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300+ stays

Stays in Winter Park

More than 9,000 guests have stayed in Winter Park.
On average they rated their stays 4.9 out of 5 stars.
Entire house in Winter Park
Winter Park - Location! Cutest House!
4 guests2 bedrooms1 bed1 bath
Air conditioningSelf check-inWifiFree parking
Rating 4.83 out of 5;18 reviews
Price:$174 / night
SUPERHOST
Entire guest suite in Winter Park
East End Escape - (Contactless Check-In & Out)
2 guests1 bedroom2 beds1 bath
Air conditioningSelf check-inWifiFree parking
Rating 4.95 out of 5;132 reviews
Price:$83 / night
SUPERHOST
Tiny house in Orlando
The Little Treehouse 2 at Country Club of Orlando
2 guestsStudio1 bed1 bath
Indoor fireplaceBreakfastAir conditioningSelf check-in
Rating 5.0 out of 5;186 reviews
Price:$92 / night
SUPERHOST
Entire apartment in Winter Park
Luxury Downtown Winter Park Guesthouse
2 guests1 bedroom1 bed1 bath
Air conditioningSelf check-inWifiFree parking
Rating 4.90 out of 5;119 reviews
Price:$160 / night
SUPERHOST
Entire guesthouse in Winter Park
Winter Park Oasis
5 guests2 bedrooms3 beds1 bath
Air conditioningWifiPets allowedFree parking
Rating 4.91 out of 5;11 reviews
Price:$130 / night
SUPERHOST
Entire guest suite in Winter Park
Balfour Palms
2 guestsStudio1 bed1 bath
Air conditioningSelf check-inWifiFree parking
Rating 4.95 out of 5;56 reviews
Price:$56 / night
SUPERHOST
Entire guest suite in Winter Park
Winter Park Suite with Private Entrance & Kitchen
2 guests1 bedroom1 bed1 bath
Air conditioningSelf check-inWifiFree parking
Rating 4.99 out of 5;107 reviews
Price:$75 / night
SUPERHOST
Entire house in Winter Park
Luxurious Stay in the Heart of Winter Park
6 guests3 bedrooms3 beds2 baths
Air conditioningSelf check-inWifiFree parking
Rating 4.92 out of 5;12 reviews
Price:$193 / night
SUPERHOST
Entire guesthouse in Orlando
The Shed in Downtown Orlando
2 guests1 bedroom1 bed1 bath
Air conditioningSelf check-inWifiKitchen
Rating 4.97 out of 5;273 reviews
Price:$58 / night
SUPERHOST
Entire house in Orlando
8th Green Cottage - A relaxing oasis in the city
4 guests2 bedrooms3 beds1 bath
Air conditioningSelf check-inWifiPets allowed
Rating 5.0 out of 5;13 reviews
Price:$85 / night
Entire house in Winter Park
Live Like a Real Celebrity in Artsy Winter Park!
6 guests2 bedrooms3 beds2 baths
Air conditioningSelf check-inWifiFree parking
Price:$375 / night
SUPERHOST
Entire guesthouse in Winter Park
Winter Park Bungalow
2 guests1 bedroom1 bed1 bath
Air conditioningSelf check-inWifiFree parking
Rating 4.93 out of 5;60 reviews
Price:$70 / night
Entire guesthouse in Winter Park
Winter Park Private Quaint Guest House
2 guestsStudio1 bed1 bath
BreakfastAir conditioningWifiPets allowed
Rating 4.65 out of 5;232 reviews
Price:$63 / night
Entire guesthouse in Orlando
Oasis Garden Cottage -cozy, chic, near everything!
5 guests1 bedroom1 bed1 bath
Indoor fireplaceBreakfastAir conditioningSelf check-in
Rating 5.0 out of 5;40 reviews
Price:$66 / night
SUPERHOST
Entire loft in Orlando
Downtown (Ivanhoe Village) Loft Apartment
2 guests1 bedroom1 bed1 bath
Air conditioningSelf check-inWifiFree parking
Rating 4.85 out of 5;552 reviews
Price:$61 / night
PLUS
Entire apartment in Winter Park
Get a Little Glam in a Retro Palm Beach-Style Boudoir
2 guests1 bedroom1 bed1 bath
Air conditioningSelf check-inWifiFree parking
Rating 4.94 out of 5;111 reviews
Price:$96 / night
SUPERHOST
Private room in Orlando
Private Master Suite in College Park, Orlando FL
2 guests1 bedroom1 bed1 private bath
Air conditioningSelf check-inWifiFree parking
Rating 4.99 out of 5;146 reviews
Price:$33 / night
SUPERHOST
Entire guesthouse in Maitland
Chez Bienvenu
3 guests1 bedroom2 beds1 bath
Air conditioningWifiPets allowedFree parking
Rating 4.87 out of 5;285 reviews
Price:$68 / night
SUPERHOST
Entire apartment in Orlando
Stylish Dbl Suite Nr Downtown, MCO, Disney, Amway
6 guests2 bedrooms2 beds2 baths
BreakfastAir conditioningSelf check-inWifi
Rating 4.88 out of 5;17 reviews
Price:$100 / night
SUPERHOST
Entire guesthouse in Winter Park
#8 WELCOME HOME IN WINTER PARK
2 guestsStudio1 bed1 bath
Air conditioningSelf check-inWifiFree parking
Rating 4.82 out of 5;159 reviews
Price:$72 / night
1 20 of 300+ places to stay
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