Spacious cabin rentals and modern condo vacation rentals in Winter Park put you near all the action on the ski resort's mountainside. Enjoy the woodsy locale and proximity to Colorado's scenic nature.

Choose the perfect vacation rental
Best Vacation Home Deals in Winter Park
Compare and find a vacation rental that fits your needs among the 3,410 fantastic rentals from several partner websites in Winter Park. Every one of the offers from our partner websites are instantaneously compared on our website , allowing you to save up to 56%.
Top-Rated Rentals and Accommodations in Winter Park
Recommended Vacation Rentals in Winter Park
Find your perfect vacation rental in Winter Park: from $100 per night
Budget-friendly Vacation Rentals in Winter Park
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Winter Park accommodation with high-speed internet.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Winter Park rental with full kitchen.
Apartments With Balconies or Patios
Looking for a home with a balcony? Check out these vacation homes in Winter Park with their own private patios and balconies.
Popular Rental Amenities in Winter Park
Price and Availability Index in Winter Park
Vacation Rental Price Information in Winter Park
The graph shows the average rental prices for the next twelve months in Winter Park. It is during a week of December (12/23 - 12/30) that you will find the highest prices for the next 12 months. Prices decrease in a week of May (5/6 - 5/13), where average prices are $299.
Rental Availability Information in Winter Park
Our availability graph helps you identify the busiest months in Winter Park. The most challenging week to find a rental in the next twelve months is in December (12/30 - 1/6). Conversely, you will find the highest percentage of available offers in Winter Park in October (10/28 - 11/4).
The Weather in Winter Park
This is the climate diagram in Winter Park. During July, maximum temperatures go up to more than 54° On the other hand, you could have temperatures dropping under 5° in December. The rainiest month is May while the driest month is March.
7-Day Weather Forecast in Winter Park
Accommodations for your vacation in Winter Park
Information about vacation rentals in Winter Park
🏡 Vacation rentals | 3,410 properties |
---|---|
💳 Possible discounts | up to 56% |
🌙 Nightly prices starting at | $95 |
⭐ Popular amenities | Internet, Kitchen and Microwave |
🐾 Pet friendly accommodations | 592 properties |
🏊 Vacation rentals with pools | 2,392 properties |
Frequently Asked Questions
What is the typical nightly price for a vacation rental in Winter Park?
The price of a night's stay in Winter Park starts at $95. If you are looking for a house rental, the nightly price is $713 on average. A apartment rental Winter Park will cost $409 per night on average.
How many vacation homes are available to book in Winter Park?
There are 3,410 vacation rentals available for booking for your upcoming trip.
What are the most popular amenities for vacation rentals in Winter Park?
Three most popular amenities for vacation rentals in Winter Park include accommodations that have: Internet, Kitchen, and Microwave.
Are pets allowed in vacation homes in Winter Park?
Finding a vacation home in Winter Park that allows pets is definitely possible, with 592 pet-friendly available.
What's the best time of year to travel to Winter Park?
Winter Park has its warmest time of year around July and June, with average nightly prices around $95.
We list offers from thousands of providers, including:











Vacation Destinations Near Winter Park
-
Fraser Vacation Rentals
-
Tabernash Vacation Rentals
-
Georgetown Vacation Rentals
-
Granby Apartments
-
Black Hawk Vacation Rentals
-
Idaho Springs Vacation Rentals
-
Vacation Rentals in Keystone
-
Silverthorne Vacation Rentals
-
Dillon Vacation Rentals
-
Allenspark Vacation Rentals
-
Cabins in Grand Lake
-
Wildernest Vacation Rentals
-
Vacation Rentals in Frisco
-
Evergreen Vacation Rentals
-
Vacation Rentals in Boulder
-
Vacation Rentals in Breckenridge
-
Idledale Vacation Rentals
-
Golden Vacation Rentals
-
Arvada Vacation Rentals
-
Copper Mountain Vacation Rentals
Top Vacation Ideas
- Miami Spring Break Hotels & Vacation Rentals
- South Padre Island Spring Break Hotels & Vacation Rentals
- Lake Havasu Spring Break Hotels & Vacation Rentals
- Texas Spring Break Vacation
- Miami Beach Spring Break Hotels & Vacation Rentals
- Romantic Getaways in Florida
- California Spring Break Vacation
- Bora Bora Honeymoon
- Romantic Getaways in Ohio
- Myrtle Beach Spring Break Hotels & Vacation Rentals
- Road Trips in Texas
Explore More Vacation Ideas
-
Pet Friendly Rentals in South Padre Island
-
Summer Vacations in Alaska
-
Massachusetts Music Venues
-
Road Trips in Wyoming
-
Chicago Hotels & Vacation Rentals for the 4th of July
-
Honeymoon on Santa Catalina Island
-
Pet Friendly Rentals in Helen
-
Pittsburg, NH Cabin Rentals
-
Pet Friendly Rentals in Idaho
-
Tennessee Thanksgiving Getaway
-
Hotels in Wisconsin Dells
-
Hotels in Galveston
-
December Travel in North Carolina
-
Girls Trip in Miami
-
Road Trips in Washington State
-
San Diego Hotels & Vacation Rentals for New Year's Eve
-
Traverse City Cabin Rentals
-
March Vacations on the East Coast
-
Summer Vacations in York
-
Romantic Getaways in Arizona
-
City Breaks in Gatlinburg