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Search results; Over 1,000 homes in Winter Park

Superhost
Apartment in Winter Park
Fraser Crossing 3302 Spacious 2 bed walk to slopes
2 bedrooms, 3 beds, 2 private bathrooms
19–24 Sept
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4.89 out of 5 average rating, 9 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 28 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
Home in Fraser
New Winter Park Townhouse with Great Views!
4 bedrooms, 5 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Winter Park
Après Above It All | Rooftop Hot Tub I Walkable
4 bedrooms, 5 beds, 3.5 bathrooms
15–20 Sept
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
15–20 Sept
New place to stay
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, 19 reviews
Guest favourite
Townhouse in Winter Park
Luxury Ski in/Ski out town home, private hot tub
4 bedrooms, 5 beds, 4.5 bathrooms
16–21 Sept
4.92 out of 5 average rating, 63 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
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds, 4 bathrooms
11–16 Oct
4.77 out of 5 average rating, 22 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
Apartment in Winter Park
Condo w/ Mountain Views in Heart of Downtown!
3 bedrooms, 5 beds, 2 bathrooms
16–21 Sept
4.94 out of 5 average rating, 93 reviews
Guest favourite
Home in Winter Park
Family Friendly! 6BR/Sleeps 16/King Beds. Hot Tub!
6 bedrooms, 15 beds, 3.5 bathrooms
21–26 Sept
4.93 out of 5 average rating, 91 reviews
Top guest favourite
Apartment in Fraser
Bright Modern Mountain Getaway | Views + Garage
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 50 reviews
Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
4.87 out of 5 average rating, 123 reviews
Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 164 reviews
Guest favourite
Home in Fraser
Lux Townhome • Ski Bus • Hot Tub • 2-Car Garage
3 bedrooms, 6 beds, 3.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Winter Park
Cozy DT condo mins from slopes
2 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 106 reviews