Vacation Rentals & Villas in Winter Park

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66 villas

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Jacuzzi or hot tub

All filters match

Price per night from

$172

Responds fast! avg. 2 hours 32 minutes

Match: Shared outdoor pool (heated) Jacuzzi or hot tub

All filters match

Price per night from

$190

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: Shared outdoor pool (heated) Jacuzzi or hot tub

All filters match

Price per night from

$239

Hideaway Park Gem: Ski Shuttle, Pool, and Mountain Views

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

Match: Shared outdoor pool (heated) Jacuzzi or hot tub

All filters match

Price per night from

$142

Tranquil Ski Haven: Slope-Side Retreat, Ski In/Ski Out Access

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 32 minutes

Match: Shared outdoor pool (heated) Jacuzzi or hot tub

All filters match

Price per night from

$155

Relaxed Slope-Side Living: Ski In/Ski Out Bliss in Cool Winter Park

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

Match: Shared outdoor pool (heated) Jacuzzi or hot tub

All filters match

Price per night from

$190

Responds fast! avg. 2 hours 32 minutes

Match: Shared outdoor pool (heated) Jacuzzi or hot tub

All filters match

Price per night from

$155

Responds fast! avg. 2 hours 32 minutes

Match: Shared outdoor pool (heated) Jacuzzi or hot tub

All filters match

Price per night from

$215

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: Shared outdoor pool (heated) Jacuzzi or hot tub

All filters match

Price per night from

$118

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$372

Modern Mountain Oasis: Downtown Winter Park Retreat with Pool & Hot Tub

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$155

Powder and Pines: Slope-Seeker's Old Town Woodland Retreat

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$407

Slope-Side Luxury: Private Hot Tub at Winter Park Resort

Winter Park townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$479

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$184

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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), Jacuzzi or hot tub

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: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$540

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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$479

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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$179

Base Camp 490

Winter Park condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$517

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$186

Hideaway Station Unit TE-405

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$221

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$334

The Condo at The Gondo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$179

Hideaway Station TE-209

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

Hideaway Station Unit TS-23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

Trailhead Lodges 211

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$172

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

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$258

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

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$476

Luxury in Downtown Winter Park CO

Winter Park townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Shared outdoor pool (heated), Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$276

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rentals in Winter Park

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