Search for vacation rental homes in Winter Park

Winter Park Welcomes You (and Your Entire Group)

Crisp air, bright snow and free reign to leave your worries at home are just a few of the things that a trip to Winter Park will bring to the table. Pack up, bundle up and make your way to the Rocky Mountains and you’ll soon be feeling the delightful rush of vacation success.


Bringing the family to a place like Winter Park Colorado is a pretty safe bet. Mesmerizing scenery made accessible by chair lifts, mountaintop restaurants, snowcats and guided snowshoe tours will include everyone in the fun, so bring along whoever you please.


Kids can take lessons to learn the basics while the more experience skiers head out to reclaim their ski legs, and the more subdued among you can simply ride to the Sunspot Lodge, hang out in the village or find a place by the fire and watch the happy people come and go.


Diverse traveling groups are best accommodated in lodgings that allow for plenty of space, privacy and comfort. Sound like a tall order? Winter Park Vacation Rentals meet the task at hand; each condo, chalet and cabin creates a home-like atmosphere without demanding too much in return. Groups fit well into these lodging situations, so even if you have quite the colorful crew on your hands you shouldn’t worry about going without important amenities or the secure sense that everyone is having a good time.


Breathe easily as you prepare to gather everyone into a manageable herd and show them a good time here in the Winter Park Area. Looking forward to a vacation without hesitation is something to strive for, and this time around, it’s something well within reach.

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  1. New Luxury Ski-in/Ski-Out Condo in Resort Village-Amazing Views — Property 200486

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • mountain, resort
    • accept credit card
    20% Off For Weekly Rentals
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1115 - $2240 per property per week

  2. Pristine Condo on the River with All the Modern Amenities — Property 150407

    Vacation Condo rental in Winter Park area
    • Condo
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • river
    • accept credit card
    Rates (shown in USD)

  3. Backs to National Forest and Two Minutes From Downtown — Property 150479

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 half bathroom
    • washing machine
    • internet access
    Rates (shown in USD)
    $570 - $1320 per property per week

  4. In Town Family Condo, Pool, Hot Tubs, Wi-Fi, Views — Property 160192

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • mountain, resort
    • accept credit card
    Rates (shown in USD)
    $595 - $2170 per property per week

  5. Round House - Luxury Custom home with Views, 5 Miles to Winter Park — Property 159894

    Vacation House rental in Winter Park area
    • House
    • 5 bedrooms , sleeps 18
    • 3 bathrooms
    • mountain, resort
    • washing machine
    Rates (shown in USD)
    $2400 - $5150 per property per week

  6. Winter Park Condo- Discount Rates-FREE High Speed Wireless Internet — Property 158648

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • downtown, mountain
    • swimming pool
    Rates (shown in USD)
    $725 per property per week

  7. 4 Bd/3.5 BA Luxury Townhome-Walk to Base-Spectacular Mtn. View — Property 192927

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 4 bedrooms , sleeps 13
    • 3 bathrooms
    • 1 half bathroom
    • mountain, town
    • accept credit card
    Rates (shown in USD)
    $1575 - $5250 per property per week

  8. Spacious Duplex in Winter Park — Property 188119

    Vacation House rental in Winter Park area
    • House
    • 3 bedrooms , sleeps 9
    • 2 bathrooms
    • 1 half bathroom
    • mountain, resort
    • accept credit card
    Rates (shown in USD)
    $1225 - $3150 per property per week

  9. Beautiful, Spacious Condo at Meadowridge 15-3 — Property 100192

    Vacation Condo rental in Winter Park area
    • Condo
    • 3 bedrooms , sleeps 9
    • 3 bathrooms
    • mountain, resort
    • swimming pool
    Rates (shown in USD)

  10. Free gas card, new beds, new hot tub, low rates! — Property 119194

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 9
    • 2 bathrooms
    • 1 half bathroom
    • lake, mountain
    • accept credit card
    Rates (shown in USD)

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