Vacation Rentals & Villas in Winter Park

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56 villas

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Escape to Grand Lake: Luxury Cabin with Unmatched Views and Entertainment

Grand Lake house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 32 minutes

Match: Sea view Golf course on site or within 15 min walk

All filters match

Price per night from

$419

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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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$311

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

Powder and Pines: Slope-Seeker's Old Town Woodland Retreat

Winter Park condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$239

Slope-Side Thrills: Ski-In/Ski-Out Adventure at Granby Ranch Cond

Granby condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, 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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$203

Cozy Oasis Near Winter Park Resort | Fraser Valley Views

Fraser condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$203

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$227

Summer Retreat in Winter Park: Your Hot Tub Hideaway

Fraser condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$287

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

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$335

Alpine Chic in the Heart of Winter Park - Hot Tub Comfort in a Modern Luxury

Winter Park townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$479

Snowy Mountain Sanctuary: Your Cozy Secluded Winter Escape

Grand Lake cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

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

1 of 2 match: Sea view, 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: Sea view, 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: Sea view, 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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

Kickin it at Kicking Horse~ Ski in/out ~Sleeps 8!

Granby condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 27 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$231

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$94

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$155

Tranquil Retreat with Breathtaking Views and Inviting Hot Tub

Tabernash house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 13

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

Fraser Retreat: Cozy Townhome on Shuttle Line

Fraser townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$227

Ski Retreat for Relaxation and Adventure: Condo, Pool, and Shuttle

Fraser condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$179

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: Sea view, Golf course on site or within 15 min walk

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: Sea view, Golf course on site or within 15 min walk

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: Sea view, Golf course on site or within 15 min walk

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$118

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$155

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$239

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$215

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$227

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

Alpine Escape: Spacious Condo with Outdoor Pool

Fraser condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$227

Quiet Winter Park Townhome | Private Hot Tub | Close to Mountain Biking

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

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: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

Rustic Charm and Urban Comforts: Winter Park Cabin with Hot Tub and Wildlife

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$275

Ski Adventure Awaits | Contemporary Slopeside Condo

Granby condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Sea view, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$179

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