Title: Winter Park Vacation Rentals from $93: Search Short-Term Rentals | Expedia.com [Winter Park Travel Guide](https://expedia.com/Winter-Park.dx7902)[Hotels in Winter Park](https://expedia.com/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Flights to Winter Park](https://expedia.com/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Things to do in Winter Park](https://expedia.com/Things-To-Do-In-Winter-Park.d7902.Travel-Guide-Activities)[Car Rentals in Winter Park](https://expedia.com/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.com/Winter-Park.d7902.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=APART_HOTEL) Villas [](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=VILLA) Condos [](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CONDO) Cottages [](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=COTTAGE) Apartments [](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=APARTMENT) Cabins [](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CABIN) Chalets [](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CHALET) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=HOUSE_BOAT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals) ## Top Winter Park Hotel Reviews ![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/cae40483_y.jpg) ### DoubleTree by Hilton at the Entrance to Universal Orlando 10/10 Excellent "Staff was great!" [](https://expedia.com/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/4c48bd3d_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "Everyone had a great time - the staff was very helpful and nice. " [](https://expedia.com/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/91c45539_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 8/10 Good "Rooms were nice size, big pools, multiple pools, activity centers closed kind of early but there is a lot of features like shuffleboard, basketball, volleyball, and putt putt to do on site. We heard the restaurants weren't the greatest so we didn't eat there, but that may just be a poor reference. The room had some random weird stains (pet? But there were no pets allowed) but for the most part was a pleasant place to stay. Bathrooms were nice. Even pool bathrooms were nice. Plan to stay again when we travel to Orlando." [](https://expedia.com/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Drury Plaza Hotel Orlando - Disney Springs Area](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/6af5b762_y.jpg) ### Drury Plaza Hotel Orlando - Disney Springs Area 10/10 Excellent "The room was clean, and despite the high volume of guests, the lobby area was consistently well maintained. Breakfast was enjoyable and offered a good start to the day. While the mattresses are somewhat worn, it did not impact the overall quality of my stay. I would gladly stay here again." [](https://expedia.com/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.Hotel-Information) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 8/10 Good "AC wasn't working the first night. Was taken care of fairly promptly. " [](https://expedia.com/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 8/10 Good "The pool areas were nice but over crowded. The food was good not great Nice young man named christian stopped us on our way out, just super friendly and gave us a ride with our luggage. The nicest employee, I encountered there although most of the staff was friendly. " [](https://expedia.com/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![Caribe Royale Orlando](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/075cd42b_y.jpg) ### Caribe Royale Orlando 10/10 Excellent "Good Orlando hotel. Value hotel." [](https://expedia.com/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) ![Fairfield Inn & Suites Lake Buena Vista in Marriott Village](https://images.trvl-media.com/lodging/1000000/480000/470900/470892/w4000h2663x0y0-13fc5e39_y.jpg) ### Fairfield Inn & Suites Lake Buena Vista in Marriott Village 6/10 Okay "Clean room - however very minimal amenities. Same breakfast every day. " [](https://expedia.com/Orlando-Hotels-Fairfield-Inn-Suites-Lake-Buena-Vista-In-Marriott-Village.h470892.Hotel-Information) ![B&B Hotel Orlando International Drive Near Universal - Newly Renovated!](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/ca31fce1_y.jpg) ### B&B Hotel Orlando International Drive Near Universal - Newly Renovated! 10/10 Excellent "Our room was visibly updated and very clean. Perfect for myself and 2 teenage boys. The shower was unique with 2 different shower heads and great pressure. Beds were comfortable. Thermostat worked great. The location was perfect for visiting parks, specifically Universal for us. We had walking access to local restaurants and stores but also public transportation to other places. Would definitely stay again." [](https://expedia.com/Orlando-Hotels-Floridian-Express-Extended-Stay-Hotel.h26703.Hotel-Information) ## Find out more about Winter Park **Everything you need to know about Winter Park vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Winter Park vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Winter Park. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Park in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $93 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Winter Park rentals** At Expedia, we put the best Winter Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Winter Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Park vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Recommended Vacation Rental Destinations - Trending destinations on Expedia.com - All accommodation types in Winter Park - [Orlando Vacation Rentals ](https://expedia.com/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals) - [Space Coast Vacation Rentals ](https://expedia.com/Space-Coast-Vacation-Rentals.d6047880.Travel-Guide-VacationRentals) - [Tampa Vacation Rentals ](https://expedia.com/Tampa-Vacation-Rentals.d602996.Travel-Guide-VacationRentals) - [St. Augustine Vacation Rentals ](https://expedia.com/St-Augustine-Vacation-Rentals.d6047864.Travel-Guide-VacationRentals) - [Savannah Vacation Rentals ](https://expedia.com/Savannah-Vacation-Rentals.d6034190.Travel-Guide-VacationRentals) - [Sumter Vacation Rentals ](https://expedia.com/Sumter-Vacation-Rentals.d6058099.Travel-Guide-VacationRentals) - 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[Aparthotels in Winter Park ](https://expedia.com/Winter-Park-Apart-Hotels.d7902-aaApartHotels.Travel-Guide-Accommodation) - [Town Houses in Winter Park ](https://expedia.com/Winter-Park-Town-Houses.d7902-aaTownHouses.Travel-Guide-Accommodation) - [Guest Houses in Winter Park ](https://expedia.com/Winter-Park-Guest-Houses.d7902-aaGuestHouses.Travel-Guide-Accommodation) - [Condo Resorts in Winter Park ](https://expedia.com/Winter-Park-Condominium-Resort.d7902-aaCondominiumResort.Travel-Guide-Accommodation) - [B&B in Winter Park ](https://expedia.com/Winter-Park-Bed-And-Breakfast.d7902-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Winter Park ](https://expedia.com/Winter-Park-Motels.d7902-aaMotels.Travel-Guide-Accommodation) - [Chalets in Winter Park ](https://expedia.com/Winter-Park-Chalets.d7902-aaChalets.Travel-Guide-Accommodation) - [Houseboats in Winter Park ](https://expedia.com/Winter-Park-Houseboats.d7902-aaHouseboats.Travel-Guide-Accommodation) - [Farmstay in Winter Park ](https://expedia.com/Winter-Park-Agritourism.d7902-aaAgritourism.Travel-Guide-Accommodation) - 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