Vacation Rentals & Villas in Winter Park

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Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Swimming pool

All filters match

Price per night from

$172

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Riverfront Upscale remodel in great location

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$304

Cozy 2 bed 2 bath Winter Park Mountain Cabin

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$144

NEW! IFIRESIDE MOOSE CONDO - WALK TO TOWN, FRONT DOOR SKI SHUTTLE PICK-UP

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$281

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: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$179

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: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$94

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: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$179

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Swimming pool

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: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$277

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$147

Trailhead Lodges 212

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Swimming pool

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: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$132

Trailhead Lodges 524

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$207

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: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$119

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: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$239

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

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$276

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: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$143

Tranquil Ski Haven: Slope-Side Retreat, Ski In/Ski Out Access

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$155

Relaxed Slope-Side Living: Ski In/Ski Out Bliss in Cool Winter Park

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$191

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$155

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$191

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$215

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

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$143

Canine-Friendly Retreat: Downtown Winter Park, Shuttle to Resort

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$143

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