Vacation Rentals & Villas in Winter Park

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

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace Pets allowed

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Price per night from

$258

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

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

Match: Balcony or terrace Pets allowed

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Price per night from

$574

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Balcony or terrace Pets allowed

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Price per night from

$215

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: Balcony or terrace Pets allowed

All filters match

Price per night from

$540

Responds fast! avg. 2 hours 32 minutes

Match: Balcony or terrace Pets allowed

All filters match

Price per night from

$179

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: Balcony or terrace Pets allowed

All filters match

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: Balcony or terrace Pets allowed

All filters match

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: Balcony or terrace Pets allowed

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Price per night from

$275

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: Balcony or terrace Pets allowed

All 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

Match: Balcony or terrace Pets allowed

All filters match

Price per night from

$179

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Trailhead Lodges 721

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Balcony or terrace, Pets allowed

1 of 2 filters match

Price per night from

$132

Riverfront Upscale remodel in great location

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Balcony or terrace, Pets allowed

1 of 2 filters match

Price per night from

$304

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Balcony or terrace, Pets allowed

1 of 2 filters match

Price per night from

$334

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Balcony or terrace, Pets allowed

1 of 2 filters match

Price per night from

$186

Cozy Condo in Downtown Winter Park | Rec Center + Hot Tub

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$142

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Balcony or terrace, Pets allowed

1 of 2 filters match

Price per night from

$147

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, Balcony or terrace

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, Balcony or terrace

1 of 2 filters match

Price per night from

$239

Alpine Charm in Downtown Winter Park - Views Included, Steps to Everything

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$311

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: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$479

Snowblaze A23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$117

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

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$227

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, Balcony or terrace

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, Balcony or terrace

1 of 2 filters match

Price per night from

$275

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, Balcony or terrace

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, Balcony or terrace

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, Balcony or terrace

1 of 2 filters match

Price per night from

$311

Hideaway Station Unit TE-405

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$221

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, Balcony or terrace

1 of 2 filters match

Price per night from

$276

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

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$299

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

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$229

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: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$155

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: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$287

Ski & Mountain Views with Hot Tub at Rendezvous

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$263

Ski Ready: Downtown Winter Park, Resort Shuttle at Your Doorstep

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$227

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

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$118

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

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 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

1 of 2 match: Pets allowed, Balcony or terrace

1 of 2 filters match

Price per night from

$142

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