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Over 10,000 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 4.92 out of 538 reviews
Cozy Apartment With Resort Style Amenities!
4 guests · 2 bedrooms · 2 beds · 2 baths
Pool · Wifi · Kitchen · Air conditioning
Price:$68 / night
SUPERHOST
Entire guesthouse
Rating 4.96 out of 5197 reviews
The Shed in Downtown Orlando
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Kitchen · Air conditioning
Price:$73 / night
SUPERHOST
Entire guest suite
Rating 4.98 out of 542 reviews
East End Escape
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Air conditioning
Price:$69 / night
SUPERHOST
Entire guest suite
Rating 4.96 out of 5162 reviews
Atmospheric Studio in the Garden
3 guests · Studio · 1 bed · 1 bath
Wifi · Kitchen · Air conditioning
Price:$68 / night
Entire guesthouse
Rating 4.66 out of 5143 reviews
Winter Park Private Quaint Guest House
2 guests · Studio · 1 bed · 1 bath
Wifi · Air conditioning
Price:$62 / night
SUPERHOST
Entire condominium
Rating 4.91 out of 5101 reviews
Apt E -Cozy Comfort in the Heart of Winter Park
4 guests · 2 bedrooms · 2 beds · 1 bath
Pool · Wifi · Kitchen · Air conditioning
Price:$81 / night
SUPERHOST
Entire guesthouse
Rating 4.87 out of 5275 reviews
Chez Bienvenu
3 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Kitchen · Air conditioning
Price:$67 / night
SUPERHOST
Entire guesthouse
Rating 4.92 out of 550 reviews
Cozy Winter Park Guesthouse
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Kitchen · Air conditioning
Price:$75 / night
SUPERHOST
Entire guest suite
Rating 4.94 out of 5122 reviews
Winter Park Charm (Close proximity to Park Ave)
4 guests · 2 bedrooms · 3 beds · 1 bath
Wifi · Air conditioning
Price:$110 / night
SUPERHOST
Entire townhouse
Rating 4.89 out of 5117 reviews
Entire Cozy Beautiful 3 Bedroom Orlando Townhouse
6 guests · 3 bedrooms · 3 beds · 1.5 baths
Pool · Wifi · Kitchen · Air conditioning
Price:$90 / night
SUPERHOST
Entire guesthouse
Rating 4.84 out of 5141 reviews
#8 WELCOME HOME IN WINTER PARK
2 guests · Studio · 1 bed · 1 bath
Wifi · Kitchen · Air conditioning
Price:$88 / night
SUPERHOST
Entire guest suite
Rating 4.93 out of 528 reviews
Balfour Palms
2 guests · Studio · 1 bed · 1 bath
Wifi · Kitchen · Air conditioning
Price:$75 / night
SUPERHOST
Entire house
Rating 4.96 out of 527 reviews
Mediterranean abode on a historic Golf Course.
4 guests · 2 bedrooms · 4 beds · 1 bath
Wifi · Kitchen · Air conditioning
Price:$85 / night
SUPERHOST
Entire apartment
Rating 4.96 out of 579 reviews
College Park Mid-Century Duplex
4 guests · 2 bedrooms · 2 beds · 1 bath
Wifi · Kitchen · Air conditioning
Price:$65 / 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 · Air conditioning
Price:$69 / night
Entire house
Rating 4.85 out of 513 reviews
WeLive Winter Park / Spacious Enclave W/ Patio!
10 guests · 4 bedrooms · 5 beds · 1 bath
Wifi · Kitchen · Air conditioning
Price:$67 / night
SUPERHOST
Entire guest suite
Rating 4.98 out of 559 reviews
Winter Park Suite with Private Entrance & Kitchen
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Kitchen · Air conditioning
Price:$75 / night
SUPERHOST
Entire condominium
Rating 4.95 out of 581 reviews
Apt H -Walkabout in the Heart of Winter Park
4 guests · 2 bedrooms · 2 beds · 1 bath
Pool · Wifi · Kitchen · Air conditioning
Price:$73 / night
1 18 of 300+ Rentals
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