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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Apartment in Winter Park
Top floor, larger 1 bedroom in Winter Park Village
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
,
4.96 out of 5 average rating, 164 reviews
Guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds, 4 bathrooms
13–18 Sept
4.97 out of 5 average rating, 33 reviews
Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds, 2 bathrooms
12–17 Sept
4.87 out of 5 average rating, 120 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds, 3.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds, 4 bathrooms
12–17 Sept
4.75 out of 5 average rating, 20 reviews
Home in Fraser
Luxe Home w/ Hot Tub, Close to Winter Park Resort!
4 bedrooms, 9 beds, 3.5 bathrooms
8–13 Sept
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
1–6 Sept
New place to stay
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
New place to stay
Guest favourite
Apartment in Winter Park
Luxe 4BR Winter Park Retreat w/ Private Hot Tub
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
4.91 out of 5 average rating, 64 reviews
Superhost
Home in Winter Park
Downtown WP Villa 165 - Hot Tub - Views - Bunks
4 bedrooms, 7 beds, 5.5 bathrooms
1–6 Sept
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Fraser
3 BD/3 BA + BunkRoom + Top Floor Spa + MTN Views
4 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
4.96 out of 5 average rating, 105 reviews
Top guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Apartment in Winter Park
10 Minute Walk to the Winter Park Gondola 6 beds.
3 bedrooms, 6 beds, 2.5 bathrooms
15–20 Oct
4.94 out of 5 average rating, 69 reviews
Guest favourite
Townhouse in Winter Park
Row 41 | 4BR, Rooftop Hot Tub, Walk to Town
4 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.86 out of 5 average rating, 21 reviews
Superhost
Home in Winter Park
Luxury 5BR Winter Park Cabin w/ Hot Tub & Firepit
5 bedrooms, 8 beds, 4.5 bathrooms
8–13 Sept
4.87 out of 5 average rating, 54 reviews
Superhost
Home in Winter Park
Ramble Retreat I Downtown Winter Park w/Hot Tub
4 bedrooms, 7 beds, 4.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds, 4 bathrooms
6–11 Sept
5.0 out of 5 average rating, 31 reviews