Title: Winter Park Guest Houses from CA $213 | 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/res70/338000/338515-Lake-Virginia-Winter-Park.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses in Winter Park from CA $213 ![](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 prices for these dates Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winter Park Guest Houses ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/4a5ba30d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/1f721d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/3a229cea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/eb10fab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mills Cottage by the Little Lake Lake Weldona 10/10 Exceptional (49) "Super charming " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lucas CA $201 CA $483 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orlando-Hotels-Mills-Cottage-On-Small-Lake.h35738680.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/24000000/23710000/23708700/23708648/88091df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/24000000/23710000/23708700/23708648/aff7b581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/24000000/23710000/23708700/23708648/84f97ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/24000000/23710000/23708700/23708648/w1440h945x0y6-0571883c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Lake Eola Historic House 1 OR 2 BED Downtown Orlando 8.8/10 Excellent (31) "Good stay everything that we wanted was in walking distance and it was comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas E. CA $95 CA $213 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Orlando-Hotels-1-2-Bedroom-Cottage-Apartment-Across-From-Lake-Eola-Downtown.h23708648.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/88000000/87810000/87802200/87802118/69b416fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87810000/87802200/87802118/a753674b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/88000000/87810000/87802200/87802118/04807f02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/88000000/87810000/87802200/87802118/e316b85a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic lakefront guesthouse Orlando 10/10 Exceptional (8) "Had ana amazing time! The owner is very responsive and the place was a total vibe " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan O. CA $133 CA $395 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Villa-With-Lake-Views.h87802118.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/95000000/94910000/94902800/94902727/w905h683x59y0-81b7810c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94910000/94902800/94902727/w507h683x260y0-f7900d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/95000000/94910000/94902800/94902727/399556b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/95000000/94910000/94902800/94902727/w528h683x248y0-4a684230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 1BR apt-Pool/Tennis/Gym/Near attractions Buena Ventura Lakes CA $114 CA $296 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Orlando-Hotels-Cozy-1BR-Apt-PoolTennisGymNear-Attractions.h94902727.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=2025-11-05&endDate=2025-11-06®ionId=7902&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Guest-Houses.d7902-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Guest-Houses.d7902-aaGuestHouses.Travel-Guide-Accommodation) ## 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 "Todo perfecto me encanto" [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.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 nice place for families. " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.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 "As much as I would have loved to have had breakfast.I did not because the child in the next room which the doors were like.Paper woke me up at five a m. The coffee maker didn't work in my room. And therefore, I didn't have time for breakfast. I was too irritated at that point. The room was very clean and wonderful.Had it not been for the paper thin walls and the child waking me up.I would have had a nice quiet evening" [](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Suites-Orlando-Airport.h120303.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](//images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 10/10 Excellent "Very clean room and the balcony I could see the lake it was such a beautiful site especially in the early mornings. " [](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![DoubleTree by Hilton Orlando Airport](//images.trvl-media.com/lodging/1000000/20000/12300/12270/5d85f82f_y.jpg) ### DoubleTree by Hilton Orlando Airport 10/10 Excellent "The staff were amazing! " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Orlando-Airport.h12270.Hotel-Information) ![Universal's Endless Summer Resort - Dockside Inn and Suites](//images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/c8859517_y.jpg) ### Universal's Endless Summer Resort - Dockside Inn and Suites 10/10 Excellent "El cuarto lo limpiaban, pero es algo como por encima para salir del paso." [](https://expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.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 "I had a beautiful view volcano bay from my hotel room and there was beautiful pool with a little restaurant by the pool" [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.