[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Windward Cay 2209 Vacation home in Kissimmee with an outdoor pool - Overview - Rooms - Location - Policies Windward Cay 2209 provides an arcade/game room and more. ## Popular amenities - Pool - Kitchen ## Room options ### Check availability for these dates Tonight [Oct. 7 - Oct. 8](https://www.expedia.ca/Hotel-Search?startDate=2025-10-07&endDate=2025-10-08&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-07&endDate=2025-10-08&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Oct. 8 - Oct. 9](https://www.expedia.ca/Hotel-Search?startDate=2025-10-08&endDate=2025-10-09&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-08&endDate=2025-10-09&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Oct. 10 - Oct. 12](https://www.expedia.ca/Hotel-Search?startDate=2025-10-10&endDate=2025-10-12&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-10&endDate=2025-10-12&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Oct. 17 - Oct. 19](https://www.expedia.ca/Hotel-Search?startDate=2025-10-17&endDate=2025-10-19&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-17&endDate=2025-10-19&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) ## You may also like Ad ![6 outdoor pools, cabanas (surcharge), pool umbrellas](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/2000000/1030000/1030000/1029950/04a753a5_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Omni Orlando Resort at ChampionsGate Champions Gate - Pool - Spa - Pet-friendly - Kids pool 9.0 Wonderful 1,004 reviews CA $264 CA $378 total includes taxes & fees Oct 10 - 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More rewards for more adventures! [Sign in](https://www.expedia.ca/login?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOrlando-Hotels-Windward-Cay-2209.h36477030.Hotel-Information)[Sign up, it's free](https://www.expedia.ca/signup?enable_registration=true&uurl=e3id%3Dredr%26rurl%3D%2FOrlando-Hotels-Windward-Cay-2209.h36477030.Hotel-Information) ## About the area Windward Cay, a neighborhood in Kissimmee, is home to Windward Cay 2209. Old Town and Disney Springs™ are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Hollywood Studios®. Epcot® and Disney's Animal Kingdom® Theme Park are not to be missed. [Visit our Kissimmee travel guide](https://www.expedia.ca/Kissimmee.dx7927) [View more Vacation homes in Orlando](https://www.expedia.ca/Orlando-Private-Vacation-Homes.d178294-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C28.31056%2C-81.47169&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=bJmn5GNogh9ho1ul1LDfA-oRP2U=) 2209 Chappell Court, Kissimmee, FL, 34746 ### What's nearby - Medieval Times - 15 min walk - 1.3 km - Kissimmee Go-Karts - 16 min walk - 1.3 km - Give Kids the World Village - 5 min drive - 3.7 km - Old Town - 9 min drive - 7.7 km - Disney Springs™ - 11 min drive - 11.5 km ### Getting around - Kissimmee Station - 10 min drive - Poinciana Station - 12 min drive - Kissimmee, FL (ISM-Kissimmee Gateway) - 12 min drive ### Restaurants - ‪Wawa - ‬4 min drive - ‪McDonald's - ‬4 min drive - ‪Medieval Times Dinner & Tournament - ‬3 min drive - ‪Wendy's - ‬5 min drive - ‪Steak 'n Shake - ‬5 min drive ## About this property ### Windward Cay 2209 Vacation home near Old Town Windward Cay 2209 provides an arcade/game room and more. You'll also enjoy perks such as: - An outdoor pool - Barbecue grills Room features All guestrooms at Windward Cay 2209 offer comforts such as private pools, in addition to amenities like internet access. More conveniences in all rooms include: - TVs with cable channels ## Policies ### Check-in Check-in start time: 4:00 PM; Check-in end time: 7:00 PM Minimum check-in age: 25 ### Check-out Check-out before 10:00 AM ### Special check-in instructions Guests will receive an access code ### Access methods Access code ### Children and extra beds Children are welcome ### Property payment types ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed This property accepts credit cards Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has not indicated whether there is a smoke detector on the property ### Property is also known as Windward Cay 2209 House Kissimmee Windward Cay 2209 House Windward Cay 2209 Kissimmee Private vacation home Windward Cay 2209 Kissimmee Kissimmee Windward Cay 2209 Private vacation home Private vacation home Windward Cay 2209 Windward Cay 2209 Kissimmee Windward Cay 2209 Private vacation home Windward Cay 2209 Private vacation home Kissimmee ## Frequently asked questions ### Does Windward Cay 2209 have a pool? > Yes, this property has an outdoor pool. ### What time is check-in at Windward Cay 2209? > Check-in start time: 4:00 PM; Check-in end time: 7:00 PM. ### What time is check-out at Windward Cay 2209? > Check-out is at 10:00 AM. ### Where is Windward Cay 2209 located? > Located in Windward Cay, this vacation home is within 2 mi (3 km) of Medieval Times, Kissimmee Go-Karts, and 192 Flea Market. Capone's Dinner Show and Give Kids the World Village are also within 3 mi (5 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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