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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Apartment in Winter Park
Top Floor Condo Steps From Free Shuttle w/Hot Tub
2 bedrooms, 2 beds, 2 private bathrooms
13–18 Sept
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4.93 out of 5 average rating, 287 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 28 reviews
Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
4.87 out of 5 average rating, 123 reviews
Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.86 out of 5 average rating, 22 reviews
Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds, 4 bathrooms
11–16 Oct
4.97 out of 5 average rating, 36 reviews
Guest favourite
Townhouse in Winter Park
Modern/Rustic 2-bedroom Townhouse + Bonus Loft
2 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
4.97 out of 5 average rating, 203 reviews
Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
4.92 out of 5 average rating, 78 reviews
Top guest favourite
Home in Winter Park
Winter Park Home | Hot Tub Sauna Walk to Downtown
4 bedrooms, 5 beds, 3.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 18 reviews
Guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds, 4 bathrooms
10–15 Oct
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
4.97 out of 5 average rating, 87 reviews
Guest favourite
Home in Winter Park
Downtown WP Cabin 44 - Hot Tub - Views - Bunks
2 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.96 out of 5 average rating, 78 reviews
Guest favourite
Townhouse in Winter Park
Luxury Ski in/Ski out town home, private hot tub
4 bedrooms, 5 beds, 4.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 63 reviews
Guest favourite
Townhouse in Winter Park
Beautiful Townhome in Downtown Winter Park!
4 bedrooms, 7 beds, 4 bathrooms
8–13 Oct
4.9 out of 5 average rating, 234 reviews
Top guest favourite
Apartment in Fraser
Walk to Restaurants! Peak Leaf Peeping!
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 148 reviews
Guest favourite
Home in Winter Park
Downtown WP Penthouse 221 I Private Hot Tub I View
3 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
4.9 out of 5 average rating, 10 reviews
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Apartment in Winter Park
Private Hot Tub + Free Shuttle | Walk Downtown
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Winter Park
Lux 8000SQ Ft, 9 BDR, 15 Beds, Hot Tub, Lrg Grps
9 bedrooms, 15 beds, 7 bathrooms
28 Sept – 3 Oct
4.9 out of 5 average rating, 153 reviews
Guest favourite
Apartment in Winter Park
Winter Park Condo w/ Fireplace - 4 Mi to Slopes!
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 165 reviews