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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Apartment in Winter Park
Best Views In WinterPark | FamilyFriendly | Garage
3 bedrooms, 6 beds, 3 private bathrooms
19–24 Sept
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5.0 out of 5 average rating, 130 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
Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds, 3 bathrooms
28 Sept – 3 Oct
4.92 out of 5 average rating, 78 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
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
15–20 Sept
4.94 out of 5 average rating, 72 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
Apartment in Fraser
Meadow Ridge Retreat | Near Winter Park
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
New place to stay
Guest favourite
Apartment in Winter Park
One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.88 out of 5 average rating, 221 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, 19 reviews
Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.87 out of 5 average rating, 119 reviews
Top guest favourite
Home in Winter Park
*NEW* Luxe Waterfront Condo in Winter Park
3 bedrooms, 5 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 45 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
Guest favourite
Home in Winter Park
Downtown WP Condo 2203 - Hot Tub - Views - Firepit
2 bedrooms, 2 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 29 reviews
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
21–26 Sept
New place to stay
Top guest favourite
Apartment in Fraser
Updated Fraser Condo | Trails, Shuttle & W/D
1 bedroom, 2 beds, 1 bathroom
3–8 Oct
4.98 out of 5 average rating, 172 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
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
Superhost
Home in Winter Park
Après Above It All | Rooftop Hot Tub I Walkable
4 bedrooms, 5 beds, 3.5 bathrooms
15–20 Sept
Top guest favourite
Flat in Winter Park
NEW Ski In/Out Condo w/ Hot Tub & Balcony
2 bedrooms, 4 beds, 1 bathroom
29 Sept – 4 Oct
5.0 out of 5 average rating, 52 reviews