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 ![](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 Winter Park Luxury Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-14&endDate=2025-10-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-15&endDate=2025-10-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-24&endDate=2025-10-26&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) ![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) ![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) ![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 $416 CA $507 total includes taxes & fees Oct 26 - Oct 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) ![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) ![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) ### Park Plaza Hotel Park Avenue District 8.6/10 Excellent (1007) "Excellent location, beautiful 100-year-old hotel " CA $207 CA $233 total includes taxes & fees Oct 16 - Oct 17 [](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=2025-10-28&endDate=2025-10-29®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 "Very clean room. Accommodating staff and beautiful property with a lot of food and entertainment " [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.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 "Very convenient property in Orlando airport terminal. Nice clean rooms comfortable beds. Great views of planes. " [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando-International-Airport.h2754.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 "Everything was perfect " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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 "Very friendly staff and budget friendly hotel with great water park and restaurants close by." [](https://expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.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 "My weekend stay was awesome, my wife and I loved the hotel the moment we entered the staff was very helpful and pleasant. We had slight challenge in our room and it was corrected in a timely manner. We will definitely be back!!" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](//images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Plenty of swimming areas for kids and volleyball area. I especially loved the calming lake view from our balcony." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Ramada by Wyndham Suites Orlando Airport](//images.trvl-media.com/lodging/1000000/130000/120400/120303/2eaf4a61_y.jpg) ### Ramada by Wyndham Suites Orlando Airport 10/10 Excellent "The halls smell HORRIBLE! the carpets stink. The are old " [](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Suites-Orlando-Airport.h120303.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 nice I saw kids enjoying the lazy river on one pool and the slide had kids playing with no problem. I have 7 kids and I think they would really enjoy this resort." [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.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 is always friendly and rooms are always clean! My go to hotel for an off property Disney trip! " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.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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