Vacation Rentals & Villas in Winter Park

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66 villas

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

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Jacuzzi or hot tub Pets allowed

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Price per night from

$258

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Jacuzzi or hot tub 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: Jacuzzi or hot tub Pets allowed

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Price per night from

$573

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: Jacuzzi or hot tub Pets allowed

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Price per night from

$540

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Jacuzzi or hot tub Pets allowed

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Price per night from

$186

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Jacuzzi or hot tub Pets allowed

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Price per night from

$215

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Jacuzzi or hot tub Pets allowed

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Price per night from

$334

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: Jacuzzi or hot tub 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

Match: Jacuzzi or hot tub Pets allowed

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Price per night from

$142

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: Jacuzzi or hot tub Pets allowed

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Price per night from

$275

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: Jacuzzi or hot tub Pets allowed

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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

Match: Jacuzzi or hot tub Pets allowed

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Price per night from

$179

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, 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: Pets allowed, 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: Pets allowed, 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: Pets allowed, Jacuzzi or hot tub

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, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$479

Trailhead Lodges 721

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Pets allowed

1 of 2 filters match

Price per night from

$132

Hideaway Station Unit TE-405

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$221

Hideaway Station TE-209

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, 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: Pets allowed, 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: Pets allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$517

Trailhead Lodges 211

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$147

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, 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: Pets allowed, 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: Pets allowed, Jacuzzi or hot tub

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, 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: Pets allowed, 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: Pets allowed, 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: Pets allowed, 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: Pets allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$311

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Jacuzzi or hot tub, Pets allowed

1 of 2 filters match

Price per night from

$179

Riverfront Upscale remodel in great location

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Pets allowed

1 of 2 filters match

Price per night from

$304

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$172

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Jacuzzi or hot tub

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, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$276

Trailhead Lodges 212

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$132

Trailhead Lodges 232

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pets allowed, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$132

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