Florida Scenic View base64Hash Florida Scenic View

Winter Park Vacation Rentals

Anytime
1 guest
Anytime
1 guest
Choose from 215 vacation rentals and homes for your trip!

Best-rated vacation rentals in Winter Park

Discover vacation rentals with top-notch guest ratings

House Winter Park
from $112 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding(51 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $265 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(45 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $175 per night
House ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding(37 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal

Pet-friendly rentals in Winter Park

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

House Winter Park
from $271 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(18 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
Vrbo
View deal
House Winter Park
from $185 per night
House ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding(28 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
Vrbo
View deal
House Winter Park
from $258 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent(9 ratings)
Winter Park, Orange County, Florida, United States
Pet-friendly
Vrbo
View deal
See all pet-friendly offers

Vacation rentals with pool in Winter Park

Discover best cabin and house rentals with pool in Winter Park

Apartment Winter Park
from $216 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(8 ratings)
Winter Park, Orange County, Florida, United States
Pool
Vrbo
View deal
House Winter Park
from $235 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding(46 ratings)
Winter Park, Orange County, Florida, United States
Pool
Vrbo
View deal
House Winter Park
from $383 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(8 ratings)
Winter Park, Orange County, Florida, United States
Pool
Vrbo
View deal
See all offers with pool

Best vacation rental offers in Winter Park

House Winter Park
from $331 per night
House ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent(15 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Apartment Winter Park
from $161 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding(31 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $239 per night
House ∙ 8 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Apartment Winter Park
from $177 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
5.0
Outstanding(125 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Apartment Winter Park
from $161 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding(36 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $197 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(27 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $105 per night
House ∙ 4 guests ∙ 3 bedrooms
5.0
Outstanding(4 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $164 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(1 rating)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Cottage Winter Park
from $155 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding(33 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $101 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(2 ratings)
Winter Park, Orange County, Florida, United States
HomeToGo
View deal
House Winter Park
from $240 per night
House ∙ 7 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
HomeToGo
View deal
House Winter Park
from $254 per night
House ∙ 8 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $148 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(3 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $323 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(4 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Condo Winter Park
from $137 per night
Condo ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(2 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $123 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(8 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $200 per night
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $150 per night
House ∙ 6 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $170 per night
House ∙ 8 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Condo Winter Park
from $286 per night
Condo ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding(40 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Apartment Winter Park
from $120 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $119 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(2 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $290 per night
House ∙ 8 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Condo Winter Park
from $137 per night
Condo ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(2 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Apartment Winter Park
from $186 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Villa Winter Park
from $121 per night
Villa ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $127 per night
House ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Vrbo
View deal
House Winter Park
from $211 per night
House ∙ 6 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
Agoda
View deal
Apartment Winter Park
from $132 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(4 ratings)
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Condo Winter Park
from $439 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Vrbo
View deal
Show all 212 apartments in Winter Park
26,766 reviews
26,766 travelers who stayed in Winter Park rated their vacation home 4.5/5 stars on average.

And we love our apartments

House
74 m² Apartment
House
Apartment
74 m² Apartment
Show all 212 apartments in Winter Park

Features of Winter Park vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Pets allowed, Pool and Internet
🏊  Vacation rentals with a pool 69 rentals
🌙 Minimum price starting at $102
🐾 Pet friendly vacation homes 101 rentals
🏡 Rentals available 215 rentals

Other Popular Vacation Destinations

Interesting destinations to consider for your next trip

Destinations worth visiting near Winter Park

image-tag