Vacation Rentals & Villas in Winter Park

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126 villas

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

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$259

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$184

Ultra Luxe 7000 Sqft Winter Park Cabin

Winter Park villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 36

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Price per night from

$2,869

Trailhead Lodges 524

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$207

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$147

Trailhead Lodges 212

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$132

Hideaway Station Unit TS-23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$147

Arrow 288

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$250

Fraser Crossing 3405

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$134

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

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

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Price per night from

$574

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: Fireplace

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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

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Price per night from

$275

Downtown Wooded Mountain Setting! Next to Wolf Park on FREE Shuttle. Tim

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$227

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

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$230

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

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Price per night from

$347

Quick & Easy Access to the Gondola at Winter Park Resort

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$155

NEW High-Altitude Hideaway at Lakota Townhomes

Winter Park house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$960

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: Fireplace

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Price per night from

$142

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

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Price per night from

$311

Base Camp 490

Winter Park condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

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Price per night from

$517

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: Fireplace

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Price per night from

$166

Rustic Charm and Urban Comforts: Winter Park Cabin with Hot Tub and Wildlife

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$275

Zephyr Mountain Lodge Slopeside 1420

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$209

Luxury in Downtown Winter Park CO

Winter Park townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$276

Timber Fox 1403

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$147

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

Match: Fireplace

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Price per night from

$479

Riverside Sanctuary: Old Town Winter Park

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$239

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$190

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: Fireplace

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Price per night from

$299

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Fireplace

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Price per night from

$373

Hideaway Station TE-209

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Match: Fireplace

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Price per night from

$147

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$179

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

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$477

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$155

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

Match: Fireplace

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Price per night from

$419

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Fireplace

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Price per night from

$286

Ski & Mountain Views with Hot Tub at Rendezvous

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Fireplace

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Price per night from

$263

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: Fireplace

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Price per night from

$540

Viewing 38 of 126
rentals in Winter Park

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