Title: Book the Best ROMANTIC Hotels in Windsor Hills, Orlando from CA $107 - Windsor Hills Romantic Getaways | Expedia.ca [Windsor Hills Travel Guide](https://expedia.ca/Orlando-Windsor-Hills.dx553248635976007891)[Vacation Rentals in Orlando](https://expedia.ca/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals)[Flights to Orlando](https://expedia.ca/Cheap-Flights-To-Orlando.d178294.Travel-Guide-Flights)[Things to do in Orlando](https://expedia.ca/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities)[Windsor Hills Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor-Hills.d553248635976007891.Car-Rental-Guide)[Windsor Hills Vacations](https://expedia.ca/Windsor-Hills.d553248635976007891.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Windsor Hills, Orlando from CA $107 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Windsor Hills Romantic Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-10-13&endDate=2025-10-14&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-10-14&endDate=2025-10-15&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976007891&startDate=2025-10-24&endDate=2025-10-26&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windsor Hills Romantic Hotels ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/59000000/58950000/58949700/58949619/15934269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/59000000/58950000/58949700/58949619/b8da5ab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/59000000/58950000/58949700/58949619/b0e3addc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/59000000/58950000/58949700/58949619/w1621h1077x0y0-f48c3645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Windsor Hills Mickey’s Dream Home, 2mi to Disney! Windsor Hills 10/10 Exceptional (14) "As advertised. Worked perfect for us and close to the parks. " CA $136 CA $422 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Orlando-Hotels-Luxury-Windsor-Hills-Mickeys-Dream-Home.h58949619.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/60000000/59200000/59197700/59197610/58f34ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/60000000/59200000/59197700/59197610/2b6d7ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59200000/59197700/59197610/951e784c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59200000/59197700/59197610/31627788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windsor Hills Resort/3Bedrm/2miles Disney Windsor Hills 9.6/10 Exceptional (19) "Perfect spot for our family vacation. " CA $136 CA $645 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Orlando-Hotels-Amazing-Disney-POOL-Villa-2-Miles-To-Disney-3bdr-Themed-RMS2-Miles-To-Disney.h59197610.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/50000000/49320000/49311000/49310927/df44d47a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis, books](https://images.trvl-media.com/lodging/50000000/49320000/49311000/49310927/963727f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/50000000/49320000/49311000/49310927/3daff013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49320000/49311000/49310927/d515e25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❤️Poolside TV, 3 Kings, FREE Waterpark, AC Game Rm Windsor Hills 10/10 Exceptional (44) "We were so impressed with the house! It was exactly as described. We made sure to keep it immaculate, so the next people who choose to stay there will enjoy it as much as we did. " CA $313 CA $816 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Orlando-Hotels-Livin-Free2WorkSchoolPlay-NEW.h49310927.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/57000000/56480000/56470700/56470671/84190951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/57000000/56480000/56470700/56470671/164e03a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/57000000/56480000/56470700/56470671/3459b778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/57000000/56480000/56470700/56470671/f2e90e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Livin Great❤️3 King Suites, FREE Resort, Private South Pool Windsor Hills 10/10 Exceptional (56) "We loved staying here. It was so close to Disney and really liked all of the amenities this place has. Got good use of the pool, waterpark , game room and more. Thank you Laura for everything! " CA $279 CA $719 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Orlando-Hotels-Livin-Great3-King-Suites.h56470671.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/39000000/38820000/38813700/38813700/429ceccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/39000000/38820000/38813700/38813700/w622h468x0y0-c1018fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38820000/38813700/38813700/8162c3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis, books, video library](https://images.trvl-media.com/lodging/39000000/38820000/38813700/38813700/20fa7776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❤️FREE Resort, 3 Kings, 4 Parking Spaces, AC Game Rm Windsor Hills 10/10 Exceptional (83) "Super easy, super convenient, clean house Awesome time " CA $314 CA $814 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Orlando-Hotels-Livin-Freenew-AC-Game-Rm.h38813700.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33560000/33556700/33556670/304ac834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33556700/33556670/a2b9a667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/34000000/33560000/33556700/33556670/ec3e4d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis, books, video library](https://images.trvl-media.com/lodging/34000000/33560000/33556700/33556670/fc59cb7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Livin the Dream❤️Closest FREE Resort to Disney! 3 Kings Windsor Hills 10/10 Exceptional (97) "The house was well priced for as big as it is and was clean and easy to get in and out of. The property manager was very responsive with any questions and giving any information needed for staying in the home and neighborhood. " CA $314 CA $819 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orlando-Hotels-Livin-The-Dreamclosest-Free-Resort-To-Disney-Pet-Friendly.h33556670.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/57000000/56480000/56470700/56470698/06a53322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/57000000/56480000/56470700/56470698/51304a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/57000000/56480000/56470700/56470698/23406e9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis, books](https://images.trvl-media.com/lodging/57000000/56480000/56470700/56470698/0179bd82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*NEW\*Theater, FREE Resort, 3 Kings, 2 mi WDW Windsor Hills 10/10 Exceptional (58) "Had a great stay! Laura was the perfect host. Kids loved the pool and we had a hard time getting them out of it. :) Beds and pillows were super comfy and theater room was a great addition. Would definitely stay there again. " CA $314 CA $819 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orlando-Hotels-Livin-The-MomentTheatre-FREE-Resort-WDW-2mi.h56470698.Hotel-Information) ![4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/cca9a672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/2ac14176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/89cab51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![11 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/a5c2174b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Shingle Creek Orlando 9.4/10 Exceptional (4087) "Always a great experience when we stay here. " CA $145 CA $163 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/6ba6ccf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 16.95 per person)](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/e8180b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/ee39e243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Kissimmee by the Parks by IHG Kissimmee 8.4/10 Very good (787) "Awesome place to stay" CA $73 CA $110 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/6be4ba41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/2d27f9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/ec5c4036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/59b49068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Orlando Lake Buena Vista Orlando 8.8/10 Excellent (1782) "Great stay " CA $95 CA $107 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28®ionId=553248635976007891&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Windsor Hills Hotel Reviews ## Frequently asked questions ### Searching for romantic hotels in Windsor Hills? > If you and your partner need a romantic escape, we've got just the ticket. If you want to get out and explore the larger area, you might head to Disney's Animal Kingdom® Theme Park, Epcot®, or Disney Springs™. If you're interested in staying close to a certain attraction, you can sort by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list. ### What is there to do in Windsor Hills? > There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Windsor Hills. There's plenty to see in the greater Four Corners area, so you might plan to visit Disney's Animal Kingdom® Theme Park, Epcot®, or Disney Springs™. ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Adults-Only-Resorts.0-0-d6048177-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Beach-Hotel.0-0-d6048177-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Boutique-Hotel.0-0-d6048177-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Business-Hotel.0-0-d6048177-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Central Florida](https://www.expedia.ca/Central-Florida-Hotels-Casino-Hotel.0-0-d6048177-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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