Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Winter Park vacation rentals

Property entrance

Zephyr Mountain Lodge

Zephyr Mountain Lodge
3.5 star property
Winter Park Village
8.2 out of 10, Very good, (680 reviews)
"Clean room and staff was outstanding. "
United States
Jessica
The price is CA $1,058
CA $1,263 total
includes taxes & fees
Feb 9 - Feb 10
Zephyr Mountain Lodge
Studio | Property grounds

Iron Horse C5083 Studio Bedroom Condo by RedAwning

Iron Horse C5083 Studio Bedroom Condo by RedAwning
3.5 star property
Winter Park
9.0 out of 10, Wonderful, (2 reviews)
"The room was nice. The location was nice. I really enjoyed my time staying there. "
United States
Vicki
The price is CA $248
CA $937 total
includes taxes & fees
Feb 9 - Feb 10
Iron Horse C5083 Studio Bedroom Condo by RedAwning
Apartment

10 min to Resort Amazing Views Sauna

10 min to Resort Amazing Views Sauna
2.0 star property
Winter Park
The price is CA $707
CA $959 total
includes taxes & fees
Feb 13 - Feb 14
10 min to Resort Amazing Views Sauna
Apartment (1 Bedroom) | Interior

Downtown Winter Park Condo: 3 Mi to Slopes!

Downtown Winter Park Condo: 3 Mi to Slopes!
3.5 star property
Winter Park
The price is CA $342
CA $742 total
includes taxes & fees
Feb 17 - Feb 18
Downtown Winter Park Condo: 3 Mi to Slopes!
Condo, 1 Bedroom | Terrace/patio

Ski Idlewild 1 Bedroom Condo by RedAwning

Ski Idlewild 1 Bedroom Condo by RedAwning
3.0 star property
Winter Park
8.0 out of 10, Very good, (1 review)
"Interesting place. Overall, it was a nice place in a good location to walk around. The condo was outfitted better than some other places. The door access code system was a bit fishy. When the door was "locked" via code and not the deadbolt, I was locked out and had to call for help. There is no office on sight (which would be helpful), the nongarage parking was good, the parking garage was built for smart cars, not SUVs (not ideal for a ski town), the hot tub was ok, but would be better to have...
United States
Anonymous traveller
The price is CA $242
CA $912 total
includes taxes & fees
Feb 9 - Feb 10
Ski Idlewild 1 Bedroom Condo by RedAwning
Condo, 1 Bedroom | Exterior

Founders Pointe 1 bedroom Condo by RedAwning

Founders Pointe 1 bedroom Condo by RedAwning
3.0 star property
Winter Park Village
6.0 out of 10, (1 review)
The price is CA $268
CA $895 total
includes taxes & fees
Feb 11 - Feb 12
Founders Pointe 1 bedroom Condo by RedAwning
Condo, 1 Bedroom | Living area

Ski Inn Condo 1 Bedroom Condo

Ski Inn Condo 1 Bedroom Condo
3.0 star property
Old Town Winter Park
The price is CA $289
CA $994 total
includes taxes & fees
Feb 9 - Feb 10
Ski Inn Condo 1 Bedroom Condo
Townhome, 4 Bedrooms | Living area

Base Camp At Iron Horse... 4 Bedroom Townhouse by RedAwning

Base Camp At Iron Horse... 4 Bedroom Townhouse by RedAwning
3.0 star property
Winter Park
The price is CA $810
CA $2,442 total
includes taxes & fees
Feb 9 - Feb 10
Base Camp At Iron Horse... 4 Bedroom Townhouse by RedAwning
Condo, 2 Bedrooms | Living area

Snowblaze A24 2 Bedroom Condo by RedAwning

Snowblaze A24 2 Bedroom Condo by RedAwning
3.0 star property
Winter Park
Snowblaze A24 2 Bedroom Condo by RedAwning
House, 3 Bedrooms | Living area

Antler At Lakota 407 3 Bedroom Home

Antler At Lakota 407 3 Bedroom Home
3.0 star property
Winter Park
The price is CA $820
CA $2,239 total
includes taxes & fees
Feb 25 - Feb 26
Antler At Lakota 407 3 Bedroom Home
House, 4 Bedrooms | Private kitchen

Willows At Grand Park 4 Bedroom Home by RedAwning

Willows At Grand Park 4 Bedroom Home by RedAwning
3.5 star property
Fraser
The price is CA $497
CA $1,873 total
includes taxes & fees
Feb 9 - Feb 10
Willows At Grand Park 4 Bedroom Home by RedAwning
Condo, 2 Bedrooms | Private kitchen

Snowblaze Athletic Club -a11 2 Bedroom Condo by RedAwning

Snowblaze Athletic Club -a11 2 Bedroom Condo by RedAwning
3.0 star property
Winter Park
The price is CA $259
CA $1,148 total
includes taxes & fees
Feb 9 - Feb 10
Snowblaze Athletic Club -a11 2 Bedroom Condo by RedAwning
Condo, 2 Bedrooms | Private kitchen

