Vacation Rentals & Villas in Winter Park

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61 villas

Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Grill Pets allowed

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Price per night from

$258

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Grill Pets allowed

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Price per night from

$147

Beautiful Mountain Lodge-Ski, Hike, Bike, Relax..

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

Match: Grill Pets allowed

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Price per night from

$574

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Grill Pets allowed

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Price per night from

$334

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

Match: Grill Pets allowed

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Price per night from

$540

Responds fast! avg. 2 hours 32 minutes

Match: Grill Pets allowed

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Price per night from

$179

Live Music Views from Hideaway Park Condo with Pool

Winter Park condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

Match: Grill Pets allowed

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Price per night from

$275

Trailhead Lodges 721

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Grill Pets allowed

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Price per night from

$132

Rock & Stars Chalet: Luxury with Electric Car Charger, and Private Hot Tub!

Winter Park house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 32 minutes

Match: Grill Pets allowed

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Price per night from

$419

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Riverfront Upscale remodel in great location

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Grill, Pets allowed

1 of 2 filters match

Price per night from

$304

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Grill, Pets allowed

1 of 2 filters match

Price per night from

$186

Summer Retreat: Dog-Friendly Condo Near Music Scene in Downtown Winter Park

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Grill, Pets allowed

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Price per night from

$179

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Grill, Pets allowed

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Price per night from

$215

SnowBlaze Condo: Clubhouse & Mountain Views

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Grill, Pets allowed

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Price per night from

$179

Pet-Friendly Escape: Downtown Convenience, Resort Shuttle, Clubhouse Fun

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Grill, Pets allowed

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Price per night from

$142

Winter Park Mountain Getaway!

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Grill

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Price per night from

$287

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: Pets allowed, Grill

1 of 2 filters match

Price per night from

$239

Winter Wonderland: Hot Tub Getaway in Grand Park with Heated Garage

Winter Park house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Grill

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Price per night from

$347

Alpine Hideaway: Private Hot Tub in Ideal Mountain Haus, 10-Min Shuttle to

Winter Park townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$407

Summertime Splendor: Mountainside Haven Hot Tub Oasis!

Winter Park townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$479

Fraser Crossing 3405

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$134

Trailhead Lodges 211

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$147

Fraser Crossing 3227

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$149

Base Camp 490

Winter Park condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$517

Founders Pointe 4471

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$134

Founders Pointe 4473

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$149

Timber Fox 1403

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$147

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: Pets allowed, Grill

1 of 2 filters match

Price per night from

$203

Cozy Retreat with Private Hot Tub | Spacious Winter Haven near Downtown Winter

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$275

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: Pets allowed, Grill

1 of 2 filters match

Price per night from

$479

Mountain Majesty: Panoramic Views, Hot Tub, and Easy Access to Shuttle Route!

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$311

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$172

Luxury in Downtown Winter Park CO

Winter Park townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 15 minutes

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$277

COZY CONDO ~ Ski In/ Ski Out at Winter Park Village

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$476

Luxury Mountain Haven! Family-Friendly, Ski, Bike, Hike, and Hot-Tub!

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$230

Fraser Crossing 3423

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$134

Arrow 288

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$250

Trailhead Lodges 524

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Grill

1 of 2 filters match

Price per night from

$207

Viewing 38 of 61
rentals in Winter Park

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