Search Guest Houses in Winter Park from CA $167
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for Winter Park guest houses
1. Downtown Lake Eola Historic House 1 OR 2 BED
Downtown Lake Eola Historic House 1 OR 2 BEDDowntown Orlando
9.4 out of 10, Exceptional, (53 reviews)
"We loved our stay, conveniently close to all the downtown Orlando restaurants, and bars, we enjoyed walking around, definitely recommend it."
Cristina T.
The price is CA $104
CA $232 total
includes taxes & fees
Oct 12 - Oct 13
2. Mills Cottage by the Little Lake
Mills Cottage by the Little LakeLake Weldona
9.6 out of 10, Exceptional, (68 reviews)
"Great stay. "
rick s.
The price is CA $278
CA $588 total
includes taxes & fees
Oct 14 - Oct 15
3. Quiet Oasis in Lovely Neighborhood
Quiet Oasis in Lovely NeighborhoodSouthern Oaks
9.8 out of 10, Exceptional, (199 reviews)
"The room was clean. It was close to a lot of the activities we wanted to do. The best part was getting to meet and engage with the owners who are wonderful people."
Andy K.
The price is CA $115
CA $270 total
includes taxes & fees
Oct 14 - Oct 15
4. Historic lakefront guesthouse
Historic lakefront guesthouseOrlando
10.0 out of 10, Exceptional, (15 reviews)
"Nice place, really roomy—perfect for decompressing after a busy week of training. The pool, hot tub, and lake were beautiful, and the location is close to everything.Jason was a great host—easy to communicate with and everything was smooth from start to finish.Easy stay, no stress. Would definitely come back."
STEVE O.
The price is CA $141
CA $446 total
includes taxes & fees
Oct 13 - Oct 14
5. New King GH|PetsOK|PrivEnt|Pvt FncdYard+Tub+W/D+FP
New King GH|PetsOK|PrivEnt|Pvt FncdYard+Tub+W/D+FPOrlando
10.0 out of 10, Exceptional, (1 review)
"Great communication!"
Crystal M.
The price is CA $110
CA $242 total
includes taxes & fees
Nov 2 - Nov 3
The price is CA $61
CA $167 total
includes taxes & fees
Oct 27 - Oct 28
7. Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Cozy 1BR apt-Pool/Tennis/Gym/Near attractionsBuena Ventura Lakes
The price is CA $115
CA $303 total
includes taxes & fees
Oct 16 - Oct 17
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.
Top Winter Park Hotel Reviews
Hyatt Regency Orlando International Airport
10/10 Excellent
Find out more about Winter Park
Winter Park Guest Houses information
Number of reviews | 334 |
|---|---|
Accommodation | 32 Guest Houses |
Lowest Price | CA $167 |
Highest Price | CA $588 |
Explore a world of travel with Expedia
- Condo Resorts in Orlando
- Walt Disney World Resort in Orlando
- Kissimmee Hotels
- Condo Rentals in Orlando
- Motels in Fern Park
- B&B in Orlando
- Lodges in Orlando
- Universal Orlando Resort in Orlando
- Apartments in Orlando
- Waterpark Hotels in Orlando
- Houseboats in Fern Park
- Vacation Homes in Orlando
- Condo Rentals in Winter Park
- 777bd
- Adults Only Resorts & in Orlando
- Resorts in Orlando
- Orlando Hotels
- Villas in Orlando
- Guest Houses in Orlando
- Hotels near Universal Studios Florida
- Resorts in North Orlando
- Hotels with a Lazy River in Orlando
- Hostels in Casselberry
- Aparthotels in Orlando
- All Inclusive Resorts and in Florida
- Cruise Ships in Orlando
- Guest Houses in Altamonte Springs
- Cabin Rentals in Northeast Orlando
- Hotels near Walt Disney World® Resort
- Motels in Orlando
- Family Hotels in Orlando
- Drury Plaza Hotel Orlando
- Cottages in Orlando
- 5 Star Hotels in Orlando
- All Inclusive Resorts and in Orlando
- B&B in Longwood
- Hotels near Orlando Intl.
- Hotels with Free Airport Shuttle in Orlando
- Guest Houses in Fern Park
- Townhomes in Orlando
- Rv Parks in Orlando
- B&B in Maitland
- Hostels in Orlando
- Hotels near Orange County Convention Center
- Cabin Rentals in Orlando
- Houseboats in Orlando
- Hilton Vacation Club Mystic Dunes Orlando
- Cabin Rentals in Maitland
- Farmstay in Orlando
- Cheap Hotels in Orlando
- Flights from Ogdensburg (OGS) to Orlando (MCO)
- Flights from Bangor (BGR) to Orlando (MCO)
- Flights from Windsor (YQG) to Orlando (MCO)
- Flights from Miami (MIA) to Orlando (MCO)
- Flights from Ottawa (YOW) to Orlando (MCO)
- Flights from Toronto (YYZ) to Orlando (ORL)
- Flights to Florida
- Flights from Hamilton (YHM) to Orlando (MCO)
- Flights from Kitchener (YKF) to Orlando (MCO)
- Flights from Montreal (YUL) to Orlando (MCO)
- Flights from New York (JFK) to Orlando (MCO)
- Flights from Moncton (YQM) to Orlando (MCO)
- Flights from Orlando Intl.
- Flights from Vancouver (YVR) to Orlando (MCO)
- Flights to Orlando
- Flights from Buffalo (BUF) to Orlando (MCO)
- Flights from St. John's (YYT) to Orlando (MCO)
- Flights from Edmonton (YEG) to Orlando (MCO)
- Flights from Plattsburgh (PBG) to Orlando (MCO)
- Flights from Detroit (DTW) to Orlando (MCO)
- Flights from Regina (YQR) to Orlando (MCO)
- Flights from Halifax (YHZ) to Orlando (MCO)
- Flights from London (YXU) to Orlando (MCO)
- Flights from Syracuse (SYR) to Orlando (MCO)
- Flights from Fort Lauderdale (FLL) to Orlando (MCO)
- Flights from Winnipeg (YWG) to Orlando (MCO)
- Flights from Seattle (SEA) to Orlando (MCO)
- Flights from Calgary (YYC) to Orlando (MCO)
- Flights from Saskatoon (YXE) to Orlando (MCO)
- Flights from Toronto (YYZ) to Orlando (MCO)
- Flights from Orlando Sanford Intl.
- Florida Vacations
- Universal Studios Florida
- Walt Disney World® Resort
- The Wizarding World of Harry PotterTM
- Universal Orlando Resort
- All inclusive Vacation Packages Florida
- Orlando Vacations
- Universal’s Volcano Bay
- All inclusive Vacation Packages Orlando
- Disney's Hollywood Studios®
- Orlando International Premium Outlets