Vacation Rentals & Villas in Winter Park

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34 villas

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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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$299

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

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: Video player, Golf course on site or within 15 min walk

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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: Video player, 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: Video player, 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: Video player, 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: Video player, 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: Video player, 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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$179

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: Video player, Golf course on site or within 15 min walk

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$275

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$227

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$203

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$540

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$239

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

1 of 2 match: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$155

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: Video player, 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: Video player, 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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$275

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$479

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$311

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

1 of 2 match: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$190

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: Video player, 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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$166

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$155

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Video player, Golf course on site or within 15 min walk

1 of 2 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

1 of 2 match: Video player, 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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$179

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$419

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$179

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$359

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: Video player, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$960

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