Title: Book the Best Windermere LUXURY Hotels - Upscale Hotels in Windermere, FL | Expedia.ca [Hotels in Windermere](https://expedia.ca/Windermere-Hotels.d6085091.Travel-Guide-Hotels)[Vacation Rentals in Windermere](https://expedia.ca/Windermere-Vacation-Rentals.d6085091.Travel-Guide-VacationRentals)[Flights to Windermere](https://expedia.ca/Cheap-Flights-To-Windermere.d6085091.Travel-Guide-Flights)[Things to do in Windermere](https://expedia.ca/Things-To-Do-In-Windermere.d6085091.Travel-Guide-Activities)[Windermere Car Rentals](https://expedia.ca/Car-Rentals-In-Windermere.d6085091.Car-Rental-Guide)[Windermere Vacation Packages](https://expedia.ca/Windermere.d6085091.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/533000/533443-tibet-butler-preserve.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Windermere, FL - ![](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 Windermere Luxury Hotels Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-11-03&endDate=2025-11-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-11-04&endDate=2025-11-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Windermere Luxury Hotels ## Top Windermere Hotel Reviews ![Rosen Inn Lake Buena Vista](//images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 10/10 Excellent "The location was great the people were great. Will stay again " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Holiday Inn Resort Orlando - Lake Buena Vista by IHG](//images.trvl-media.com/lodging/1000000/20000/19600/19535/aa564e7f_y.jpg) ### Holiday Inn Resort Orlando - Lake Buena Vista by IHG 10/10 Excellent "Everything was wonderful. Staff was kind and caring, the place was clean with great amenities. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.Hotel-Information) ![Hilton Vacation Club Mystic Dunes Orlando](//images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg) ### Hilton Vacation Club Mystic Dunes Orlando 10/10 Excellent "clean, staff" [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![DoubleTree by Hilton Hotel Orlando at SeaWorld](//images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10/10 Excellent "Room service was excellent, room was clean and the view was amazing. " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](//images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "The staff was wonderful! We've been staying at this property for 20 years, never disappoints. Our home away from home when we take a quick trip to Orlando for a couple of days. Most comfortable beds in the world!" [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Hyatt Regency Orlando](//images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "All was good" [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) ![CoCo Key Hotel and Water Resort ](//images.trvl-media.com/lodging/1000000/10000/300/228/73a42af2_y.jpg) ### CoCo Key Hotel and Water Resort  10/10 Excellent "Friendly staff, clean and convenient. Great place for a family stay!" [](https://expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information)  ![Walt Disney World Dolphin](//images.trvl-media.com/lodging/1000000/20000/12800/12710/a6b6c49c_y.jpg) ### Walt Disney World Dolphin 10/10 Excellent "Everything was what I expected. Staff was extremely courteous and helpful. " [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information) ![Marriott's Grande Vista](//images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "Nice stay will book again " [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ## Frequently asked questions ### Which area of Windermere is best to stay in for luxury hotels? > The best area to stay in Windermere for luxury hotels is along the shores of Lake Butler, particularly in the vicinity of the Isleworth and Keene's Pointe communities. > > > > This area is known for its exclusive residential developments and offers a tranquil, upscale environment. You'll find properties that provide direct lake access and offer a high degree of privacy, often situated on spacious grounds. The main thoroughfares, like Conroy Road and Apopka Vineland Road, provide access to these more secluded luxury options. > > > > Couples seeking a sophisticated and quiet retreat will find this area particularly appealing. The focus here is on relaxation and enjoying the natural beauty of the Central Florida lakes, with opportunities for boating or simply unwinding by the water. The luxury hotels in this vicinity often feature amenities such as private dining experiences, expansive spa facilities, and high-end fitness equipment. > > > > Families looking for a premium holiday experience will also appreciate the larger, more private accommodations available. ### How much does a luxury hotel in Windermere cost? > Luxury hotel prices in Windermere vary, but you can find a great deal on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates. ### What luxury activities and experiences are there in Windermere? > The best area to stay for luxury activities and experiences in Windermere is generally within the gated communities and along the shores of the Butler Chain of Lakes. > > > > These areas are characterised by expansive, privately owned estates and exclusive resorts, many of which offer direct lake access. The community is generally quiet, with well-maintained streets and lush landscaping. While not a bustling town centre, the luxury experience here is about tranquility, privacy, and high-end amenities. > > > > Couples looking for a private and upscale retreat will find the lakeside properties particularly appealing. Many of these accommodations offer private docks, allowing for activities like boating, paddleboarding, or simply enjoying the serene lake views. Dining experiences often include private chef services or exclusive access to fine dining within resort properties. > > > > Families seeking a luxurious holiday will appreciate the spaciousness and amenities available in these exclusive communities. Properties often feature large private pools, dedicated entertainment rooms, and extensive grounds for relaxation and play. ### How can I save on a luxury hotel in Windermere with Expedia? > There are plenty of ways to save on a luxury hotel in Windermere. Unlock our lowest prices by joining [One Key™](https://www.expedia.ca/welcome-one-key), Expedia's travel rewards program. It's free and easy to sign up, and you can access member perks too. Typically, booking in advance will help you save on your luxury hotel booking. If you're feeling spontaneous, be sure to check for last-minute deals. ### Is it cheaper to book a luxury Windermere hotel and flights as a package? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect [travel package](https://www.expedia.ca/Windermere.d6085091.Destination-Travel-Guides). ### Can I cancel my luxury hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. 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