Vacation Rentals & Villas in Winter Park

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29 villas

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Riverfront Upscale remodel in great location

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Swimming pool

All filters match

Price per night from

$304

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Swimming pool

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Price per night from

$172

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Swimming pool

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Price per night from

$172

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

Match: Shared indoor pool Swimming pool

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Price per night from

$190

Cozy 2 bed 2 bath Winter Park Mountain Cabin

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared indoor pool Swimming pool

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Price per night from

$143

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared indoor pool Swimming pool

All filters match

Price per night from

$280

Responds fast! avg. 2 hours 32 minutes

Match: Shared indoor pool Swimming pool

All filters match

Price per night from

$190

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Shared indoor pool Swimming pool

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Price per night from

$215

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

Match: Shared indoor pool Swimming pool

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Price per night from

$155

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

Match: Shared indoor pool Swimming pool

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Price per night from

$94

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: Shared indoor pool Swimming pool

All filters match

Price per night from

$179

Responds fast! avg. 2 hours 32 minutes

Match: Shared indoor pool Swimming pool

All filters match

Price per night from

$155

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: Shared indoor pool Swimming pool

All filters match

Price per night from

$142

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: Shared indoor pool Swimming pool

All filters match

Price per night from

$118

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

Match: Shared indoor pool Swimming pool

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Price per night from

$142

SnowBlaze Condo: Clubhouse & Mountain Views

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

Match: Shared indoor pool Swimming pool

All filters match

Price per night from

$179

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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: Shared indoor pool, Swimming pool

1 of 2 filters match

Price per night from

$276

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: Shared indoor 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: Shared indoor pool, Swimming pool

1 of 2 filters match

Price per night from

$275

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: Shared indoor pool, Swimming pool

1 of 2 filters match

Price per night from

$142

Trailhead Lodges 524

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Swimming pool

1 of 2 filters match

Price per night from

$206

Trailhead Lodges 212

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor 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: Shared indoor pool, Swimming pool

1 of 2 filters match

Price per night from

$132

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Shared indoor pool, Swimming pool

1 of 2 filters match

Price per night from

$147

Great rentals within 20 miles that match your search

Responds fast! avg. 11 minutes

Match: Shared indoor pool Swimming pool

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Price per night from

$201

“relaxing time in the mountains” This is a great place to stay near Grand lake, rocky mountain national PK and winter park, clean, safe, hot tub, pool, restaurant with sports bar on site . good places to eat within 5 min drive or walk across street to grocery store Mc D, subway, this studio can be rented alone or with an additional adjoining room with king size bed and separate bath room for an additional cost of course. We have stayed here before and will again. The studio has a pull down bed, from the wall, and sofa bed, both are comfortable. Touch base with Kevin, he very nice and helpful can answers any additional questions. Check out Adams Falls trail very easy short hike to great views.. Granby lake and Grand Lake area 20 min drive.

Responds fast! avg. 11 minutes

Match: Shared indoor pool Swimming pool

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Price per night from

$109

Responds fast! avg. 11 minutes

Match: Shared indoor pool Swimming pool

All filters match

Price per night from

$98

Mountain Haven: Fraser's Paradise Escape with Pool & Hot Tub Amenitie

Fraser townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 32 minutes

Match: Shared indoor pool Swimming pool

All filters match

Price per night from

$335

Charming Log Cabin for Peaceful Mountain Getaway!

Black Hawk log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Shared indoor pool Swimming pool

All filters match

Price per night from

$218

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