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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Flat in Winter Park
Tipsy Fox @ Downtown Winter Park Near the Slopes!
1 bedroom, 2 beds, 1 private bathroom
20–25 Sept
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4.95 out of 5 average rating, 162 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
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
Guest favourite
Home in Winter Park
WP Resort Villa 402 - Hot Tub - Arcade - Views
3 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept
4.85 out of 5 average rating, 41 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
Superhost
Home in Winter Park
WP Resort Villa 509 - Hot Tub - Views - Theatre
4 bedrooms, 6 beds, 4.5 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Flat in Winter Park
Hip Ski Pad • Hot Tub • Steps to Downtown
2 beds, 1 bathroom
20–25 Sept
4.85 out of 5 average rating, 39 reviews
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Apartment in Winter Park
Winter Park Condo on the River: Walk to Downtown!
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 123 reviews
Top guest favourite
Home in Fraser
Spacious Cabin with Views • Location • Hot Tub
3 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 174 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
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
Home in Winter Park
Downtown WP Penthouse 221 I Private Hot Tub I View
3 bedrooms, 7 beds, 3 bathrooms
15–20 Sept
4.91 out of 5 average rating, 11 reviews
Luxe
Home in Winter Park
Hike. Bike. Fish. Rooftop Infrared Sauna & Hot Tub
5 bedrooms, 8 beds, 5.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Winter Park
Trailside Escape With a Private Hot Tub!
2 bedrooms, 5 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Winter Park
Duplex In town! Views! PrvtHottub,2Cgarage,Sleeps9
3 bedrooms, 6 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Winter Park
*NEW* Luxe Waterfront Condo in Winter Park
3 bedrooms, 5 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 45 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
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