Home, Splash Park, Pool, Lake, And More!
Front of property
Near Theme Parks! Gorgeous 3 BR Town Home, Splash Park, Pool, Lake, And More!
3.5 star property
10.0 out of 10, Exceptional, (7)
"Large bedrooms. Beautiful property with excellent amenities. "
Near Theme Parks! Gorgeous 3 BR Town Home, Splash Park, Pool, Lake, And More!
Rodeway Inn Maingate Central
Outdoor pool
Rodeway Inn Maingate Central
2.0 star property
5.6 out of 10, (877)
"Very nice room; close to everything. My only complaint is the homeless people hanging around."
The price is ₩73,875
₩98,901 total
includes taxes & fees
May 23 - May 24
Rodeway Inn Maingate Central
Sonoma Resort
Outdoor pool, sun loungers
Sonoma Resort
3.5 star property
7.6 out of 10, Good, (18)
"I didn't take pictures as I thought it was a good price, even though the home we were assigned was in poor condition. The carpets were stained everywhere, the dining room table had areas severely damaged (and covered by a pretty cutting board), the chairs were stained, and the beds were super uncomfortable (and squeaked badly). The worst part was that the home had german roaches. We kept all food (snacks) in the fridge so the bugs could not get to it. Was disappointed but the pool made up for...
Sonoma Resort
Luxurious Family-friendly 5 Bd 12 Guests w Screened Pool Close to Disney
Apartment | 5 bedrooms, soundproofing, Internet
Luxurious Family-friendly 5 Bd 12 Guests w Screened Pool Close to Disney
3.0 star property
8.0 out of 10, Very Good, (2)
"Overall it was a decent vacation rental. The annoying parts were the complex check in process for both the property check in and then check in when driving up to the gate. For the check in process, it was a bit more annoying then the typical hotel check in. You have to go through another 5 steps at another website/system, almost had the property cancel on me on the day of check in because of missing documentation. The deposit is also annoying, they had extra charges so I had to call to get that...
Luxurious Family-friendly 5 Bd 12 Guests w Screened Pool Close to Disney
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See all available properties in Windward Cay
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.

Frequently asked questions

What's it like in Windward Cay?

Travelers to the Windward Cay neighborhood in Kissimmee will be sure to enjoy their stay.

What's a favorite place to stay in Windward Cay?

For your stay in Windward Cay, Windward Cay 4707 is one of the top choices based on our traveler data. Another good option for your stay in the area is Peaceful Windward Cay 3 Bedroom Home by Redawning.

How many hotels will I find in Windward Cay?

Expedia has 33 hotels and other accommodations in Windward Cay to choose from, making this an ideal home base for exploring the greater Kissimmee area.

If I need to cancel my hotel reservation in Windward Cay, will I receive a refund?

Yes, most hotel reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best deals available in Windward Cay.

Where can I learn more about changing or cancelling my trip to Windward Cay?

For more information about changing or cancelling your trip to Windward Cay, click here.

What is there to do around this Kissimmee neighborhood?

A few places to visit in the area around Windward Cay include Old Town, Medieval Times, and Kissimmee Go-Karts. While you're out sightseeing, Capone's Dinner Show and Pirate's Island Adventure Golf are a couple of additional sights to visit in Kissimmee.