Winter Park vacation rentals

We found 1,981 vacation rentals — enter your dates for availability

Select from 527 houses, 977 condos, and other vacation rentals to find the perfect place for your stay in Winter Park. Vacation homes offer the best amenities for you and your friends, family, or even pets, like WiFi and cable TV. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

The cozy city of Winter Park awaits you

Enjoy the live music and other features of Winter Park. Renowned for its skiing, mountain views and snowboarding, this city welcomes all visitors. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Winter Park

Are you looking for attractions to visit during your stay? Travelers enjoy Winter Park for its skiing, snowboarding and hiking. Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Winter Park a fun spot to vacation. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Winter Park Ski Resort (3.7 mi / 5.9 km)
  • Keystone Ski Resort (25.5 mi / 41.1 km)
  • Trestle Bike Park (2.5 mi / 4.1 km)
  • Pole Creek Golf Club (7.7 mi / 12.3 km)
  • Ski Granby Ranch (10.3 mi / 16.6 km)
  • Eldora Mountain Resort (10.7 mi / 17.3 km)

Exploring the mountains and other natural features in Winter Park

Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Winter Park. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Rocky Mountain National Park (29.7 mi / 47.9 km)
  • Saint Mary's Glacier (9.1 mi / 14.7 km)
  • Georgetown Lake (14.1 mi / 22.7 km)
  • Torreys Peak (16 mi / 25.8 km)
  • Lake Granby (16.4 mi / 26.3 km)
  • Loveland Pass (18.4 mi / 29.6 km)

Seasonal weather averages in Winter Park

Winter Park is well known for its skiing. If you're interested in winter sports, you might consider visiting in January, February, March or April, when snowfall averages 26 inches and temperatures average 17°F.

Traveling to and around Winter Park

The nearest airport is in Broomfield, CO (BJC-Rocky Mountain Metropolitan), located 35.7 mi (57.4 km) from the city center.

If you'd prefer to travel by train, the main station serving the city is Winter Park Ski Resort Amtrak Station.

Frequently asked questions

What is the best area to stay in Winter Park when booking a vacation rental?
Old Town Winter Park is one of the more sought-after locations for a vacation property in Winter Park. Spend your stay here to savor the comfort and privacy that comes with having the entire place to yourself.
What is the most popular type of vacation rental accommodation in Winter Park?
The most desirable types of vacation rentals in Winter Park are condos. Prefer something different? Vrbo has numerous options to match our guests’ unique requirements, so you’ll see vacation homes in loads of sizes and shapes. The perfect fit is waiting for you — book yours today.
How much does it cost to rent a vacation rental in Winter Park?
Different factors affect the price of a vacation rental in Winter Park, such as the time of year, length of stay and property type. However, all our vacation homes have something in common — exceptional value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Winter Park?
When you travel and the style and size of the property will determine the cost of your beachside escape. Put in your Winter Park travel dates to see your options on Vrbo. Can’t live without a hot tub, or maybe a private pool? Use the filters to pick the amenities and features you want in your vacation home.
Are there pet-friendly vacation rentals in Winter Park?
Pack a travel bag and a bone for the pup in your life because Winter Park has 598 stays that open their doors to pets. Let your four-legged friend get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Winter Park?
Tick the “pool” box in our handy filter tool and select from 255 houses with private pools in Winter Park on Vrbo. Ball games, gentle soak or noodle joust? Free time is up to you when your Vrbo vacation home comes with a swimming pool.
What are popular rental amenities in Winter Park?
Some of the most popular rental amenities guests are looking for in Winter Park are tennis, a chef and a lake view. Whether you’re traveling with family, buddies or even pets, Vrbo vacation properties feature the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group vacation rentals in Winter Park?
Winter Park has 101 vacation properties that can fit 10 or more people. These properties come with the space and privacy you need to share good times with your nearest and dearest.
Are there vacation rentals in Winter Park that welcome kids?
With 598 family-friendly vacation rentals available in Winter Park, now is a fantastic time to introduce your children to the pleasures of travel. Simply check our “Properties good for families” filter box to view stays packed with amenities perfect for families on the move, such as multiple bedrooms, yards, bunk beds and entertainment areas.
What are the top attractions for families in Winter Park?
There are plenty of amazing things to see and do with the family in Winter Park, including:

  • Amazen Maze Winter Park
  • Moffat Tunnel West Portal
  • Trestle Bike Park

Are there one-bedroom vacation rentals in Winter Park?
You’ll find 106 one-bedroom properties in Winter Park to choose from. A one-bedroom vacation home is a wonderful choice if it’s just you and your partner or if you’re vacationing alone. Toss in more convenience, space and privacy compared to a hotel, and you’re bound to have a memorable trip.
Can I find two-bedroom vacation rentals in Winter Park?
Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 221 two-bedroom vacation properties Winter Park has to offer.
Are there vacation rentals with WiFi in Winter Park?
Whether you want to keep up with the headlines, reply to emails or surf your social networks, there are 157 vacation homes with WiFi in Winter Park. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Winter Park?
You can pick from 27 Vrbo vacation homes with air conditioning in Winter Park giving you that gentle, cool breeze and extra element of comfort. Enter your chosen travel dates and then use our filter tool to search for stays with air conditioning.
How old do you have to be to rent a vacation rental in Winter Park?
We recommend checking with the Winter Park vacation rental you’d like on Vrbo as the minimum age differs. However, it’s generally 16, 18 or 21.
How long can I rent a vacation rental in Winter Park for?
How long you can rent a vacation rental in Winter Park is down to the property. Simply enter your chosen travel dates to look at a list of options offering extended stays. With loads of amenities like laundries and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to get somewhere just right to call your home away from home in Winter Park.

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