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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 apartment
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
Price:$68 / night
Entire guesthouse
Rating 4.67 out of 5155 reviews
Winter Park Private Quaint Guest House
2 guests · Studio · 1 bed · 1 bath
Wifi · Free parking
Price:$62 / night
Entire guest suite
Rating 4.74 out of 550 reviews
Private Access Entire Garden Suite in College Park
3 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Free parking · Kitchen
Price:$40 / night
SUPERHOST
Entire guesthouse
Rating 4.92 out of 553 reviews
Cozy Winter Park Guesthouse
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Free parking · Kitchen
Price:$75 / night
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
Price:$68 / night
SUPERHOST
Entire guesthouse
Rating 4.87 out of 5276 reviews
Chez Bienvenu
3 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Free parking · Kitchen
Price:$67 / night
SUPERHOST
Entire guest suite
Rating 4.98 out of 555 reviews
East End Escape
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Free parking
Price:$78 / night
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
Price:$92 / night
SUPERHOST
Entire apartment
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
Price:$69 / night
SUPERHOST
Private room
Rating 4.92 out of 565 reviews
Downtown Orlando - Private Room
2 guests · 1 bedroom · 1 bed · 1 private bath
Wifi · Free parking · Kitchen
Price:$39 / night
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
Price:$69 / night
Private room
Rating 4.75 out of 552 reviews
Quarto # 3 para alugar em Winter Park
2 guests · 1 bedroom · 2 beds · 1 shared bath
Wifi · Free parking · Kitchen
Price:$30 / night
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
Price:$110 / night
SUPERHOST
Private room
Rating 4.77 out of 582 reviews
Modern Oasis by Park Avenue/ Rollins/Full Sail RM1
2 guests · 1 bedroom · 1 bed · 1 shared bath
Pool · Wifi · Free parking · Kitchen
Price:$49 / night
SUPERHOST
Entire house
Rating 4.85 out of 539 reviews
Mediterranean abode on a historic Golf Course.
4 guests · 2 bedrooms · 4 beds · 1 bath
Wifi · Free parking · Kitchen
Price:$85 / night
Entire apartment
Rating 4.92 out of 525 reviews
Winter Park Bamboo Loft
4 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Free parking · Kitchen
Price:$61 / night
SUPERHOST
Entire guest suite
Rating 4.91 out of 532 reviews
Balfour Palms
2 guests · Studio · 1 bed · 1 bath
Wifi · Free parking · Kitchen
Price:$75 / night
SUPERHOST
Entire guest suite
Rating 4.86 out of 535 reviews
QUAINT UPDATED STUDIO IN WINTER PARK, FL
2 guests · Studio · 1 bed · 1 bath
Wifi · Free parking
Price:$50 / night
1 18 of 300+ Rentals
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