Cozens Pointe I-101 2 Bedroom Condo by RedAwning

Cozens Pointe I-101 2 Bedroom Condo by RedAwning
3.5 star property
Fraser
The price is CA $854
CA $2,078 total
includes taxes & fees
Feb 13 - Feb 14
Cozens Pointe I-101 2 Bedroom Condo by RedAwning
Condo, 3 Bedrooms | Private kitchen

Aprez Retreat 3 Bedroom Condo by RedAwning

Aprez Retreat 3 Bedroom Condo by RedAwning
3.0 star property
Winter Park
The price is CA $414
CA $1,581 total
includes taxes & fees
Feb 9 - Feb 10
Aprez Retreat 3 Bedroom Condo by RedAwning
Condo, 2 Bedrooms | Living area

Downtown Flat 2 Bedroom Condo

Downtown Flat 2 Bedroom Condo
3.0 star property
Winter Park
The price is CA $295
CA $1,193 total
includes taxes & fees
Feb 10 - Feb 11
Downtown Flat 2 Bedroom Condo
House, 4 Bedrooms | Living area

Mountain Willow At Grand Park 4 Bedroom Home by RedAwning

Mountain Willow At Grand Park 4 Bedroom Home by RedAwning
3.5 star property
Fraser
The price is CA $620
CA $2,162 total
includes taxes & fees
Feb 9 - Feb 10
Mountain Willow At Grand Park 4 Bedroom Home by RedAwning
Condo, 2 Bedrooms | Interior

Hi Country Haus - 10-18... 2 Bedroom Condo by RedAwning

Hi Country Haus - 10-18... 2 Bedroom Condo by RedAwning
3.0 star property
Winter Park
The price is CA $297
CA $1,201 total
includes taxes & fees
Feb 9 - Feb 10
Hi Country Haus - 10-18... 2 Bedroom Condo by RedAwning
Condo, 2 Bedrooms | Balcony

Fraser Crossing/Founders Pointe, Condo | 2 Bedroom (Value-Rated Condo 3426)

Fraser Crossing/Founders Pointe, Condo | 2 Bedroom (Value-Rated Condo 3426)
3.0 star property
Winter Park Village
The price is CA $1,761
CA $2,572 total
includes taxes & fees
Feb 21 - Feb 22
Fraser Crossing/Founders Pointe, Condo | 2 Bedroom (Value-Rated Condo 3426)
Condo, 2 Bedrooms | Exterior

Trailhead Lodge 734 2 Bedroom Condo by RedAwning

Trailhead Lodge 734 2 Bedroom Condo by RedAwning
3.5 star property
Winter Park
The price is CA $298
CA $1,178 total
includes taxes & fees
Feb 10 - Feb 11
Trailhead Lodge 734 2 Bedroom Condo by RedAwning
Condo, 2 Bedrooms | Interior

Zephyr Mountain Lodge, Condo | 2 Bedroom (Select-Rated Condo 1615)

Zephyr Mountain Lodge, Condo | 2 Bedroom (Select-Rated Condo 1615)
3.5 star property
Winter Park Village
The price is CA $1,888
CA $2,757 total
includes taxes & fees
Feb 21 - Feb 22
Zephyr Mountain Lodge, Condo | 2 Bedroom (Select-Rated Condo 1615)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Park Hotel Reviews

Indian Peaks Resort

Indian Peaks Resort

10/10 Excellent
"We had late check in and good instructions went smoothly to get into room."
James 4-night trip
Posted 5 days ago
Indian Peaks Resort

Find out more about Winter Park

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winter Park. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we give you a choice of vacation rentals in Winter Park close to Amaze'n Maze Winter Park, or you can select a more remote option if you want a relaxing stay. Visitors like the ski slopes and majestic mountain landscape in Winter Park. You can also check out the live music while you're visiting.

What are some of the best vacation home rentals that Winter Park has to offer?

Borders Nat'l Forest at a Trailhead. 3.3 Miles to Winter Park Resort. Sleeps 12: This highly rated vacation home rental in Winter Park is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Other favorite homes for rent in Winter Park are Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus... and Creekside Luxury Retreat • 8BR • Walk to Shops, Dining & Shuttle • Sleeps 22.

How many vacation rentals are there in Winter Park?

With 357 Expedia vacation rentals, you're sure to find just the right place for your Winter Park stay.

What’s there to see and do in Winter Park?

The Fraser River Trail and Arapaho National Recreation Area are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Amaze'n Maze Winter Park. While here, Winter Park Ski Resort and Trestle Bike Park are other places worth a visit.

What’s a vacation rental in Winter Park like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winter Park. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family trip.