Title: Windward Cay 2209 Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Windward Cay 2209 Holiday home in Kissimmee with an outdoor pool - Overview - Rooms - Location - Policies Windward Cay 2209 provides an arcade/games room and more. ## Popular amenities - Pool - Kitchen ## Room options ### Check availability for these dates Tonight [Dec 31 - Jan 1](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-31&endDate=2026-01-01&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-31&endDate=2026-01-01&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Jan 1 - Jan 2](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-01&endDate=2026-01-02&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-01&endDate=2026-01-02&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Jan 2 - Jan 4](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-02&endDate=2026-01-04&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-02&endDate=2026-01-04&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Jan 9 - Jan 11](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-09&endDate=2026-01-11&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-09&endDate=2026-01-11&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) ## You may also like Ad ![4 outdoor pools, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/1000000/860000/853600/853519/w4000h2662x0y0-7b7256af_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Marriott's Grande Vista Orlando - Pool - Hot tub - Spa - Kids’ pool 9.0 Wonderful 3,744 reviews £100 includes taxes & fees 25 Jan - 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[Sign in](https://www.expedia.co.uk/login?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOrlando-Hotels-Windward-Cay-2209.h36477030.Hotel-Information)[Sign up, it's free](https://www.expedia.co.uk/signup?enable_registration=true&uurl=e3id%3Dredr%26rurl%3D%2FOrlando-Hotels-Windward-Cay-2209.h36477030.Hotel-Information) ## About the area ![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 \- 0.8 miles - Kissimmee Go-Karts \- 16 min walk \- 0.9 miles - Capone's Dinner Show \- 2 min drive \- 1.1 miles - Shingle Creek Regional Park \- 3 min drive \- 1.3 miles - 192 Flea Market \- 3 min drive \- 1.7 miles #### 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 - ‪Chipotle - ‬5 min drive - ‪Wendy's - ‬5 min drive - ‪Steak 'n Shake - ‬5 min drive ## About this property ### Windward Cay 2209 Holiday home near Old Town Windward Cay 2209 provides an arcade/games room and more. You'll also enjoy perks such as: - An outdoor pool - Barbecues Room features All guest rooms at Windward Cay 2209 include comforts, such as private pools, in addition to More conveniences in all rooms include: - TVs with cable channels ## Similar properties ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39960000/39952000/39951919/270-5acf9799.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 4 Bed Holiday in the heart of Kissimmee (Internet) Windward Cay - Pool - Kitchen - Washing machine - Dryer 9.4 Exceptional 8 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-14&endDate=2026-01-15&selected=39951919&PinnedHotelID=39951919&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/34000000/33980000/33976600/33976577/19b267b6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Splendid 3 Bed Villa in Windward Cay Windward Cay - Pool - Hot tub - Kitchen - Washing machine 10 Exceptional 24 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-14&endDate=2026-01-15&selected=33976577&PinnedHotelID=33976577&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/35000000/34990000/34985500/34985488/c32fff9a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cosy Kissimmee Pool Home w/Games Room in secluded community. Near Disney Windward Cay - Pool - Kitchen - Washing machine - Dryer 9.2 Wonderful 12 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-14&endDate=2026-01-15&selected=34985488&PinnedHotelID=34985488&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74630000/74627200/74627141/15e93cec.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Sunkissed Oasis 5 BR Home, Pool, Spa & Game Room in Windsor Palms Resort Windward Cay - Pool - Hot tub - Kitchen - Washing machine [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-14&endDate=2026-01-15&selected=74627141&PinnedHotelID=74627141&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35240000/35237300/35237299/792072f2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Florida Lets A Dream Windward Cay - Pool - Hot tub - Kitchen - Washing machine 9.6 Exceptional 32 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-14&endDate=2026-01-15&selected=35237299&PinnedHotelID=35237299&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/123000000/122050000/122047100/122047035/fe988392.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful 3 Bedroom Villa in Kissimmee – Your Florida Getaway Awaits! Windward Cay - Pool - Kitchen - Washing machine - Dryer [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-14&endDate=2026-01-15&selected=122047035&PinnedHotelID=122047035&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/88000000/87740000/87739100/87739004/c9768b55.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful pool home 20 minutes from Disney! Windward Cay - Pool - Hot tub - Kitchen - Air-conditioning 7.0 Good 4 reviews £244 includes taxes & fees 12 Jan - 13 Jan 2026 [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-12&endDate=2026-01-13&selected=87739004&PinnedHotelID=87739004&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106330000/106329900/106329806/39b894b4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Bright contemporary home, recently renovated, private south facing pool, movie room Windward Cay - Pool - Kitchen - Washing machine - Dryer [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-14&endDate=2026-01-15&selected=106329806&PinnedHotelID=106329806&HadPinnedHotel=true®ionId=-1&adults=2) ![House, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550401/cd54b112.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Stardust Villa 4 Bedroom Home by RedAwning Windward Cay - Washing machine - Parking included - Free Wi-Fi [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-14&endDate=2026-01-15&selected=107550401&PinnedHotelID=107550401&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/112000000/111370000/111366900/111366836/8e2bfbcf.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cozy studio in Kissimmee Windward Cay - Air-conditioning 10 Exceptional 1 review £106 includes taxes & fees 11 Jan - 12 Jan 2026 [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-11&endDate=2026-01-12&selected=111366836&PinnedHotelID=111366836&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 Information provided by the property may be translated using automated translation tools ### Access methods Access code ### Children and extra beds Children are welcome ### Payment types at the property ## Important information ### You need to know This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. 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 If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal. ### 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? ### What time is check-in at Windward Cay 2209? ### What time is check-out at Windward Cay 2209? ### Where is Windward Cay 2209 located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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