Vacation Rentals & Villas in Winter Park

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58 villas

Trailhead Lodges 524

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

All filters match

Price per night from

$207

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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

All filters match

Price per night from

$148

Trailhead Lodges 212

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

All filters match

Price per night from

$133

Trailhead Lodges 232

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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

All filters match

Price per night from

$133

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

1 of 2 filters match

Price per night from

$156

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

1 of 2 filters match

Price per night from

$240

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

1 of 2 filters match

Price per night from

$349

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

1 of 2 filters match

Price per night from

$409

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

1 of 2 filters match

Price per night from

$481

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$374

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$95

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

1 of 2 filters match

Price per night from

$204

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

1 of 2 filters match

Price per night from

$542

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

1 of 2 filters match

Price per night from

$276

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

1 of 2 filters match

Price per night from

$481

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

1 of 2 filters match

Price per night from

$167

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

1 of 2 filters match

Price per night from

$167

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

1 of 2 filters match

Price per night from

$312

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

1 of 2 filters match

Price per night from

$421

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

1 of 2 filters match

Price per night from

$180

Base Camp 490

Winter Park condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

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

1 of 2 filters match

Price per night from

$519

Hideaway Station Unit TS-23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$148

Hideaway Station TE-209

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$148

The Condo at The Gondo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$180

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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

1 of 2 filters match

Price per night from

$335

Trailhead Lodges 211

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$148

Hideaway Station Unit TE-405

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$222

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$187

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$173

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$173

Luxury in Downtown Winter Park CO

Winter Park townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

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

1 of 2 filters match

Price per night from

$277

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

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

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

1 of 2 filters match

Price per night from

$575

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

1 of 2 filters match

Price per night from

$259

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

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$478

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

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$230

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

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

1 of 2 filters match

Price per night from

$156

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

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

1 of 2 filters match

Price per night from

$288

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