[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Your Family will love the 1st Class Amenities at Your Private Villa on Windsor Island Resort Villa in Kissimmee with a fitness center and a hot tub ![Interior](https://images.trvl-media.com/lodging/66000000/65270000/65266000/65265972/fe54a354.jpg?impolicy=resizecrop&rw=598&ra=fit) ![A heated pool](https://images.trvl-media.com/lodging/66000000/65270000/65266000/65265972/fe42d1ea.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV, video games](https://images.trvl-media.com/lodging/66000000/65270000/65266000/65265972/2db891a0.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Game room](https://images.trvl-media.com/lodging/66000000/65270000/65266000/65265972/69862f7e.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor dining](https://images.trvl-media.com/lodging/66000000/65270000/65266000/65265972/d52bf6cf.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Escape to Orlando Villa 5044 at Windsor Island, Kissimmee's luxurious resort community. Enjoy a drink and meal at the tiki bar, lounge by the huge resort-style pool with cabanas and lazy river or stay active in the fitness center with state-of-the-art equipment. ### Entire home 7 bedrooms6 bathroomsSleeps 18 ## Popular amenities - Parking available - Air conditioning - Dryer - Outdoor space - Hot tub - Gym ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Your Family will love the 1st Class Amenities at Your Private Villa on Windsor Island Resort 5 Star Villa Holidays is proud to present Orlando Villa 5044 Windsor Island is Kissimmee’s newest and most luxurious resort community. This stunning vacation rental community features all the popular resort amenities of its sister communities - Windsor Hills Resort and Windsor Palms Resort, AND so much more! An extraordinary 5,000 sq.ft. clubhouse is the centerpiece, as well as a huge resort-style pool, complete with cabanas, a water slide, and lazy river – perfect for families to enjoy for hours! When it’s time for a drink or a bite to eat, the tiki bar serves both your favorite libation, along with a tempting menu for poolside dining. With all the latest in cardio and strength building equipment, the fitness center will keep you in shape while on vacation. For some friendly competition, there are sand volleyball courts and a multi-purpose sports courts. In addition, a sundry shop is located in the clubhouse, along with a video arcade. Windsor at Westside is a gated community, with an attendant, to ensure the safety for all our visiting guests.Windsor at Westside Resort is strategically located in the Kissimmee area, with easy access to the theme parks, dining and shopping. For those who are visiting Disney, the location provides quick access to all the Disney parks, via just one exit up Toll Road 429 to the Western Way Blvd. Disney entrance. Access to this “secret” west Disney entrance is just 8 minutes away and avoids the heavy traffic that can occur with the main Disney entrance.There is no better way to vacation than a rental home, and Windsor at Westside is sure to impress! ## Property amenities ### Pool/Spa - Heated pool - Hot tub - Private pool ### Internet - Available in the villa: Internet access ### Parking and transportation - Parking on site ### Food and drink - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Bedrooms - 7 bedrooms - Bedsheets provided ### Bathroom - 6 bathrooms - Hair dryer - Towels provided ### Living spaces - Living room ### Entertainment - Games - TV with cable/satellite channels - Video games ### Outdoor areas - Patio ### Laundry - Dryer - Laundry facilities ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking. - Wheelchair accessibility - Smoking not allowed ### Services and conveniences - Housekeeping (on request) - Iron/ironing board ### Things to do - Billiards/pool table - Gym - Heated pool ### Safety features - Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector) - Smoke detector not reported (host has not indicated whether there is a smoke detector on the property) ### General - Gated community - Housekeeping (on request) ## Similar properties ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120430000/120420300/120420277/c6c757f4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Solara Themed 6BR Near Disney Pool SummerKitchen Kissimmee - Pool - Washer - Dryer - Pet-friendly [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=120420277&PinnedHotelID=120420277&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350019/w1200h797x0y3-0a9b128e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 7901 Luxury Retreat 3BR Villa w/ Pool & Game! Reunion - Pool - Kitchen - Dryer - Pet-friendly [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=119350019&PinnedHotelID=119350019&HadPinnedHotel=true®ionId=-1&adults=2) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118330000/118327500/118327483/e4cafe3b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Enchanted Dreams Kissimmee - Pool - Kitchen - Parking included - Free WiFi 8.0 Very good 4 reviews CA $96 CA $205 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-22&endDate=2025-10-23&selected=118327483&PinnedHotelID=118327483&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/119000000/118100000/118092200/118092178/aa4dcf17.