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 "Room very clean and all staff we encountered were very helpful and pleasant." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Avanti International Resort](//images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967_y.jpg) ### Avanti International Resort 10/10 Excellent "The theme park shuttle was extremely helpful!! " [](https://expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.Hotel-Information) ## Find out more about Winter Park ## Winter Park Guest Houses information | Number of reviews | 84 | | --- | --- | | Accommodation | 28 Guest Houses | | Lowest Price | CA $213 | | Highest Price | CA $483 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hyatt Hotels in Aloma](https://www.expedia.ca/Aloma-Orlando-Hotels-Hyatt-Hotels.0-n553248635975863638-0--bHyattHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Aloma](https://www.expedia.ca/Aloma-Orlando-Hotels-Spa-Hotel.0-n553248635975863638-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Aloma Hotels](https://www.expedia.ca/Aloma-Orlando-Hotels.0-n553248635975863638-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Altamonte Springs](https://www.expedia.ca/Altamonte-Springs-Apart-Hotels.d5965-aaApartHotels.Travel-Guide-Accommodation) - [Guest Houses in Altamonte Springs](https://www.expedia.ca/Altamonte-Springs-Guest-Houses.d5965-aaGuestHouses.Travel-Guide-Accommodation) - [Resorts in Altamonte Springs](https://www.expedia.ca/Altamonte-Springs-Resort-Hotels.d5965-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Altamonte Springs](https://www.expedia.ca/Altamonte-Springs-Townhomes.d5965-aaTownhomes.Travel-Guide-Accommodation) - [Inns in Cape Canaveral](https://www.expedia.ca/Cape-Canaveral-Inns.d6484-aaInns.Travel-Guide-Accommodation) - [Lodges in Cape Canaveral](https://www.expedia.ca/Cape-Canaveral-Lodges.d6484-aaLodges.Travel-Guide-Accommodation) - [Ranches in Cape Canaveral](https://www.expedia.ca/Cape-Canaveral-Ranches.d6484-aaRanches.Travel-Guide-Accommodation) - [Hotels near Casa Feliz Historic Home Museum](https://www.expedia.ca/Casa-Feliz-Historic-Home-Museum-Hotels.0-l6154784-0.Travel-Guide-Filter-Hotels) - [Hotels near Crealde School of Art](https://www.expedia.ca/Crealde-School-Of-Art-Hotels.0-l6239848-0.Travel-Guide-Filter-Hotels) - [Motels in Eatonville](https://www.expedia.ca/Eatonville-Motels.d12161-aaMotels.Travel-Guide-Accommodation) - [Aparthotels in Fern Park](https://www.expedia.ca/Fern-Park-Apart-Hotels.d7377-aaApartHotels.Travel-Guide-Accommodation) - [Holiday Park Resorts in Fern Park](https://www.expedia.ca/Fern-Park-Holiday-Parks.d7377-aaHolidayParks.Travel-Guide-Accommodation) - [Houseboats in Fern Park](https://www.expedia.ca/Fern-Park-Houseboats.d7377-aaHouseboats.Travel-Guide-Accommodation) - [Inns in Fern Park](https://www.expedia.ca/Fern-Park-Inns.d7377-aaInns.Travel-Guide-Accommodation) - [Resorts in Fern Park](https://www.expedia.ca/Fern-Park-Resort-Hotels.d7377-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Fern Park](https://www.expedia.ca/Fern-Park-Townhomes.d7377-aaTownhomes.Travel-Guide-Accommodation) - [Pensions in Florida](https://www.expedia.ca/Florida-Pensions.d211-aaPensions.Travel-Guide-Accommodation) - [Pousadas in Florida](https://www.expedia.ca/Florida-Pousadas.d211-aaPousadas.Travel-Guide-Accommodation) - [Hotels near Full Sail University](https://www.expedia.ca/Full-Sail-University-Hotels.0-l6154770-0.Travel-Guide-Filter-Hotels) - [Hotels near Harry P. 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Leu Gardens](https://www.expedia.ca/Harry-P-Leu-Gardens-Orlando.d6068689.Vacation-Attraction) - [Kraft Azalea Gardens](https://www.expedia.ca/Kraft-Azalea-Gardens-Orlando.d553248621532654339.Vacation-Attraction) - [Lake Virginia](https://www.expedia.ca/Lake-Virginia-Orlando.d553248621532654331.Vacation-Attraction) - [Mead Garden](https://www.expedia.ca/Mead-Garden-Orlando.d6239861.Vacation-Attraction) - [Visit Aloma](https://www.expedia.ca/Orlando-Aloma.dx553248635975863638) - [Visit Orwin Manor](https://www.expedia.ca/Orlando-Orwin-Manor.dx553248635976471367) - [Orlando Vacations](https://www.expedia.ca/Orlando.d178294.Destination-Travel-Guides) - [Rollins Museum of Art](https://www.expedia.ca/Rollins-Museum-Of-Art-Orlando.d6154782.Vacation-Attraction) - [Village Plaza Shopping Center](https://www.expedia.ca/Village-Plaza-Shopping-Center-Orlando.d553248621558036314.Vacation-Attraction) - [Walt Disney World® Resort](https://www.expedia.ca/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction) - [Winter Pines Golf Club](https://www.expedia.ca/Winter-Pines-Golf-Club-Orlando.d6239892.Vacation-Attraction) - [Car rental Maitland](https://www.expedia.ca/Car-Rentals-In-Maitland.d8442.Car-Rental-Guide) - [Rental cars Orlando Intl. airport](https://www.expedia.ca/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide) - [Car rentals near Orlando](https://www.expedia.ca/Car-Rentals-In-Orlando.d178294.Car-Rental-Guide) - [Maitland Vacation Rentals](https://www.expedia.ca/Maitland-Vacation-Rentals.d8442.Travel-Guide-VacationRentals) - [Orlando Vacation Rentals](https://www.expedia.ca/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals) - [Things to do in Orlando](https://www.expedia.ca/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities) - [Book Guest Houses in Winter Park on Expedia.com](https://www.expedia.com/Winter-Park-Guest-Houses.d7902-aaGuestHouses.Travel-Guide-Accommodation)