Winter Park Rentals with Pools

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41 villas in Winter Park with pools

Trailhead Lodges 524

Winter Park townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$207

Trailhead Lodges 812

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Swimming pool

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Price per night from

$147

Trailhead Lodges 212

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$132

Riverfront Upscale remodel in great location

Winter Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$304

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$172

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$172

Cozy 2 bed 2 bath Winter Park Mountain Cabin

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$144

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

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$281

Pet Friendly Riverside Delight

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

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Price per night from

$215

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: Swimming pool

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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: Swimming pool

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Price per night from

$155

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: Swimming pool

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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: Swimming pool

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Price per night from

$142

Cozy Riverside 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: Swimming pool

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Price per night from

$118

SnowBlaze Condo: Clubhouse & Mountain Views

Winter Park condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

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Price per night from

$179

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: Swimming pool

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Price per night from

$190

Luxury in Downtown Winter Park CO

Winter Park townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 15 minutes

Match: Swimming pool

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Price per night from

$277

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

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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: Swimming pool

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Price per night from

$239

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

Match: Swimming pool

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Price per night from

$94

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

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Price per night from

$155

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: Swimming pool

All filters match

Price per night from

$275

Trailhead Lodges 232

Winter Park condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$132

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

Match: Swimming pool

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Price per night from

$142

Great rentals within 20 miles that match your search

Grey Fox Condo at Granby Ranch~Ski-in/Ski-out!!

Granby condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 2 hours 39 minutes

Match: Swimming pool

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Price per night from

$167

Retreat for Relaxation & Adventure: Condo, Pool, and Shuttle

Fraser condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

All filters match

Price per night from

$179

Mountain Oasis: Roomy Condo Retreat with Outdoor Pool

Fraser condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

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Price per night from

$227

Rocky Mountain Bliss: Bike & Hike Retreat at base of the mountain

Granby condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

All filters match

Price per night from

$227

Mountain Haven: Fraser's Paradise Escape with Pool & Hot Tub Amenitie

Fraser townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

All filters match

Price per night from

$335

Elevated Bliss: Panoramic Views, 4-Minute Stroll to Lift, Private Hot Tub

Granby townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

All filters match

Price per night from

$239

Rocky Mountain Rendezvous: Basecamp for Biking and Hiking

Granby condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

All filters match

Price per night from

$166

Summertime Bliss at Granby Ranch Resort - Brand New!

Granby townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Swimming pool

All filters match

Price per night from

$239

Charming Log Cabin for Peaceful Mountain Getaway!

Black Hawk log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$218

Great Views & Rates - Winter Park Area - Colorado

Fraser apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great value, comfortable accomodations, and great owner” The owner is responsive, prompt, and courteous. We've used this condo every year for the past 11 years, and until recently, I had never even spoken to the owner- all email and all arrangements flawlessly executed, every time. Accomodations are comfortable and casual. Best feature is that this condo is directly next to the clubhouse and ski shuttle stop- very convenient! We love staying here.

Match: Swimming pool

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Price per night from

$132

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$201

“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: Swimming pool

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Price per night from

$109

Responds fast! avg. 11 minutes

Match: Swimming pool

All filters match

Price per night from

$98

The Robertson House - The Bunk Room

Parshall lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Swimming pool

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Price per night from

$228

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