Vacation rentals in Winter Park, United States

Carefully selected & verified rentals in Winter Park, United States
Check-in
27Jun2025Select date
Check-out
28Jun2025Select date
Rooms and Guests2 Guests, 1 Room
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141-160 out of 256
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
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
Zephyr Mountain Lodge Premium-Rated 2516
Map800 yd from City Centre100 yd from Zephyr Express
Select
Iron Horse C4093 Condo
Map1500 yd from City Centre500 yd from Cabriolet
FromUS$ 477 /nightSelect
Value Unit 4440 - Two Bedroom - Fraser Crossing Founders Pointe Condo
Map900 yd from City Centre300 yd from Winter Park Resort
FromUS$ 1 191 /nightSelect
Winter Park Condo With Resort Shuttle On-Site!
Map1.9 mi from City Centre300 yd from
FromUS$ 101 /nightSelect
Premium Unit 4466 - One Bedroom Withkitchenette - Fraser Crossing Founders Pointe Condo
Map900 yd from City Centre300 yd from Winter Park Resort
FromUS$ 492 /nightSelect
Premium Unit 4568 - One Bedroom Withkitchenette - Fraser Crossing Founders Pointe Condo
Map900 yd from City Centre300 yd from Winter Park Resort
FromUS$ 551 /nightSelect
Convenient Winter Park Condo - 3 Mi To Resort!
Map1.8 mi from City Centre300 yd from
Select
Winter Park Base Area Condo - Fraser Crossing Founders Pointe Premium Unit 3406 Condo
Map900 yd from City Centre300 yd from Winter Park Resort
FromUS$ 456 /nightSelect
Crisp Mountain Retreat
Map2.0 mi from City Centre300 yd from
FromUS$ 217 /nightSelect
Secluded Condo With Corridor Ski Trail View - Zephyr Mountain Lodge Premium Unit 1201 Condo
Map800 yd from City Centre100 yd from Zephyr Express
Select
Downtown Winter Park Condo With Free Bus To Ski Base
Map2.6 mi from City Centre200 yd from Amaze'n Mazes Colorado
FromUS$ 171 /nightSelect
Condo With Mountain Views In Heart Of Downtown!
Map2.1 mi from City Centre700 yd from
FromUS$ 969 /nightSelect
Alpine Hideaway Condo
Map2.7 mi from City Centre300 yd from Amaze'n Mazes Colorado
Select
Gorgeous Winter Park Condo With Private Deck!
Map2.0 mi from City Centre100 yd from
FromUS$ 198 /nightSelect
Winter Park Condo With Balcony And Mtn Views!
Map2.4 mi from City Centre800 yd from
FromUS$ 236 /nightSelect
Ski Retreat With Hot Tub Access In Winter Park!
Map2.0 mi from City Centre300 yd from
FromUS$ 180 /nightSelect
Premium Unit 1108 - One Bedroom - Zephyr Mountain Lodge Condo
Map800 yd from City Centre100 yd from Zephyr Express
Select

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
27Jun2025Select date
Check-out
28Jun2025Select date
Rooms and Guests2 Guests, 1 Room