A1Vacations is part of HomeAway.com, the world’s leading vacation rentals marketplace.
Search over 150,000 vacation rentals properties now!   Click here to see more Vacation Homes

Search for vacation rental homes in Winter Park Area

There’s Nothing Boring about Winter Park Area Rentals

Unless you’re actually planning to move here, your visit to the Winter Park Area will make for a classic case of so much to do, so little time. Whether you and your family prefer the summer or the winter, you’ll find yourselves constantly amazed by the vastness of the landscape and the array of possibilities that each vacation moment will hold.


Loads of powdery snow that doesn’t have to be scraped or shoveled away will lend a joyful mood to the air. Brush up on your skiing skills (there are lessons for anyone who needs them) and check out the excellent conditions for snowshoeing, snowboarding, ice skating and more. If you feel like taking it easy there’s a sleigh waiting to whisk you away (yes, of course there’s hot chocolate), and the town of Winter Park has plenty of restaurants and shops to warm you up in preparation for another round of outdoor excursions.


In the summer it’s the same story, just different conditions. White water rafting, horseback riding, hiking and biking are a few typical distractions to look forward to – not that they’ll feel mundane in any way. A regular day in Winter Park, Black Hawk or Fraser actually changes the definition of “regular” and will certainly spoil you for a while.


A cabin or condo providing stunning views and plenty of space for everyone to coexist comfortably will be the finishing touch to a successful trip. Be warned, however; securing one of the Winter Park vacation rentals waiting alluringly on the mountainside will only make it harder to go back to the real world.


Not that that should stop you from visiting one of Colorado’s most approachable destinations for families (or any group, really)…and you can always come back again soon.

  • Next Page
Go to page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. 7
  8. 8
  9. 9
  10. 10
(1 - 10 of 247)

  1. 'Base Camp' in Winter Park, 2BR Condo Accesses All Activities Year-Round — Property 139893

    Vacation Condo rental in Winter Park Area area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • mountain, town
    • sauna
    It's Snowing!!! Book in Nov to Save 20%
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $450 - $1650 per property per week

  2. Founders Pointe Luxury Condo
    New Ski-In/Out Luxury Condo In Resort Base Village With Amazing Views — Property 200486

    Vacation Condo rental in Winter Park Area area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • mountain, resort
    • garden
    Save 25% And The Cleaning Fee Is Waived
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1043 - $2193 per property per week

  3. Winter Park Condo Great Views, Pool, Hot Tubs, Tennis, Great Rates — Property 100343

    Vacation Condo rental in Fraser area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • mountain, resort
    • pool
    Book Now and Save $$$
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $480 - $1275 per property per week

  4. Iron Horse 5094
    Ski-in/Ski-Out, 5-Star, Best Location in Iron Horse, 2 BR/2 BA, Sleeps 8, pool — Property 254185

    Vacation Condo rental in Winter Park area
    • Condo
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • mountain, resort
    • pool
    Rates (shown in USD)
    $595 - $3465 per property per week

  5. Gorgeous New Mountain Home, Private Hot Tub, Huge Kitchen, Heated Garage in the — Property 319187

    Vacation House rental in Winter Park area
    • House
    • 3 bedrooms , sleeps 10
    • 2 bathrooms
    • 1 half bathroom
    • mountain, resort
    • satellite or cable
    Rates (shown in USD)
    $1400 - $3850 per property per week

  6. Convenient Downtown Studio with All the Amenities — Property 319288

    Vacation Studio rental in Winter Park area
    • Studio
    • studio , sleeps 4
    • 1 bathroom
    • downtown, mountain
    • pool
    Rates (shown in USD)
    $385 - $805 per property per week

  7. Call For Special Deals, Walking Distance to Ski Area — Property 201430

    Vacation Condo rental in Winter Park area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • mountain, rural
    • internet access
    Rates (shown in USD)

  8. Beautiful Townhome - Private Hot Tub - Free High Speed Internet! — Property 144528

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • 1 half bathroom
    • mountain, town
    • balcony
    Rates (shown in USD)
    $1050 - $3780 per property per week

  9. State-of-the-Art, 5 Bedroom Home — Property 188626

    Vacation House rental in Winter Park area
    • House
    • 5 bedrooms , sleeps 12
    • 3 bathrooms
    • 1 half bathroom
    • mountain, resort
    • jacuzzi
    Rates (shown in USD)
    $2250 - $5500 per property per week

  10. Downtown Winter Park Townhome
    3 Bedroom Downtown Winter Park Townhome w/ HOT TUB — Property 200095

    Vacation Townhome rental in Winter Park area
    • Townhome
    • 3 bedrooms , sleeps 7
    • 3 bathrooms
    • 1 half bathroom
    • mountain, resort
    • tennis court
    Rates (shown in USD)
    $875 - $3750 per property per week

Refine Your Search

You refined by:
Winter Park Area remove
(remove all)
Find by availability dates:

Regions

Bedrooms

Sleeps

Baths

Lodging Type

Amenities

Leisure Activities

Suitability

Other

  • Next Page
Go to page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. 7
  8. 8
  9. 9
  10. 10
(1 - 10 of 247)