Vacation Rentals & Villas in Winter Park

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48 villas

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

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Golf within 30mins drive Pets allowed

All filters match

Price per night from

$257

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

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

Match: Golf within 30mins drive Pets allowed

All filters match

Price per night from

$571

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Golf within 30mins drive Pets allowed

All filters match

Price per night from

$215

Responds fast! avg. 2 hours 32 minutes

Match: Golf within 30mins drive Pets allowed

All filters match

Price per night from

$179

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

Match: Golf within 30mins drive Pets allowed

All filters match

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: Golf within 30mins drive Pets allowed

All filters match

Price per night from

$142

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

Match: Golf within 30mins drive Pets allowed

All 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

Match: Golf within 30mins drive Pets allowed

All 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

Match: Golf within 30mins drive Pets allowed

All filters match

Price per night from

$179

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Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$172

COZY CONDO ~ Ski In/ Ski Out at Winter Park Village

Winter Park studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$474

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$183

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: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$142

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, Golf within 30mins drive

1 of 2 filters match

Price per night from

$407

Summertime Splendor: Mountainside Haven Hot Tub Oasis!

Winter Park townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$479

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, Golf within 30mins drive

1 of 2 filters match

Price per night from

$347

Cozy Retreat with Private Hot Tub | Spacious Winter Haven near Downtown Winter

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$275

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, Golf within 30mins drive

1 of 2 filters match

Price per night from

$311

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: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$359

Ultra Luxe 7000 Sqft Winter Park Cabin

Winter Park villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 36

1 of 2 match: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$2,852

Luxury Mountain Haven! Family-Friendly, Ski, Bike, Hike, and Hot-Tub!

Winter Park townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$229

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, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$118

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: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$239

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: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

1 of 2 filters match

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

1 of 2 match: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

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: Pets allowed, Golf within 30mins drive

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, Golf within 30mins drive

1 of 2 filters match

Price per night from

$166

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Golf within 30mins drive

1 of 2 filters match

Price per night from

$155

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