Vacation Rentals & Villas in Winter Park

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176 villas

Alpine Villa Retreat Breckenridge

Breckenridge villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 26

Match: Climbing frame Golf course on site or within 15 min walk

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Price per night from

$4,008

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103 Eagle Ridge Rd B-1

Granby house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$313

Alpine Charm in Downtown Winter Park - Views Included, Steps to Everything

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$311

Cozy Condo in Downtown Winter Park | Rec Center + Hot Tub

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$122

Frosty Mountain Escape in Keystone

Keystone condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$224

Highland Greens Lodge 210

Breckenridge apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

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Price per night from

$106

Riverside Sanctuary: Old Town Winter Park

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$239

Slope-Side Thrills: Bike, Hike, and Stay

Granby condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$118

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

On Shuttle Route to Slopes/Pool and Hot Tub Access/Private Deck

Keystone condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$144

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$259

Highland Greens Lodge 305

Breckenridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$121

Highland Greens Spruce

Breckenridge townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$226

Updated Condo/Private Patio/Central Location

Dillon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 55 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$129

Swans Nest Villa 1601

Breckenridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$121

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$147

Cozy Fraser Retreat: Family Space, Private Hot Tub, Convenient Shuttle

Fraser house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

Exceptional Mountain and Lake Views! 303D

Dillon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$172

Large Townhome, Exceptional Views, Hot Tub, Pool, Private Garage 97A

Wildernest condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$234

Vintage Ski Condo in Quiet Setting. Wood Fireplace, Hot Tubs, Pool. BB103

Wildernest condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$122

Ski-in/Ski-out Bliss: Your Dream Getaway near Gondola at Winter Park Resort

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$203

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$172

Cozy Oasis Near Winter Park Resort | Fraser Valley Views

Fraser condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$203

Mountain Opulence: Townhome with Private Hot Tub, Overlooking Winter Park Resort

Winter Park townhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$540

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$227

Summer Retreat in Winter Park: Your Hot Tub Hideaway

Fraser condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$287

Tranquil Retreat: 'Bear Cabin' near Rocky Mountain National Park

Grand Lake cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$299

Mountain Haven: Fraser's Paradise Escape with Pool & Hot Tub Amenitie

Fraser townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$335

Alpine Chic in the Heart of Winter Park - Hot Tub Comfort in a Modern Luxury

Winter Park townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$479

Snowy Mountain Sanctuary: Your Cozy Secluded Winter Escape

Grand Lake cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$275

Private Hot Tub, Beautiful Views, 208 Tenderfoot

Dillon house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$493

Rock & Stars Chalet: Luxury with Electric Car Charger, Ski Locker, and Private

Winter Park house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$419

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$335

Ski-in, Ski-out Bliss at Granby Ranch Resort - Brand New!

Granby townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$239

Cool Condo with Trestle Bike Park Access

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$383

Condo On Keystone Lake/Pool and Hot Tub Access

Keystone condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$172

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