Vacation rentals in Winter Park, United States

Carefully selected & verified rentals in Winter Park, United States
Check-in
26Jun2025Select date
Check-out
27Jun2025Select date
Rooms and Guests2 Guests, 1 Room
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101-120 out of 249
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Winter Park Condo With Private Balcony Near Skiing!
Map2.9 mi from City Centre300 yd from
FromUS$ 89 /nightSelect
Ski-In / Ski-Out Studio Condo At The Base Of Winter Park
Map900 yd from City Centre300 yd from Winter Park Resort
FromUS$ 206 /nightSelect
Walk To Winter Park Resort Condo With Hot Tub!
Map100 yd from City Centre700 yd from Arrow
FromUS$ 321 /nightSelect
Great Location! Downtown Wp With Hot Tub! Sleeps 6!
Map2.0 mi from City Centre300 yd from
FromUS$ 104 /nightSelect
Snowblaze A24 Condo
Map2.0 mi from City Centre300 yd from
FromUS$ 368 /nightSelect
Best Location In Downtown Winter Park
Map2.0 mi from City Centre300 yd from
FromUS$ 308 /nightSelect
Winter Park Condo Rental 4 Mi To Ski Resort!
Map2.0 mi from City Centre300 yd from
FromUS$ 292 /nightSelect
Riverfront Cozy Retreat With Hot Tub & Pool
Map2.7 mi from City Centre300 yd from Amaze'n Mazes Colorado
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Winter Park Condo With Gas Grill Walk To Gondola!
Map300 yd from City Centre900 yd from Arrow
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Iron Horse C3013 Condo
Map1400 yd from City Centre400 yd from Cabriolet
FromUS$ 476 /nightSelect
Premium Unit 2801 - Zephyr Mountain Lodge Condo
Map800 yd from City Centre100 yd from Zephyr Express
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Iron Horse C5013 Condo
Map1400 yd from City Centre400 yd from Cabriolet
FromUS$ 352 /nightSelect
Timber Fox 1309 Condo
Map2.1 mi from City Centre700 yd from
FromUS$ 375 /nightSelect
Hi Country Haus 22-8
Map2.7 mi from City Centre400 yd from Amaze'n Mazes Colorado
FromUS$ 209 /nightSelect
Ski Idlewild Condo
Map2.1 mi from City Centre700 yd from
FromUS$ 264 /nightSelect
Premium Unit 4575-Fraser Crossing Founders Pointe Condo
Map900 yd from City Centre300 yd from Winter Park Resort
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3 Mi To Winter Park Resort Condo With Patio And Grill
Map2.2 mi from City Centre700 yd from
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Mountain-View Winter Park Condo With Balcony!
Map2.1 mi from City Centre700 yd from
FromUS$ 431 /nightSelect
Mountain-View Condo In Downtown Winter Park!
Map2.1 mi from City Centre700 yd from
Select
Winter Park Condo With Shuttle To Slopes!
Map2.6 mi from City Centre100 yd from Amaze'n Mazes Colorado
FromUS$ 220 /nightSelect

Flexible Price Range for Vacation Homes in Winter Park

From cozy retreats to luxury villas – Find the ideal stay for every budget

⬆️ The highest price
US$ 2 030
⬇️ The lowest price
US$ 65
đź’¸ Average price for
Apartments
US$ 589

Top vacation homes in Winter Park

Based on guest reviews from the past 12 months

Convenient Downtown Escape:
Guest Suite Downtown Winter Park Great Location
Cozy Mountaintop Retreat:
Ski-In/Ski-Out Zephyr 1 Bedroom Condo Winter Park
Family Friendly Condo Stay:
Winter Park Condo With Hot Tubs, 4 Mi To Ski Resort!
Outdoor Adventure Base:
Cozy Winter Park Condo Bike, Ski, And Hike!
Relaxing Hot Tub Getaway:
Winter Park Condo W/Hot Tub & 4 Mi To Skiing
Scenic Riverfront Stay:
Cozy Condo On Vasquez Creek With Free Shuttle Access
Ski-In Ski-Out Luxury:
Ski-Inandski-Out Winter Park Condo With Mountain Views
Tranquil Mountain Views:
Crisp Mountain Retreat
Charming Rustic Vibe:
Rustic Relaxation In Winter Park

Vacation Rentals Overview in Winter Park

This guide provides essential information on vacation rentals in Winter Park, evaluating around 100 properties to assist travelers in making informed accommodation choices.

Typical nightly rates range from $150-$400 USD.

Peak travel seasons are winter months and summer holidays.

Most properties impose a local tax of 12.8%.

Approximately 1-2 miles from Winter Park Resort and downtown.

Booking early can secure discounts and ensure availability.

Check-in
26Jun2025Select date
Check-out
27Jun2025Select date
Rooms and Guests2 Guests, 1 Room