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300+ stays

Stays in Winter Park

Over 9,000 guest reviews for places to stay in Winter Park, with an average of 4.9 out of 5 stars.
SUPERHOST
Entire guesthouse
The Shed in Downtown Orlando
2 guests1 bedroom1 bed1 bath
WifiAir conditioning
Includes cancellation flexibility
Price:$39 / night
SUPERHOST
Entire house
2 min to DownTown Orlando/20-30 min to Disney park
4 guests2 bedrooms2 beds1 bath
WifiFree parkingAir conditioning
Price:$68 / night
Entire apartment
Cozy Apartment With Resort Style Amenities!
4 guests2 bedrooms2 beds2 baths
PoolWifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$68 / night
SUPERHOST
Entire guest suite
East End Escape
2 guests1 bedroom1 bed1 bath
WifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$69 / night
SUPERHOST
Entire guest suite
The Master @ Oasis in Orlando
2 guests1 bedroom1 bed1 bath
WifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$49 / night
Entire guesthouse
Winter Park Private Quaint Guest House
2 guestsStudio1 bed1 bath
WifiFree parkingAir conditioning
Price:$62 / night
SUPERHOST
Entire guest suite
Atmospheric Studio in the Garden
3 guestsStudio1 bed1 bath
WifiFree parkingAir conditioning
Price:$76 / night
SUPERHOST
Entire guest suite
QUAINT UPDATED STUDIO IN WINTER PARK, FL
2 guestsStudio1 bed1 bath
WifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$30 / night
SUPERHOST
Entire guesthouse
Cozy Winter Park Guesthouse
2 guests1 bedroom1 bed1 bath
WifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$75 / night
SUPERHOST
Entire apartment
Apt C -Modern Elegance in the Heart of Winter Park
4 guests2 bedrooms2 beds2 baths
PoolWifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$62 / night
Entire house
WeLive Winter Park / Spacious Enclave W/ Patio!
10 guests4 bedrooms5 beds1 bath
WifiFree parkingAir conditioning
Price:$55 / night
SUPERHOST
Entire townhouse
Entire Cozy Beautiful 3 Bedroom Orlando Townhouse
6 guests3 bedrooms3 beds1.5 baths
PoolWifiFree parkingAir conditioning
Price:$90 / night
SUPERHOST
Entire guest suite
Winter Park Charm (Close proximity to Park Ave)
4 guests2 bedrooms3 beds1 bath
WifiAir conditioning
Includes cancellation flexibility
Price:$110 / night
Entire apartment
Winter Park Bamboo Loft
4 guests1 bedroom1 bed1 bath
WifiFree parkingAir conditioning
Price:$35 / night
SUPERHOST
Entire guesthouse
Chez Bienvenu
3 guests1 bedroom2 beds1 bath
WifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$67 / night
Plus
Entire apartment
Get a Little Glam in a Retro Palm Beach-Style Boudoir
2 guests1 bedroom1 bed1 bath
WifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$60 / night
SUPERHOST
Entire guesthouse
#8 WELCOME HOME IN WINTER PARK
2 guestsStudio1 bed1 bath
WifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$69 / night
SUPERHOST
Entire house
Winter Park/Baldwin Park Oasis- Lake Front w/ Pool
9 guests4 bedrooms6 beds3.5 baths
PoolWifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$200 / night
SUPERHOST
Entire guest suite
Winter Park Suite with Private Entrance & Kitchen
2 guests1 bedroom1 bed1 bath
WifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$75 / night
SUPERHOST
Entire guest suite
The Tree House @ Oasis in Orlando
2 guests1 bedroom1 bed1 bath
WifiFree parkingAir conditioning
Includes cancellation flexibility
Price:$49 / night
1 20 of 300+ places to stay
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