Vacation Rentals & Villas in Winter Park

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Ultra Luxe 7000 Sqft Winter Park Cabin

Winter Park villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 36

Match: Bicycles available Jacuzzi or hot tub

All filters match

Price per night from

$2,869

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

Match: Bicycles available Jacuzzi or hot tub

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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

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$276

Modern Comfort in the Heart of Winter Park with Resort Shuttle

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$167

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: Bicycles available Jacuzzi or hot tub

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Price per night from

$541

Alpine Chic Escape: New Ski Town Condo - Shuttle Service, Shared Hot Tub

Winter Park condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$167

NEW High-Altitude Hideaway at Lakota Townhomes

Winter Park house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$962

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$215

Ideal Location with Spacious Patio and Shared Hot Tub near Winter Park Resort

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$239

Peak Season Paradise: Ski Resort Luxury Meets Summer Relaxation

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$300

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

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$311

Downtown Winter Park | 1-Stop Shuttle to Trestle Bike Park | Hot Tub

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$94

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

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$179

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

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$480

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

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$143

Cozy Winter Park Hideaway: Pool, Hot Tub, and Resort Shuttle Nearby

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$119

Canine-Friendly Retreat: Downtown Winter Park, Shuttle to Resort

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$143

SnowBlaze Condo: Clubhouse & Mountain Views

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

Match: Bicycles available Jacuzzi or hot tub

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Price per night from

$179

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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: Jacuzzi or hot tub, Bicycles available

1 of 2 filters match

Price per night from

$311

Zephyr Mountain Lodge, Condo | 2 Bedroom (Select-Rated Condo 1315)

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$286

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: Bicycles available, Jacuzzi or hot tub

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: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$348

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: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$408

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: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$480

2bd/2bath Condo in Town of Winter Park - Ski, Bike, Music!

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$373

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$184

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

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$420

Hideaway Station TE-209

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

Base Camp 490

Winter Park condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$517

Hideaway Station Unit TS-23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$334

Hideaway Station Unit TE-405

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$221

Trailhead Lodges 211

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$186

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$172

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$172

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

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

1 of 2 match: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$574

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: Bicycles available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$277

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