Vacation Rentals & Villas in Winter Park

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Alpine Villa Retreat Breckenridge

Breckenridge villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 26

Match: Golf course on site or within 15 min walk Wheelchair accessible

All filters match

Price per night from

$4,014

Match: Golf course on site or within 15 min walk Wheelchair accessible

All filters match

Price per night from

$917

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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: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$311

103 Eagle Ridge Rd B-1

Granby house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$313

Riverside Lodge Dorm Room Bunk Best Value Summit County Share bathroom 4 to 8 p

Silverthorne private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 20

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$57

Mountain condo by the creek

Georgetown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$144

Founders Pointe 4473

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$149

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: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$122

Frosty Mountain Escape in Keystone

Keystone condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$224

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$172

Champagne Powder, Walk to Lifts, Amazing Views!

Keystone hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

“Great Location!!” This condo is in a great location, close to everything you could want. The awesome views from the deck look right out to the slopes. The lifts are a 5 minute walk, or if you prefer the shuttle, the shuttle stops 20 steps from the front door. The condo is stocked with all the essentials needed for someone like myself that enjoys cooking. I will definitely be going back next season!!

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$224

Winter Park Mountain Getaway!

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$287

Trailhead Lodges 212

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$132

Hideaway Station TE-209

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$147

On Shuttle Route to Slopes/Pool and Hot Tub Access/Private Deck

Keystone condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$144

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$259

Highland Greens Lodge 210

Breckenridge apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$106

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: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$239

Slope-Side Thrills: Bike, Hike, and Stay

Granby condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$118

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

LOG CABIN Grand Lake / Columbine Lake

Grand Lake log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$316

5 Min 2 Slopes, Lake! Hot tub, Pool, Wood Fireplace, Views

Keystone condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$132

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$144

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Golf course on site or within 15 min walk, Wheelchair accessible

1 of 2 filters match

Price per night from

$147

Updated Condo/Private Patio/Central Location

Dillon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$129

Condo On Keystone Lake/Pool and Hot Tub Access

Keystone condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$172

Custom Remodeled Kitchen/Huge Patio/Pool Access

Keystone townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$172

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$157

Walk to the Gondola/Shared Hot Tub/Great Amenities

Keystone condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$129

2 Minute Walk to the Gondola/Shared Hot Tub/Private Patio

Keystone condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$129

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$129

150 yds to the Gondola/Shared Pool and Hot Tub Access/Private Patio

Keystone condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$216

Remodeled Penthouse/On Shuttle Route to the Slopes/Shared Hot Tub

Keystone condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$216

Private Garage/Walk to the Gondola in 2 Minutes/Pool and Hot Tub/Fitness Room

Keystone townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$434

Highland Greens Lodge 305

Breckenridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$121

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$147

Cozy Fraser Retreat: Family Space, Private Hot Tub, Convenient Shuttle

Fraser house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Wheelchair accessible, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

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