Vacation Rentals & Villas in Winter Park

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105 villas

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

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$258

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Clothes dryer Jacuzzi or hot tub

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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

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$2,867

Trailhead Lodges 524

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$207

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$147

Trailhead Lodges 212

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$132

Hideaway Station Unit TE-405

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$222

Hideaway Station Unit TS-23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$147

Arrow 288

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$250

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$172

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

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$574

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: Clothes dryer Jacuzzi or hot tub

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Price per night from

$263

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: Clothes dryer 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: Clothes dryer Jacuzzi or hot tub

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Price per night from

$276

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: Clothes dryer Jacuzzi or hot tub

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Price per night from

$540

Majestic Moose Haven: Rustic Retreat with Hot Tub in the Mountains

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$287

Cool Condo with Trestle Bike Park Access

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$359

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: Clothes dryer Jacuzzi or hot tub

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Price per night from

$167

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

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Clothes dryer Jacuzzi or hot tub

All filters match

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

Match: Clothes dryer Jacuzzi or hot tub

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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

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$407

NEW High-Altitude Hideaway at Lakota Townhomes

Winter Park house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$961

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: Clothes dryer Jacuzzi or hot tub

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Price per night from

$143

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$334

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: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$311

Base Camp 490

Winter Park condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$517

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: Clothes dryer Jacuzzi or hot tub

All filters match

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: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$118

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: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$167

Trailhead Lodges 211

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$147

Quiet Winter Park Townhome | Private Hot Tub | Close to Mountain Biking

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 32 minutes

Match: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$359

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

Match: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$311

Luxury in Downtown Winter Park CO

Winter Park townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 15 minutes

Match: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$277

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$186

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: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$480

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: Clothes dryer Jacuzzi or hot tub

All filters match

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: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$300

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Jacuzzi or hot tub

All filters match

Price per night from

$374

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