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Amazing 6 bedrooms with pool Liberty Village - Pool - Kitchen - Dryer - Air conditioning [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=118092178&PinnedHotelID=118092178&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109060000/109052500/109052490/1572c5d0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 7/6.5 Beautiful Vacation home with private pool, and much more!! Seasons - Pool - Hot tub - Kitchen - Washer 8.4 Very good 8 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=109052490&PinnedHotelID=109052490&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/102000000/101650000/101644800/101644738/ba7cf32f.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 10BD Bella Vida Modern House Near Parks (BV 4460) Kissimmee - Pool - Kitchen - Dryer - Air conditioning 8.8 Excellent 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=101644738&PinnedHotelID=101644738&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool](https://images.trvl-media.com/lodging/84000000/83460000/83458500/83458471/w507h683x259y0-2e589a2b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### DISNEY R US! UNIVERSAL IS TOO!!! Crestwynd Bay - Pool - Kitchen - Washer - Dryer 9.0 Wonderful 9 reviews CA $136 CA $404 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28&selected=83458471&PinnedHotelID=83458471&HadPinnedHotel=true®ionId=-1&adults=2) ![Game room](https://images.trvl-media.com/lodging/83000000/82350000/82343900/82343888/465fe057.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### FUN!-2Theaters-2 Game Rooms-Themed BRs-Pool/Spa Champions Gate - Pool - Hot tub - Kitchen - Washer 9.8 Exceptional 57 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=82343888&PinnedHotelID=82343888&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/44000000/44000000/43994900/43994823/8c390945.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Modern 6 Bed Villa Close to Parks, Orlando Villa 3212 Solterra Resort - Pool - Hot tub - Dryer - Air conditioning [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=43994823&PinnedHotelID=43994823&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/39000000/38720000/38715000/38714968/c3db29c0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Brand New 6BR house fully equipped with a heated pool located near Disney!!! Solterra Resort - Pool - Hot tub - Kitchen - Washer 8.6 Excellent 68 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-04&endDate=2025-11-05&selected=38714968&PinnedHotelID=38714968&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM ### Check-out Check-out before 10:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## 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 Onsite parties or group events are strictly prohibited 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 This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as 1613408148 Villa ## About the area Kissimmee is home to this villa. 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 Disney's Typhoon Lagoon Water Park and Walt Disney World® Resort. Disney's Hollywood Studios® and Epcot® are not to be missed. [Visit our Kissimmee travel guide](https://www.expedia.ca/Kissimmee.dx7927) [View more Villas in Orlando](https://www.expedia.ca/Orlando-Villas.d178294-aaVillas.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%7C28.34049%2C-81.47815&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=QU1Rxu35c2kFz3DfevavgTAweEU=) Orlando, FL ### What's nearby - Old Town - 5 min drive - 4.6 km - Disney Springs™ - 6 min drive - 7.1 km - Orlando Vineland Premium Outlets - 6 min drive - 7.8 km - SeaWorld® Orlando - 10 min drive - 13.1 km - Epcot® - 10 min drive - 11.0 km ### Getting around - Poinciana Station - 13 min drive - Kissimmee Station - 16 min drive - Kissimmee, FL (ISM-Kissimmee Gateway) - 17 min drive ### Restaurants - ‪Wawa - ‬3 min drive - ‪Churromania - ‬3 min drive - ‪First Watch - ‬3 min drive - ‪Taco Bell - ‬14 min walk - ‪Starbucks - ‬3 min drive ## Frequently asked questions ### Is Your Family will love the 1st Class Amenities at Your Private Villa on Windsor Island Resort pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at Your Family will love the 1st Class Amenities at Your Private Villa