300+ stays
Stays in Winter Park

More than 10,000 guests have stayed in Winter Park.
On average they rated their stays 4.9 out of 5 stars.
SUPERHOST
Entire residential home in Winter Park
Park Ave Lux, Country Feel
4 guests2 bedrooms3 beds2 baths
Free parkingAir conditioningWifi
$155 per night
SUPERHOST
Entire cottage in Winter Park
Cornell Cottage - Quaint & Cozy w/Outdoor Kitchen
2 guestsStudio1 bed1 bath
Free parkingAir conditioningWifi
$69 per night
SUPERHOST
Entire rental unit in Winter Park
Apt F -Modern Elegance in the Heart of Winter Park
4 guests2 bedrooms2 beds1 bath
PoolFree parkingAir conditioningWifi
$79 per night
SUPERHOST
Entire guesthouse in Winter Park
#8 WELCOME HOME IN WINTER PARK
2 guestsStudio1 bed1 bath
Free parkingAir conditioningWifi
$73 per night
SUPERHOST
Entire guest suite in Winter Park
Winter Park Suite with Private Entrance & Kitchen
2 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifi
$90 per night
SUPERHOST
Entire guesthouse in Orlando
The Shed in Downtown Orlando
2 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifi
$67 per night
Entire bungalow in Winter Park
Winter Park/College Park Cozy 2/2 Bungalow
5 guests2 bedrooms2 beds2 baths
Free parkingAir conditioningWifi
$81 per night
SUPERHOST
Entire bungalow in Winter Park
The Garden Room
4 guests1 bedroom2 beds1 bath
Free parkingAir conditioningWifi
$134 per night
SUPERHOST
Entire residential home in Winter Park
Winter Park Oasis A
5 guests3 bedrooms4 beds2 baths
Free parkingAir conditioningWifi
$145 per night
PLUS
Entire rental unit in Winter Park
Get a Little Glam in a Retro Palm Beach-Style Boudoir
2 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifi
$111 per night
SUPERHOST
Entire guest suite in Winter Park
Balfour Palms
2 guestsStudio1 bed1 bath
Free parkingAir conditioningWifi
$75 per night
SUPERHOST
Entire guesthouse in Winter Park
Winter Park Oasis B
5 guests2 bedrooms3 beds1 bath
Free parkingAir conditioningWifi
$152 per night
SUPERHOST
Entire condominium (condo) in Winter Park
LONG STAYS WELCOME
4 guests1 bedroom2 beds1 bath
PoolFree parkingAir conditioningWifi
$79 per night
SUPERHOST
Entire townhouse in Winter Park
Beautiful Downtown Winter Park
3 guests1 bedroom1 bed2 baths
Free parkingAir conditioningWifi
$99 per night
SUPERHOST
Entire residential home in Winter Park
Leave Your Mark, In The Heart Of Winter Park.
2 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifi
$120 per night
SUPERHOST
Entire rental unit in Winter Park
Just 3 Blocks to Shops/Restaurants on Park Ave!
6 guests3 bedrooms4 beds2.5 baths
PoolFree parkingAir conditioningWifi
$140 per night
SUPERHOST
Entire guesthouse in Orlando
Beautiful 1 Bed/1 Bath in College Park Orlando
3 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifi
$80 per night
Entire rental unit in Winter Park
Spacious and Private in lovely Winter Park Orlando
4 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifi
$52 per night
Entire guest suite in Winter Park
Winter Park Getaway
2 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifi
$79 per night
SUPERHOST
Entire guest suite in Winter Park
East End Escape
2 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifi
$105 per night
1 – 20 of 300+ places to stay
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