Vacation Rentals & Villas in Winter Park

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44 villas

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Responds fast! avg. 2 hours 32 minutes

Match: Shared outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$190

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

Match: Shared outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$239

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

Match: Shared outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$142

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 outdoor pool (heated) Golf course on site or within 15 min walk

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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

Match: Shared outdoor pool (heated) Golf course on site or within 15 min walk

All filters match

Price per night from

$190

Responds fast! avg. 2 hours 32 minutes

Match: Shared outdoor pool (heated) Golf course on site or within 15 min walk

All filters match

Price per night from

$155

Responds fast! avg. 2 hours 32 minutes

Match: Shared outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$215

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 outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$118

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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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$239

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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$419

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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$203

Mountain Opulence: Townhome with Private Hot Tub, Overlooking Winter Park Resort

Winter Park townhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$540

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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

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Price per night from

$479

Modern Comfort in the Heart of Winter Park with Resort Shuttle

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$166

Alpine Chic Escape: New Ski Town Condo - Shuttle Service, Shared Hot Tub

Winter Park condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$166

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$215

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$179

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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$179

NEW High-Altitude Hideaway at Lakota Townhomes

Winter Park house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$960

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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

Peak Season Paradise: Ski Resort Luxury Meets Summer Relaxation

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$299

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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$155

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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$227

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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$155

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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), 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: Shared outdoor pool (heated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$275

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$173

Great rentals within 20 miles that match your search

Responds fast! avg. 11 minutes

Match: Shared outdoor pool (heated) Golf course on site or within 15 min walk

All filters match

Price per night from

$202

“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 outdoor pool (heated) Golf course on site or within 15 min walk

All filters match

Price per night from

$110

Responds fast! avg. 11 minutes

Match: Shared outdoor pool (heated) Golf course on site or within 15 min walk

All filters match

Price per night from

$95

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