Vacation Rentals & Villas in Winter Park

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88 villas

Escape to Grand Lake: Luxury Cabin with Unmatched Views and Entertainment

Grand Lake house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 32 minutes

Match: Jacuzzi or hot tub Sea view

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Price per night from

$419

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Rendezvous Retreat

Fraser villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,229

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$455

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$286

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$373

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: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$179

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: Sea view, 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: Sea view, Jacuzzi or hot tub

1 of 2 filters match

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: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$407

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$335

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$184

2185 Pioneer Trail

Fraser house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$259

Hideaway Station Unit TE-405

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$221

Hideaway Station Unit TS-23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

219 Elk Ranch Road

Fraser house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$401

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$334

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$186

Blue Bear Chalet

Fraser house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$250

Hideaway Station TE-209

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

Hidden River Ranch

Tabernash house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$687

Elk Creek Condos B102

Fraser condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$192

The Highlander

Fraser house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 11

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$250

Trailhead Lodges 211

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

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

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$94

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: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$203

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: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$287

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: Sea view, Jacuzzi or hot tub

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: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$479

Mountain Bliss Retreat: Spectacular Views & Modern Comforts

Grand Lake cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$347

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

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$166

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

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$166

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: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$311

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: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$419

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: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$179

Sky House: Summit Retreat with Breathtaking Panoramic Views and Hot Tub

Tabernash house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$492

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$172

Great Views & Rates - Winter Park Area - Colorado

Fraser apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great value, comfortable accomodations, and great owner” The owner is responsive, prompt, and courteous. We've used this condo every year for the past 11 years, and until recently, I had never even spoken to the owner- all email and all arrangements flawlessly executed, every time. Accomodations are comfortable and casual. Best feature is that this condo is directly next to the clubhouse and ski shuttle stop- very convenient! We love staying here.

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$132

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

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$574

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