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Enter dates and number of guests to see the total price per night.
Over 9,000 guest reviews for places to stay in Winter Park, with an average of 4.9 out of 5 stars.

300+ places to stay

SUPERHOST
Entire flat
Rating 4.83 out of 543 reviews
Cozy Apartment With Resort Style Amenities!
4 guests · 2 bedrooms · 2 beds · 2 baths
Pool · Wifi · Free parking · Kitchen
Entire guesthouse
Rating 4.68 out of 5152 reviews
Winter Park Private Quaint Guest House
2 guests · Studio · 1 bed · 1 bath
Wifi · Free parking
SUPERHOST
Entire guesthouse
Rating 4.96 out of 5210 reviews
The Shed in Downtown Orlando
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Kitchen
SUPERHOST
Entire guest suite
Rating 4.95 out of 5168 reviews
Atmospheric Studio in the Garden
3 guests · Studio · 1 bed · 1 bath
Wifi · Free parking · Kitchen
SUPERHOST
Entire guest suite
Rating 4.98 out of 553 reviews
East End Escape
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Free parking
SUPERHOST
Entire condominium
Rating 4.91 out of 5106 reviews
Apt E -Cozy Comfort in the Heart of Winter Park
4 guests · 2 bedrooms · 2 beds · 1 bath
Pool · Wifi · Free parking · Kitchen
SUPERHOST
Entire guesthouse
Rating 4.92 out of 552 reviews
Cozy Winter Park Guesthouse
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Free parking · Kitchen
SUPERHOST
Entire guesthouse
Rating 4.87 out of 5276 reviews
Chez Bienvenu
3 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Free parking · Kitchen
SUPERHOST
Entire guesthouse
Rating 4.84 out of 5143 reviews
#8 WELCOME HOME IN WINTER PARK
2 guests · Studio · 1 bed · 1 bath
Wifi · Free parking · Kitchen
SUPERHOST
Entire townhouse
Rating 4.88 out of 5122 reviews
Entire Cozy Beautiful 3 Bedroom Orlando Townhouse
6 guests · 3 bedrooms · 3 beds · 1.5 baths
Pool · Wifi · Free parking · Kitchen
Entire house
Rating 4.44 out of 518 reviews
Luxury Pool smart-home
8 guests · 3 bedrooms · 3 beds · 2 baths
Pool · Wifi · Free parking · Kitchen
SUPERHOST
Entire guest suite
Rating 4.94 out of 5124 reviews
Winter Park Charm (Close proximity to Park Ave)
4 guests · 2 bedrooms · 3 beds · 1 bath
Wifi
SUPERHOST
Entire guest suite
Rating 4.90 out of 531 reviews
Balfour Palms
2 guests · Studio · 1 bed · 1 bath
Wifi · Free parking · Kitchen
SUPERHOST
Entire house
Rating 4.86 out of 537 reviews
Mediterranean abode on a historic Golf Course.
4 guests · 2 bedrooms · 4 beds · 1 bath
Wifi · Free parking · Kitchen
Entire flat
Rating 4.91 out of 523 reviews
Winter Park Bamboo Loft
4 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Free parking · Kitchen
SUPERHOST
Entire condominium
Rating 4.97 out of 5117 reviews
Just 3 Blocks to Shops/Restaurants on Park Ave!
6 guests · 3 bedrooms · 4 beds · 2.5 baths
Pool · Wifi · Free parking · Kitchen
SUPERHOST
Entire condominium
Rating 4.95 out of 587 reviews
Apt H -Walkabout in the Heart of Winter Park
4 guests · 2 bedrooms · 2 beds · 1 bath
Pool · Wifi · Free parking · Kitchen
SUPERHOST
Entire guesthouse
Rating 4.93 out of 5291 reviews
Charming Guest House in Winter Park
3 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Free parking
118 of 300+ Rentals
Enter dates to see full pricing. Additional fees apply. Taxes may be added. Free cancellation only applicable within 48 hours from booking.