Winter Park: Vacation Rental By Owner

Showing 20 Of 611 Vacation Rentals
  • Property-1 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (11) Wonderful
    Winter Park, CO

    Beaver Village 16-31 - a SkyRun Winter Park Property IMPORTANT NOTICE: Due to Grand County Public Health order the rental of properties for less then 30 days is... ...more

  • Property-2 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (4) Good
    Winter Park, CO

    Founders Pointe 4368 - a SkyRun Winter Park Property IMPORTANT NOTICE: Due to Grand County Public Health order the rental of properties for less then 30 days is... ...more

  • Property-3 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (67) Wonderful
    Winter Park, CO

    As part of my COVID response, my cleaner is following the CDC guidelines for cleaning. I am providing Bleach Solution, Wipes, Masks, Touchless Thermometer, and... ...more

  • Property-4 Image 1
    Cabin Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (59) Excellent
    Winter Park, CO

    For your next alpine retreat, escape to this 2-bed, 2-bath Winter Park vacation rental cabin for the ultimate Rocky Mountain experience. Offering all the... ...more

  • Property-5 Image 1
    Condo Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (27) Excellent
    Winter Park, CO

    Fall in love with the Rocky Mountains from this newly built 4-bedroom, 3-bathroom Winter Park vacation rental condo that sleeps 12! Walk down to Main Street to... ...more

  • Property-6 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (30) Very Good
    Winter Park, CO

    Whether you're looking for a relaxing alpine getaway or a vacation full of thrilling adventures on snow-capped peaks, there's no better destination for a mountain... ...more

  • Property-7 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (85)
    Winter Park, CO

    ZEPHYR! PREMIER TRUE SKI-IN SKI-OUT 2 BR/ 2 BA CONDO ON A HIGH FLOOR (Slopeside) OVERLOOKING THE SLOPES (Lower Hughes, Brian's Way and Corona Way w gondola)... ...more

  • Property-8 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (21) Wonderful
    Winter Park, CO

    LOCATION, LOCATION, LOCATION Steps from Winter Park restaurants, shops, Fraser River Trail and free bus route. Completely updated spacious 2-bedroom, 1.5-bath... ...more

  • Property-9 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    Winter Park, CO

    IN ORDER TO HELP MITIGATE THE SPREAD OF COVID-19 AND IN COMPLIANCE WITH THE STATE OF COLORADO and GRAND COUNTY PUBLIC HEALTH ORDERS, PLEASE BE AWARE THAT THIS... ...more

  • Property-10 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (13)
    Winter Park, CO

    IN ORDER TO HELP MITIGATE THE SPREAD OF COVID-19 AND IN COMPLIANCE WITH THE STATE OF COLORADO and GRAND COUNTY PUBLIC HEALTH ORDERS, PLEASE BE AWARE THAT THIS... ...more

  • Property-11 Image 1
    Townhome Select Dates for Price
    • 3 Bed
    • 4 Baths
    • (6) Excellent
    Winter Park, CO

    IN ORDER TO HELP MITIGATE THE SPREAD OF COVID-19 AND IN COMPLIANCE WITH THE STATE OF COLORADO and GRAND COUNTY PUBLIC HEALTH ORDERS, PLEASE BE AWARE THAT THIS... ...more

  • Property-12 Image 1
    Townhome Select Dates for Price
    • 3 Bed
    • 4 Baths
    • (7)
    Winter Park, CO

    IN ORDER TO HELP MITIGATE THE SPREAD OF COVID-19 AND IN COMPLIANCE WITH THE STATE OF COLORADO and GRAND COUNTY PUBLIC HEALTH ORDERS, PLEASE BE AWARE THAT THIS... ...more

  • Property-13 Image 1
    Condo Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (70) Excellent
    Winter Park, CO

    REC CENTER INCLUDING POOL AND HOT TUBS CLOSED UNTIL FURTHER NOTICE. The perfect getaway...Remodeled, beautifully decorated Condo right in the town of Winter Park.... ...more

  • Property-14 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (70) Excellent
    Winter Park, CO

    Amazing views / Large Hot Tub / Heated Garage / 2 minute Walk to the Slopes. This 1 bedroom / 1 bathroom unit is a newer private top-floor unit with great... ...more

  • Property-15 Image 1
    Condo Select Dates for Price
    • 3 Bed
    • 3 Baths
    • (40) Exceptional
    Winter Park, CO

    *Please note, we have switched to a more generous cancellation policy. Additionally, if there is a stay at home order in Colorado or your home state, we will... ...more

  • Property-16 Image 1
    Townhome $342 / Nightly
    • 3 Bed
    • 4 Baths
    • (11) Wonderful
    Winter Park, CO

    * TurnKey photo-verifies this home is professionally cleaned with products approved by the EPA for use against COVID-19. Bookings at this home include a 24-hr... ...more

  • Property-17 Image 1
    Townhome Select Dates for Price
    • 3 Bed
    • 3 Baths
    • (1) Exceptional
    Winter Park, CO

    Inside you'll discover three bedrooms, three bathrooms, an open plan for the living room and kitchen, laundry room and a private deck overlooking the open space... ...more

  • Property-18 Image 1
    Condo Select Dates for Price
    • 1 Baths
    • (50)
    Winter Park, CO

    Amazing views / Large Hot Tub / Heated Garage / 2 minute Walk to the Slopes. This studio unit is a newer private top floor unit with great views of the slopes... ...more

  • Property-19 Image 1
    Chalet Select Dates for Price
    • 3 Bed
    • 4 Baths
    • (9) Excellent
    Winter Park, CO

    CURRENT SPECIAL & POLICY UPDATE - For a limited time only we are offering discounts of up to 50% off which are already included in the quoted nightly rates. We... ...more

  • Property-20 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (37) Wonderful
    Winter Park, CO

    CURRENT SPECIAL & POLICY UPDATE - For a limited time only we are offering discounts of up to 50% off which are already included in the quoted nightly rates. We... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Winter Park. Many accommodations in Winter Park provide "Non Smoking Only", there are 137, or there are 129 of Vacation Rentals in Winter Park with a "Children Welcome", there are also 126 with "Skiing", which is another great reason to visit Winter Park.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Winter Park. The most expensive month of the next 12 months is in July, where prices hit an average of $41 a night. In June, prices will hit an average low of $70 per night.