Vacation Rentals & Villas in Winter Park

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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: Children under 5 Pets allowed

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Price per night from

$258

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Children under 5 Pets allowed

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Price per night from

$147

Riverfront Upscale remodel in great location

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children under 5 Pets allowed

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Price per night from

$304

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

Winter Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 19

Match: Children under 5 Pets allowed

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Price per night from

$574

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

Match: Children under 5 Pets allowed

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Price per night from

$540

216 Sawyer Circle

Winter Park condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Children under 5 Pets allowed

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Price per night from

$186

Trailhead Lodges 721

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children under 5 Pets allowed

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Price per night from

$132

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Children under 5 Pets allowed

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Price per night from

$215

572 Telemark Ct

Winter Park condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Children under 5 Pets allowed

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Price per night from

$334

Responds fast! avg. 2 hours 32 minutes

Match: Children under 5 Pets allowed

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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: Children under 5 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: Children under 5 Pets allowed

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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: Children under 5 Pets allowed

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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: Children under 5 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: Children under 5 Pets allowed

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Price per night from

$179

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Ultra Luxe 7000 Sqft Winter Park Cabin

Winter Park villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 36

1 of 2 match: Pets allowed, Children under 5

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Price per night from

$2,868

Beautiful, family friendly 2-2 mountain condo

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Children under 5

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Price per night from

$184

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, Children under 5

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Price per night from

$229

Cozy 2 bed 2 bath Winter Park Mountain Cabin

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Children under 5

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Price per night from

$143

NEW! IFIRESIDE MOOSE CONDO - WALK TO TOWN, FRONT DOOR SKI SHUTTLE PICK-UP

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Children under 5

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Price per night from

$281

Slope-Side Luxury: Private Hot Tub at Winter Park Resort

Winter Park townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Children under 5

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Price per night from

$479

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: Pets allowed, Children under 5

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Price per night from

$960

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: Pets allowed, Children under 5

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Price per night from

$299

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, Children under 5

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Price per night from

$142

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, Children under 5

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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, Children under 5

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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, Children under 5

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, Children under 5

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Price per night from

$118

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, Children under 5

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: Pets allowed, Children under 5

1 of 2 filters match

Price per night from

$203

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: Pets allowed, Children under 5

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: Pets allowed, Children under 5

1 of 2 filters match

Price per night from

$155

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, Children under 5

1 of 2 filters match

Price per night from

$347

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, Children under 5

1 of 2 filters match

Price per night from

$142

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, Children under 5

1 of 2 filters match

Price per night from

$275

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, Children under 5

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: Pets allowed, Children under 5

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: Pets allowed, Children under 5

1 of 2 filters match

Price per night from

$311

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