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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
9–14 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
13–18 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Flat in Winter Park
The real Winter Park/Alpine experience condo
1 bedroom, 2 beds
6–11 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds
7–12 Sept
4.86 out of 5 average rating, 117 reviews
Home in Winter Park
The Grand Den | Rooftop Spa, Garage & Superb Views
4 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds
9–14 Sept
New place to stay
Superhost
Home in Winter Park
Chalet Apres | Amazing Location | Hot Tub & Sauna
2 bedrooms, 3 beds
3–8 Sept
4.75 out of 5 average rating, 24 reviews
Top guest favourite
Apartment in Fraser
Bright Modern Mountain Getaway | Views + Garage
2 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 49 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
Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds
4–9 Sept
5.0 out of 5 average rating, 70 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, 26 reviews
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds
6–11 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
13–18 Sept
4.92 out of 5 average rating, 63 reviews
Guest favourite
Apartment in Fraser
Mountain Retreat | Private Hot Tub | Sleeps Eight
2 bedrooms, 4 beds
6–11 Sept
4.92 out of 5 average rating, 13 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, 502 reviews
Guest favourite
Guest suite in Winter Park
New Look! Breakfast, Hot Tub & No Host fee!
1 bedroom, 1 king bed
12–17 Sept
4.84 out of 5 average rating, 469 reviews
Top guest favourite
Flat in Winter Park
New Hike or Ski in/out Modern Condo-Quiet w/ Views
2 bedrooms, 4 beds
9–14 Sept
5.0 out of 5 average rating, 42 reviews
Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds
6–11 Sept
4.86 out of 5 average rating, 21 reviews
Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds
8–13 Sept
4.97 out of 5 average rating, 86 reviews