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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Apartment in Winter Park
Ski In/Ski Out - Modern Cozy Condo in Winter Park
Studio, 2 beds, 1 private bathroom
20–25 Sept
,
4.9 out of 5 average rating, 247 reviews
Guest favourite
Townhouse in Winter Park
Cozy Mountain Cabin in the Heart of Winter Park
3 bedrooms, 6 beds
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
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
28 Sept – 3 Oct
4.9 out of 5 average rating, 153 reviews
Top guest favourite
Guest suite in Fraser
The Mountains are calling!
1 queen bed
11–16 Oct
4.92 out of 5 average rating, 704 reviews
Top guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds
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
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
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
14–19 Sept
New place to stay
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds
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
15–20 Sept
4.92 out of 5 average rating, 63 reviews
Guest favourite
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds
11–16 Oct
4.77 out of 5 average rating, 22 reviews
Guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds
10–15 Oct
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Apartment in Fraser
Bright Modern Mountain Getaway | Views + Garage
2 bedrooms, 4 beds
14–19 Sept
5.0 out of 5 average rating, 50 reviews
Luxe
Home in Winter Park
Sleeps 19 | Winterhaven Estate by AvantStay
11 bedrooms, 16 beds
15–20 Sept
4.84 out of 5 average rating, 25 reviews
Guest favourite
Apartment in Fraser
Alpine Luxe Loft- Hot Tub, Fireplace, Views, Ski
3 bedrooms, 4 beds
1–6 Nov
4.91 out of 5 average rating, 33 reviews
Top guest favourite
Home in Winter Park
Winter Park Home | Hot Tub Sauna Walk to Downtown
4 bedrooms, 5 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 18 reviews
Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds
27 Sept – 2 Oct
4.87 out of 5 average rating, 123 reviews
Superhost
Cabin in Winter Park
Cozy Cabin in Perfect Location
2 beds
7–12 Oct
4.84 out of 5 average rating, 653 reviews