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.
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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
Guest favourite
Apartment in Winter Park
4.85 out of 5 average rating, 288 reviewsVillage of Winter Park Condo
May 9 – 16
$217Â CAD per night
Guest favourite
Condo in Winter Park
4.92 out of 5 average rating, 110 reviewsSki In/Ski Out - Modern Cozy Condo in Winter Park
May 11 – 18
$272Â CAD per night
Guest favourite
Condo in Winter Park
4.93 out of 5 average rating, 123 reviewsPeaceful place on river with great views
May 26 – Jun. 2
$185Â CAD per night
Guest favourite
Condo in Winter Park
4.93 out of 5 average rating, 114 reviewsMinutes from the lifts, seconds from the hot tub.
Sep. 7 – 14
$241Â CAD per night
Guest favourite
Apartment in Winter Park
4.94 out of 5 average rating, 100 reviewsCalm vibes and a great view the at the Alpen Rose
Aug. 5 – 12
$284Â CAD per night
Guest favourite
Condo in Winter Park
5.0 out of 5 average rating, 30 reviewsSki in Ski Out Cozy Condo
Aug. 14 – 21
$164Â CAD per night
Guest favourite
Condo in Winter Park
5.0 out of 5 average rating, 47 reviewsCozy DT condo mins from slopes
May 22 – 29
$176Â CAD per night
Guest favourite
Condo in Winter Park
4.86 out of 5 average rating, 83 reviewsStudio Condo in the Heart of Winter Park! lic#9602
Nov. 15 – 22
$187Â CAD per night
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
$69Â CAD before taxes and fees
Destinations to explore
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- Monthly Rentals Winter Park
- Rentals with a hot tub Winter Park
- Waterfront rentals Winter Park
- Condo rentals Winter Park
- Cabin rentals Winter Park
- Rentals with pools Winter Park
- Rentals with a firepit Winter Park
- Rentals with a patio Winter Park
- Family-friendly rentals Winter Park
- Townhouse rentals Winter Park
- Rentals with a kayak Winter Park
- Pet-friendly rentals Winter Park
- Rentals with an EV charger Winter Park
- Apartment rentals Winter Park
- Rentals with outdoor seating Winter Park
- Fitness-friendly rentals Winter Park
- Rentals with a fireplace Winter Park
- Rentals with lake access Winter Park
- House rentals Winter Park
- Rentals with a sauna Winter Park
- Kid-friendly rentals Winter Park
- Rentals with a washer and dryer Winter Park
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