on Windsor Island Resort? > Check-in begins at 4:00 PM. ### What time is check-out at Your Family will love the 1st Class Amenities at Your Private Villa on Windsor Island Resort? > Check-out is at 10:00 AM. ### Where is Your Family will love the 1st Class Amenities at Your Private Villa on Windsor Island Resort located? > Situated in Kissimmee, this villa is 1 mi (1.7 km) from Lake Cecile and 2.9 mi (4.6 km) from Old Town. Capone's Dinner Show and Kissimmee Go-Karts are also within 2 mi (3 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Expedia's Latest Trends ### Hotels > [Marriott's Grande Vista](https://www.expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) > > [Rosen Shingle Creek](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) > > [Hilton Grand Vacations Club Tuscany Village Orlando](https://www.expedia.ca/Orlando-Hotels-Hilton-Grand-Vacations-At-Tuscany-Village.h1080602.Hotel-Information) > > [Holiday Inn Resort Orlando Suites - Waterpark by IHG](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Suites-Waterpark.h281608.Hotel-Information) > > [JW Marriott Orlando Grande Lakes](https://www.expedia.ca/Orlando-Hotels-JW-Marriott-Orlando-Grande-Lakes.h897538.Hotel-Information) > > [Hilton Orlando Lake Buena Vista - Disney Springs® Area](https://www.expedia.ca/Orlando-Hotels-Hilton-Orlando-Lake-Buena-Vista-Disney-Springs-Area.h11652.Hotel-Information) > > [Hilton Grand Vacations Club SeaWorld® Orlando](https://www.expedia.ca/Orlando-Hotels-Hilton-Grand-Vacations-At-SeaWorld.h565266.Hotel-Information) > > [Holiday Inn Resort Orlando - Lake Buena Vista by IHG](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.Hotel-Information) > > [Hilton Orlando Buena Vista Palace - Disney Springs® Area](https://www.expedia.ca/Orlando-Hotels-Hilton-Orlando-Buena-Vista-Palace-Disney-Springs-Area.h18591.Hotel-Information) > > [Hyatt Regency Orlando International Airport](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando-International-Airport.h2754.Hotel-Information) > > [CoCo Key Hotel and Water Resort](https://www.expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information)  > > [Lake Buena Vista Resort Village & Spa](https://www.expedia.ca/Orlando-Hotels-Lake-Buena-Vista-Resort-Village-Spa.h1350864.Hotel-Information) > > [Sheraton Orlando Lake Buena Vista Resort](https://www.expedia.ca/Orlando-Hotels-Sheraton-Orlando-Lake-Buena-Vista-Resort.h11993.Hotel-Information) > > [Wyndham Lake Buena Vista – Disney Springs® Area](https://www.expedia.ca/Orlando-Hotels-Wyndham-Lake-Buena-Vista-Disney-Springs-Resort-Area.h19384.Hotel-Information) > > [Marriott's Cypress Harbour Villas](https://www.expedia.ca/Orlando-Hotels-Marriotts-Cypress-Harbour-Villas.h57585.Hotel-Information) > > [Holiday Inn Orlando - Disney Springs® Area by IHG](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Orlando-Disney-Springs-Area.h16367.Hotel-Information) > > [Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://www.expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) > > [Wyndham Grand Orlando Resort Bonnet Creek](https://www.expedia.ca/Orlando-Hotels-Wyndham-Grand-Orlando-Resort-Bonnet-Creek.h4408039.Hotel-Information) > > [Hyatt Regency Grand Cypress](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Grand-Cypress.h24798.Hotel-Information) > > [Signia by Hilton Orlando - An Official Walt Disney World® Hotel](https://www.expedia.ca/Orlando-Hotels-Signia-By-Hilton-Orlando-Bonnet-Creek.h2455364.Hotel-Information) > > [Orlando World Center Marriott](https://www.expedia.ca/Orlando-Hotels-Orlando-World-Center-Marriott.h11312.Hotel-Information) > > [Courtyard Orlando Lake Buena Vista in the Marriott Village](https://www.expedia.ca/Orlando-Hotels-Courtyard-Orlando-Lake-Buena-Vista-In-The-Marriott-Village.h470830.Hotel-Information) > > [Meliá Orlando Celebration](https://www.expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) > > [Club Wyndham Bonnet Creek](https://www.expedia.ca/Orlando-Hotels-Club-Wyndham-Bonnet-Creek.h1547308.Hotel-Information) > > [Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://www.expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) > > [Drury Plaza Hotel Orlando - Disney Springs Area](https://www.expedia.ca/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.Hotel-Information) > > [Westgate Lakes Resort & Spa Universal Studios Area](https://www.expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) > > [Delta Hotels by Marriott Orlando Lake Buena Vista](https://www.expedia.ca/Orlando-Hotels-Delta-Hotels-By-Marriott-Orlando-Lake-Buena-Vista.h2690.Hotel-Information) > > [Caribe Royale Orlando](https://www.expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) > > [Hyatt Regency Orlando](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information)