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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Home in Winter Park
Pool Access & Mtn View! Luxe WP Cabin, Near Trails
3 bedrooms, 3 beds, 2 private bathrooms
21–26 Sept
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4.99 out of 5 average rating, 156 reviews
Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds
14–19 Sept
4.92 out of 5 average rating, 78 reviews
Top guest favourite
Guest suite in Fraser
Madge’s Studio Pets welcome!
1 bedroom, 1 king bed
30 Oct – 4 Nov
4.97 out of 5 average rating, 505 reviews
Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds
13–18 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds
12–17 Sept
5.0 out of 5 average rating, 27 reviews
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds
8–13 Sept
New place to stay
Top guest favourite
Apartment in Winter Park
New Condo Downtown Winter Park-Close to the Slopes
2 bedrooms, 6 beds
8–13 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Apartment in Winter Park
Beautiful Condo at Winter Park!
1 bedroom
8–13 Sept
4.94 out of 5 average rating, 105 reviews
Guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Fraser
Mountain Cozy | New w/ Hot Tub
2 bedrooms, 4 beds
8–13 Sept
4.96 out of 5 average rating, 94 reviews
Top guest favourite
Home in Winter Park
Winter Park Home | Hot Tub Sauna Walk to Downtown
4 bedrooms, 5 beds
6–11 Oct
5.0 out of 5 average rating, 18 reviews
Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds
8–13 Sept
4.87 out of 5 average rating, 119 reviews
Top guest favourite
Home in Fraser
Spacious Cabin with Views • Location • Hot Tub
3 bedrooms, 7 beds
8–13 Sept
4.95 out of 5 average rating, 174 reviews
Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds
12–17 Sept
4.87 out of 5 average rating, 122 reviews
Guest favourite
Townhouse in Winter Park
Modern/Rustic 2-bedroom Townhouse + Bonus Loft
2 bedrooms, 3 beds
22–27 Sept
4.97 out of 5 average rating, 202 reviews
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds
13–18 Sept
4.94 out of 5 average rating, 72 reviews
Top guest favourite
Apartment in Fraser
Updated Fraser Condo | Trails, Shuttle & W/D
1 bedroom, 2 beds
3–8 Oct
4.98 out of 5 average rating, 171 reviews
Top guest favourite
Townhouse in Winter Park
Winter Park Townhome w/ Stunning Slope Views!
3 bedrooms, 6 beds
14–19 Sept
4.94 out of 5 average rating, 163 reviews
Guest favourite
Townhouse in Winter Park
Beautiful Townhome in Downtown Winter Park!
4 bedrooms, 7 beds
8–13 Oct
4.9 out of 5 average rating, 234 reviews