Title: Windward Cay 2209 Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=7927&destination=Kissimmee%2C+Florida%2C+United+States+of+America&selected=36477030&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Windward Cay 2209 - Overview - Rooms - Location - Policies Windward Cay 2209 provides an arcade/games room and more. ## Popular amenities - Pool - Kitchen ## Check prices for these days [Tonight ](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [Tomorrow ](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-08&endDate=2026-04-09&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-08&endDate=2026-04-09&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [This weekend ](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-10&endDate=2026-04-12&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-10&endDate=2026-04-12&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [Next weekend ](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-17&endDate=2026-04-19&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-17&endDate=2026-04-19&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2) ## Room options ## You may also like Ad ![Exterior](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/2000000/1070000/1069000/1068973/ce207033_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Vacation Village Orlando, Celebration Kissimmee - Pool - Hot tub - Washing machine - Dryer 8.6 Excellent 3,821 reviews £95 includes taxes & fees 21 Apr - 22 Apr [](https://www.expedia.co.uk/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.Hotel-Information?chkin=2026-4-21&chkout=2026-4-22&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) Ad ![6 outdoor pools, free pool cabanas, pool umbrellas](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/1000000/30000/23200/23110/ade3b60d_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando Orlando - Pool - Hot tub - Kitchen - Washing machine 9.2 Wonderful 5,110 reviews £98 includes taxes & fees 5 May - 6 May [](https://www.expedia.co.uk/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information?chkin=2026-5-5&chkout=2026-5-6&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) Ad ![Property entrance](https://images.trvl-media.com/lodging/1000000/90000/84700/84682/47b4a2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Galleria Palms Hotel Kissimmee - Pool - Breakfast included - Parking included - Free Wi-Fi 9.0 Wonderful 3,640 reviews £84 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Orlando-Hotels-Galleria-Palms-Hotel.h84682.Hotel-Information?chkin=2026-4-13&chkout=2026-4-14&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) Ad ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/9600/9577/588f352f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Hilton Orlando/Altamonte Springs Altamonte Springs - Pool - Hot tub - Parking included - Free Wi-Fi 9.0 Wonderful 1,352 reviews £116 includes taxes & fees 12 Apr - 13 Apr [](https://www.expedia.co.uk/Orlando-Hotels-Hilton-OrlandoAltamonte-Springs.h9577.Hotel-Information?chkin=2026-4-12&chkout=2026-4-13&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) Ad ![5 outdoor pools, free pool cabanas, pool umbrellas](https://a.travel-assets.com/media/meso_cm/PAPI/Images/hotels/1000000/540000/539500/539487/1b1c7050_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando International Drive District - Pool - Hot tub - Washing machine - Dryer 9.2 Wonderful 3,258 reviews £92 includes taxes & fees 5 May - 6 May [](https://www.expedia.co.uk/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information?chkin=2026-5-5&chkout=2026-5-6&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) Ad ![Outdoor pool, pool loungers](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/1000000/910000/907700/907618/b94b1c8f_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Best Western Plus Orlando Lake Buena Vista South Inn & Suites Kissimmee - Pool - Hot tub - Breakfast included - Free Wi-Fi 8.0 Very good 1,473 reviews £81 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Orlando-Hotels-Best-Western-Plus-Kissimmee-Lake-Buena-Vista-South-Inn-Suites.h907618.Hotel-Information?chkin=2026-4-13&chkout=2026-4-14&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) Ad ![Outdoor pool, pool umbrellas, pool loungers](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/1000000/10000/7700/7622/41854f3a_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Radisson Hotel Orlando Lake Buena Vista South Kissimmee - Pool - Hot tub - Pet-friendly - Water slide 8.8 Excellent 4,233 reviews £91 includes taxes & fees 28 Apr - 29 Apr [](https://www.expedia.co.uk/Orlando-Hotels-Red-Lion-Hotel-Orlando-Lake-Buena-Vista-South.h7622.Hotel-Information?chkin=2026-4-28&chkout=2026-4-29&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) Ad ![Terrace/patio](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/1000000/700000/692700/692651/99fa078d_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Parkway International Resort Kissimmee - Pool - Hot tub - Kids’ pool - Parking included 9.4 Exceptional 2,269 reviews £128 includes taxes & fees 5 May - 6 May [](https://www.expedia.co.uk/Orlando-Hotels-Parkway-International-Resort.h692651.Hotel-Information?chkin=2026-5-5&chkout=2026-5-6&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) Ad ![Lobby](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/1000000/880000/874700/874635/0b917cab_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Hilton Vacation Club Polynesian Isles Kissimmee Kissimmee - Pool - Parking included - Free Wi-Fi - Air-conditioning 9.6 Exceptional 1,930 reviews £90 includes taxes & fees 4 May - 5 May [](https://www.expedia.co.uk/Orlando-Hotels-Polynesian-Isles-Resort.h874635.Hotel-Information?chkin=2026-5-4&chkout=2026-5-5&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) Ad ![Property grounds](https://images.trvl-media.com/lodging/66000000/65370000/65361000/65360948/46e1aea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### SPOT X Hotel Orlando/Intl Dr by The Red Collection Orlando - Pool - Breakfast included - Pet-friendly - Parking included 8.6 Excellent 3,245 reviews £75 includes taxes & fees 21 Apr - 22 Apr [](https://www.expedia.co.uk/Orlando-Hotels-SpotX-Hotel.h65360948.Hotel-Information?chkin=2026-4-21&chkout=2026-4-22&rm1=a2®ionId=178294&destination=Orlando (and vicinity)&destType=MARKET&latLong=28.54129,-81.37904&searchId=1445cda0-393c-4ae0-bc6a-abc5adf50ae6&top_cur=GBP) ![Mod logo](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Sign in to view eligible discounts and perks. More rewards for more adventures! [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 Windward Cay, a neighbourhood 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®. Orange County Convention Center and Epcot® are not to be missed. [Visit our Kissimmee travel guide](https://www.expedia.co.uk/Kissimmee.dx7927) [View more Holiday homes in Orlando](https://www.expedia.co.uk/Orlando-Private-Holiday-Homes.d178294-aaPrivateHolidayHomes.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 - ![Kissimmee_MedievalTimes_6153643_01](https://images.trvl-media.com/place/6153643/a52365ab-9f34-49ed-82c3-f0710fabf038.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Medieval Times 15 min walk \- 0.8 miles - ![Kissimmee_192FleaMarket_6239152_06](https://images.trvl-media.com/place/6239152/450f5ffa-50f1-403b-a77e-8e27ae531e81.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) 192 Flea Market 4 min drive \- 1.7 miles - Kissimmee Go-Karts 16 min walk \- 0.9 miles - Capone's Dinner Show 3 min drive \- 1.3 miles - Shingle Creek Regional Park 4 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 - Chick-fil-A 4 min drive - Steak 'n Shake 5 min drive - Wendy's 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 ![House, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/108000000/107560000/107550500/107550401/7570329c.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=2026-04-21&endDate=2026-04-22&selected=107550401&PinnedHotelID=107550401&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, dining tables](https://images.trvl-media.com/lodging/124000000/123260000/123254900/123254899/987a639c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Landing | Spectacular 2BD, Yoga Studio Kissimmee - Kitchen - Washing machine - Air-conditioning [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22&selected=123254899&PinnedHotelID=123254899&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, dining tables](https://images.trvl-media.com/lodging/124000000/123260000/123254900/123254869/fdcf67bf.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Landing | Modern 2BD, Yoga Studio Kissimmee - Kitchen - Washing machine - Air-conditioning [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22&selected=123254869&PinnedHotelID=123254869&HadPinnedHotel=true®ionId=-1&adults=2) ![TV](https://images.trvl-media.com/lodging/88000000/87740000/87739100/87739004/67b507a1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful pool home 20 minutes from Disney! 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Windward Cay - Pool - Kitchen - Washing machine - Dryer 10 Exceptional 4 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22&selected=122047035&PinnedHotelID=122047035&HadPinnedHotel=true®ionId=-1&adults=2) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111370000/111366900/111366836/b9bb7c2a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cozy studio in Kissimmee Windward Cay - Air-conditioning 10 Exceptional 1 review £104 includes taxes & fees 28 Apr - 29 Apr [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-28&endDate=2026-04-29&selected=111366836&PinnedHotelID=111366836&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/75000000/74630000/74627200/74627141/fe817116.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=2026-04-21&endDate=2026-04-22&selected=74627141&PinnedHotelID=74627141&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=2026-04-21&endDate=2026-04-22&selected=34985488&PinnedHotelID=34985488&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106330000/106329900/106329806/dde46b5a.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 10 Exceptional 1 review [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22&selected=106329806&PinnedHotelID=106329806&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22&selected=36477030&PinnedHotelID=36477030&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=36477030,107550401,123254899,123254869,87739004) ## 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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