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Search results; Over 1,000 homes in Winter Park

Top guest favorite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 bed, 1 private bath
Aug 23 – 28
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4.98 out of 5 average rating, 497 reviews
Guest favorite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds, 4 baths
Aug 16 – 21
4.97 out of 5 average rating, 32 reviews
Top guest favorite
Cabin in Grand County
Scandinavian-Inspired Escape: Modern Cabin w/ Spa
3 bedrooms, 5 beds, 2 baths
Sep 6 – 11
4.96 out of 5 average rating, 292 reviews
Guest favorite
Apartment in Fraser
Eagle Ridge above the summit
2 bedrooms, 3 beds, 2 baths
Aug 16 – 21
5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Winter Park
Downtown WP Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds, 4 baths
Sep 12 – 17
4.79 out of 5 average rating, 19 reviews
Apartment in Winter Park
The real Winter Park/Alpine experience condo
1 bedroom, 2 beds, 1 bath
Aug 18 – 23
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Home in Winter Park
Winter Park Home | Hot Tub Sauna Walk to Downtown
4 bedrooms, 5 beds, 3.5 baths
Aug 16 – 21
5.0 out of 5 average rating, 16 reviews
Top guest favorite
Condo in Fraser
View • Fireplace • Hot Tub • Sauna • Pool
2 bedrooms, 5 beds, 2.5 baths
Aug 23 – 28
4.98 out of 5 average rating, 329 reviews
Guest favorite
Condo in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 bath
Aug 13 – 18
4.94 out of 5 average rating, 161 reviews
Guest favorite
Home in Winter Park
WP Resort Villa 402 - Hot Tub - Arcade - Views
3 bedrooms, 8 beds, 3.5 baths
Aug 16 – 21
4.85 out of 5 average rating, 40 reviews
Top guest favorite
Apartment in Winter Park
Modern New build ski in/out. 1br + den.
1 bedroom, 4 beds, 1 bath
Aug 23 – 28
5.0 out of 5 average rating, 43 reviews
Top guest favorite
Home in Tabernash
Continental Divide Views! New Log Home w/ Hot Tub!
4 bedrooms, 7 beds, 3 baths
Aug 16 – 21
4.98 out of 5 average rating, 108 reviews
Top guest favorite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds, 4 baths
Aug 21 – 26
5.0 out of 5 average rating, 29 reviews
Top guest favorite
Condo in Fraser
Walk to Restaurants! Bike, Hike and Fish!
1 bedroom, 3 beds, 1 bath
Aug 15 – 20
4.97 out of 5 average rating, 144 reviews
Condo in Winter Park
Winter Park Riverfront, Hike, Bike, Walk Downtown
1 bedroom, 2 beds, 1 bath
Aug 25 – 30
New place to stay
Guest favorite
Home in Winter Park
Downtown WP Condo 1409 - Hot Tub - Views - Firepit
2 bedrooms, 4 beds, 2 baths
Aug 14 – 19
4.94 out of 5 average rating, 31 reviews
Top guest favorite
Home in Fraser
Spacious Cabin • Family Friendly • Hot Tub • Views
3 bedrooms, 7 beds, 3.5 baths
Aug 16 – 21
4.95 out of 5 average rating, 173 reviews
Top guest favorite
Apartment in Winter Park
Mountain Town Luxury Penthouse
2 bedrooms, 3 beds, 3 baths
Aug 13 – 18
5.0 out of 5 average rating, 26 reviews
Superhost
Home in Fraser
Downtown WP Villa 168 - Private Hot Tub - Views
3 bedrooms, 4 beds, 3.5 baths
Aug 13 – 18