Vacation Rentals & Villas in Winter Park

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174 villas

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Match: Children's pool Golf course on site or within 15 min walk

All filters match

Price per night from

$172

Match: Children's pool Golf course on site or within 15 min walk

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Price per night from

$283

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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: Children's pool, 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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$313

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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

1 of 2 match: Children's pool, 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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$224

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

Keystone condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$144

1 of 2 match: Children's pool, 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: Children's pool, 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: Children's pool, 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: Children's pool, 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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

Updated Condo/Private Patio/Central Location

Dillon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 55 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$129

Swans Nest Villa 1601

Breckenridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$121

Highland Greens Lodge 305

Breckenridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$121

Private Hot Tub, Beautiful Views, 208 Tenderfoot

Dillon house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$493

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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$419

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$335

Ski-in, Ski-out Bliss at Granby Ranch Resort - Brand New!

Granby townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$239

Cool Condo with Trestle Bike Park Access

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

Condo On Keystone Lake/Pool and Hot Tub Access

Keystone condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$172

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$383

Custom Remodeled Kitchen/Huge Patio/Pool Access

Keystone townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$172

1 of 2 match: Children's pool, 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: Children's pool, 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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$129

1 of 2 match: Children's pool, 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: Children's pool, 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: Children's pool, 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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$434

Highland Greens Spruce

Breckenridge townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$226

1 of 2 match: Children's pool, 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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

Exceptional Mountain and Lake Views! 303D

Dillon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$172

Large Townhome, Exceptional Views, Hot Tub, Pool, Private Garage 97A

Wildernest condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$234

Vintage Ski Condo in Quiet Setting. Wood Fireplace, Hot Tubs, Pool. BB103

Wildernest condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$122

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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$203

Viewing 38 of 174
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