Vacation rentals in Winter Park
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Top-rated vacation rentals in Winter Park
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Winter Park vacation rentals
Other great vacation rentals in Winter Park
Condo in Winter Park
4.93 out of 5 average rating, 115 reviewsMinutes from the lifts, seconds from the hot tub.
Jun. 6 – 13
Condo in Winter Park
4.88 out of 5 average rating, 100 reviewsTop-Floor Condo | On Ski Bus Route | Pool, Hot Tub
Nov. 26 – Dec. 3
Condo in Winter Park
4.91 out of 5 average rating, 111 reviewsSki In/Ski Out - Modern Cozy Condo in Winter Park
May 18 – 25
Condo in Winter Park
5.0 out of 5 average rating, 304 reviewsWinter Park Studio: On the River~ Walk Downtown!
Sep. 4 – 11
Condo in Winter Park
4.88 out of 5 average rating, 212 reviewsWinter Park Studio: Resort Access, Mountain Charm
May 22 – 29
Apartment in Winter Park
4.81 out of 5 average rating, 124 reviewsLovely one bedroom Apartment in an Aspen forest.
Jun. 14 – 21
Condo in Winter Park
4.86 out of 5 average rating, 84 reviewsStudio Condo in the Heart of Winter Park! lic#9602
May 25 – Jun. 1
Condo in Winter Park
4.97 out of 5 average rating, 87 reviewsTop floor, larger 1 bedroom in Winter Park Village
Oct. 21 – 28
Quick stats about vacation rentals in Winter Park
Total rentals
1.4K properties
Rentals with a pool
570 properties have a pool
Pet-friendly rentals
190 properties allow pets
Family-friendly rentals
1K properties are a good fit for families
Total number of reviews
37K reviews
Nightly prices starting at
$68 CAD before taxes and fees
Destinations to explore
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- Fitness-friendly rentals Winter Park
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- Ski-in/ski-out rentals Winter Park
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