Vacation Rentals & Villas in Winter Park

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77 villas

Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Dishwasher Pets allowed

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Price per night from

$259

Beautiful Mountain Lodge-Ski, Hike, Bike, Relax..

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

Match: Dishwasher Pets allowed

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Price per night from

$573

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Dishwasher Pets allowed

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Price per night from

$215

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Dishwasher Pets allowed

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Price per night from

$334

Responds fast! avg. 2 hours 32 minutes

Match: Dishwasher Pets allowed

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Price per night from

$179

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

Match: Dishwasher Pets allowed

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Price per night from

$142

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Dishwasher Pets allowed

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Price per night from

$186

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$215

Trailhead Lodges 721

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Dishwasher Pets allowed

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Price per night from

$132

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

Match: Dishwasher Pets allowed

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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

Match: Dishwasher Pets allowed

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Price per night from

$179

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Riverfront Upscale remodel in great location

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Dishwasher, Pets allowed

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Price per night from

$305

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: Dishwasher, Pets allowed

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Price per night from

$155

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: Dishwasher, Pets allowed

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Price per night from

$540

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Dishwasher, Pets allowed

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Price per night from

$147

Zephyr Mountain Lodge Slopeside 1420

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$209

Founders Pointe 4355

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$224

Snowblaze A23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$117

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: Pets allowed, Dishwasher

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Price per night from

$239

Winter Wonderland: Hot Tub Getaway in Grand Park with Heated Garage

Winter Park house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$347

Alpine Hideaway: Private Hot Tub in Ideal Mountain Haus, 10-Min Shuttle to

Winter Park townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$407

2bd/2bath Condo in Town of Winter Park - Ski, Bike, Music!

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$372

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$184

The Condo at The Gondo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$179

Hideaway Station TE-209

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$147

Trailhead Lodges 211

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$147

Base Camp 490

Winter Park condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Pets allowed, Dishwasher

1 of 2 filters match

Price per night from

$517

Founders Pointe 4473

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Dishwasher

1 of 2 filters match

Price per night from

$149

Timber Fox 1403

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Dishwasher

1 of 2 filters match

Price per night from

$147

Hideaway Station Unit TE-405

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$221

Fraser Crossing 3405

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$134

Fraser Crossing 3227

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, Dishwasher

1 of 2 filters match

Price per night from

$149

Founders Pointe 4471

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Dishwasher

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Price per night from

$134

Hideaway Station Unit TS-23

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Dishwasher

1 of 2 filters match

Price per night from

$147

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: Pets allowed, Dishwasher

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: Pets allowed, Dishwasher

1 of 2 filters match

Price per night from

$166

Mountain Majesty: Panoramic Views, Hot Tub, and Easy Access to Shuttle Route!

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Dishwasher

1 of 2 filters match

Price per night from

$311

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: Pets allowed, Dishwasher

1 of 2 filters match

Price per night from

$94

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rentals in Winter Park

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