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Search results; Over 1,000 homes in Winter Park

Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 private bathroom
14–19 Sept
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4.94 out of 5 average rating, 164 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
Cozy Mountain Cabin in the Heart of Winter Park
3 bedrooms, 6 beds, 2.5 bathrooms
14–19 Sept
4.82 out of 5 average rating, 192 reviews
Guest favourite
Home in Fraser
New Winter Park Townhouse with Great Views!
4 bedrooms, 5 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 6 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
Top guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
14–19 Sept
New place to stay
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
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
New place to stay
Top guest favourite
Apartment in Winter Park
Downtown Mtn Oasis + Hot Tubs | Steps to Events
2 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
4.96 out of 5 average rating, 114 reviews
Top guest favourite
Apartment in Fraser
Bright Modern Mountain Getaway | Views + Garage
2 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 50 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
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
14–19 Sept
4.94 out of 5 average rating, 72 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
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
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 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
Luxe
Home in Winter Park
Sleeps 19 | Winterhaven Estate by AvantStay
11 bedrooms, 16 beds, 8 bathrooms
15–20 Sept
4.84 out of 5 average rating, 25 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