Search results; Over 1,000 homes in Winter Park

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Top guest favorite
Condo in Winter Park
Slopeside Studio
2 beds
Nov 16 – 21
R7,512 ZAR for 5 nights
5.0 out of 5 average rating, 12 reviews
Guest favorite
Condo in Winter Park
Ski-In Ski-Out Zephyr Mtn Lodge Condo w/ Hot Tub
2 beds
Sep 1 – 6
R11,457 ZAR for 5 nights
4.89 out of 5 average rating, 228 reviews
Apartment in Winter Park
NEW|Ski in/out|VIEWS|Garage Parking|Hot Tub
4 beds
Sep 4 – 9
R18,045 ZAR for 5 nights
New place to stay
Superhost
Condo in Winter Park
Ski-In/Ski-Out Studio Mtn View-Free Heated Parking
2 beds
Sep 9 – 14
R8,411 ZAR for 5 nights
4.85 out of 5 average rating, 79 reviews
Townhouse in Winter Park
Cozy Winter Park Townhome • Hot Tub & Near Resort
4 beds
Sep 1 – 6
R19,493 ZAR for 5 nights
New place to stay
Guest favorite
Condo in Winter Park
Cozy mountain retreat in downtown Winter Park
3 beds
Sep 1 – 6
R10,387 ZAR for 5 nights
4.93 out of 5 average rating, 132 reviews
Guest favorite
Apartment in Winter Park
Cozy Condo- Walk to Winter Park Resort!
2 beds
Sep 3 – 8
R15,330 ZAR for 5 nights
4.91 out of 5 average rating, 46 reviews
Superhost
Condo in Winter Park
Beautiful Cozy Studio at the Base-Heated Parking
2 beds
Sep 9 – 14
R8,370 ZAR for 5 nights
4.78 out of 5 average rating, 329 reviews
Top guest favorite
Condo in Winter Park
Zephyr Ski In/Out at Winter Park - 1/2 Price Tues!
2 beds
Sep 1 – 7
R42,061 ZAR for 6 nights
5.0 out of 5 average rating, 51 reviews
Top guest favorite
Guest suite in Fraser
Spring into summer at Madge’s. Pets welcome!
1 king bed
Oct 26 – 31
R8,584 ZAR for 5 nights
4.96 out of 5 average rating, 443 reviews
Top guest favorite
Apartment in Winter Park
Modern New build ski in/out. 1br + den.
4 beds
Sep 1 – 6
R11,541 ZAR for 5 nights
5.0 out of 5 average rating, 25 reviews
Guest favorite
Condo in Winter Park
Ski In/Ski Out - Modern Cozy Condo in Winter Park
2 beds
Sep 9 – 14
R12,359 ZAR for 5 nights
4.89 out of 5 average rating, 180 reviews
Top guest favorite
Apartment in Winter Park
The Little Palace-Full Amenities
2 beds
Sep 1 – 6
R10,638 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Superhost
Guest suite in Winter Park
New Look! Breakfast, Hot Tub & No Host fee!
1 king bed
Sep 14 – 19
R11,856 ZAR for 5 nights
4.82 out of 5 average rating, 399 reviews
Guest favorite
Condo in Winter Park
One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit
2 beds
Sep 7 – 12
R12,464 ZAR for 5 nights
4.86 out of 5 average rating, 189 reviews
Guest favorite
Apartment in Winter Park
Ski-in Ski-Out Winter Park Condo
Sep 7 – 12
R13,513 ZAR for 5 nights
4.95 out of 5 average rating, 37 reviews
Top guest favorite
Condo in Winter Park
Cozy Winter Park Riverfront Studio~ Walk Downtown
2 beds
Sep 7 – 12
R11,828 ZAR for 5 nights
5.0 out of 5 average rating, 86 reviews
Guest favorite
Condo in Winter Park
2BR Ski-In Ski-Out w/ Desirable Amenities
4 beds
Sep 5 – 10
R16,786 ZAR for 5 nights
5.0 out of 5 average rating, 8 reviews