Title: Book the Best Winter Park LUXURY Hotels - Upscale Hotels in Winter Park, FL | Expedia.ca [Hotels in Winter Park](https://expedia.ca/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.ca/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.ca/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Winter Park Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.ca/Winter-Park.d7902.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/338000/338301-Casa-Feliz-Historic-Home-Museum.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Winter Park, FL ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winter Park Luxury Hotels Tonight [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-09-25&endDate=2025-09-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 26 - Sep 27](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-09-26&endDate=2025-09-27&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-09-26&endDate=2025-09-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winter Park Luxury Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/51fdc461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 10:00 AM to 5:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/w720h947x0y0-b237fd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/fcdf7880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/93bcae58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alfond Inn Winter Park 9.4/10 Exceptional (1008) "Wonderful location and excellent staff." CA $399 CA $488 total includes taxes & fees Sep 26 - Sep 27 [](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/21834885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/52e0ae75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/450d6e5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front Side Balcony Suite, 1 King](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/96b386a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Plaza Hotel Park Avenue District 8.6/10 Excellent (1002) "Park Plaza is a darling B&B style hotel just a short walk to virtually everything in Winter Park. The hotel staff was lovely and extremely helpful. " CA $203 CA $228 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Orlando-Hotels-Park-Plaza-Hotel.h1784873.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=2025-10-09&endDate=2025-10-10®ionId=7902&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Winter Park ### Winter Parkand its attractions for luxury travelers Winter Park, Florida, is a hidden gem for luxury travellers seeking a blend of culture, relaxation, and adventure. Begin your exploration at the Charles Hosmer Morse Museum of American Art, home to a stunning collection of Tiffany glass that captivates art enthusiasts and families alike. Just a short stroll away, the scenic Winter Park Scenic Boat Tour offers a unique perspective on the area's picturesque lakes and lush landscapes, perfect for leisurely afternoons. For those who enjoy retail therapy, Park Avenue boasts an array of upscale boutiques and gourmet dining options, where you can indulge in fine cuisine or simply sip a coffee while people-watching. If you're feeling active, the beautiful lawns of Central Park are ideal for a family picnic or a gentle stroll under the canopy of oak trees. Finally, the luxurious accommodations in this area, such as the Alfond Inn, provide opulent amenities and personalised service, creating a sanctuary after a day of adventure. Staying here allows you to enjoy the vibrant local culture while being pampered in a way that meets your high expectations. ### Find the best luxury hotels and resorts in Winter Park For those seeking an opulent escape in Winter Park, Florida, these luxurious hotels promise an unforgettable experience, blending elegance with top amenities. [The Alfond Inn](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information) - **Why it's great for a luxury retreat:** The Alfond Inn stands as a beacon of luxury in Winter Park, an impressive guest review rating of 9.4. This boutique hotel features premium bedding and designer toiletries, ensuring that guests enjoy the utmost comfort during their stay. With its outstanding concierge services and inviting poolside bar, The Alfond Inn makes for a perfect retreat for discerning travellers seeking relaxation and sophistication. - **Other amenities:** Guests can indulge in a range of wellness treatments at the onsite spa, including Swedish massages and body scrubs, while the outdoor pool offers a serene escape with sun loungers and umbrellas. The hotel also provides valet parking for added convenience, as well as spacious suites with separate living areas for an elevated stay. A beautiful terrace and lush garden enhance the luxurious feel, making it a perfect choice for those looking to unwind in style. - **Nearby attractions:** Casa Feliz Historic Home Museum - 1.1 km, Orlando Museum of Art - 3.8 km ## Top Winter Park Hotel Reviews ![Marriott's Grande Vista](//images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "Loved the resort. Very easy to navigate and staff was extra friendly and helpful. Me and my family will definitely come back " [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.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 "Good" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Hyatt Regency Orlando](//images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "Layout of the hotel." [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) ![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 "Staff Resa was very courteous" [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Avanti International Resort](//images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967_y.jpg) ### Avanti International Resort 10/10 Excellent "It was very nice here, alot to do around the area that's in walking distance. The elevators were so hot and staying in building 3 facing the highway forget about sleep if your a light sleeper you can hear the traffic all day and night. " [](https://expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.Hotel-Information) ![Rosen Inn at Pointe Orlando](//images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "Wow! This property really blew us out of the water with how great it was for the price. We will be staying again, and highly recommend for anyone travelling to Universal and/or Disney!" [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Universal's Cabana Bay Beach Resort](//images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "It was good " [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.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 " Very family friendly, welcoming, and relaxing " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Hyatt Regency Orlando International Airport](//images.trvl-media.com/lodging/1000000/10000/2800/2754/acaa1e8b_y.jpg) ### Hyatt Regency Orlando International Airport 10/10 Excellent "Parking was easier today. Check in was easy and the boarding process was simple. " [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando-International-Airport.h2754.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to Winter Park? > During your visit, you might want to enjoy the university which Winter Park is known for. ### What's the best high-end hotel in Winter Park? > [The Alfond Inn](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information) is a luxury hotel with spa services and valet parking, and it's a popular choice for Expedia travelers looking for an elegant place to stay. ### When can I expect good weather in Winter Park? > Planning for the weather is an important factor for making your trip to Winter Park a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Park are August, September, July, and June, with each month seeing an average of 7 inches of rainfall. ### What's there to see and do in Winter Park? > When you're in Winter Park, enjoy exploring the sights and attractions here including Casa Feliz Historic Home Museum, Winter Park Village, and Albin Polasek Museum and Sculpture Gardens. If you have some spare time during your trip, you might want to check out Winter Park Country Club and Morse Museum of American Art. ### How can I get around Winter Park? > It's easier to get around town comfortably when you know your options. 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