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Winter Park Rentals with Pools

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48 villas in Winter Park with pools

Trailhead Lodges 524

Winter Park townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 0 minutes

Match: Swimming pool

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Price per night from

$288

Trailhead Lodges 812

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 0 minutes

Match: Swimming pool

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Price per night from

$284

Trailhead Lodges 212

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 0 minutes

Match: Swimming pool

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Price per night from

$170

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

FREE Local Activities! Downtown WP-Shuttle to town or slopes Ground Floor Unit

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

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Price per night from

$118

FREE Local Activities! LOCATION! Steps away from Mainstreet. Quick Shuttle to

Winter Park condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

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Price per night from

$215

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

FREE Daily Activities! Location! Top Floor behind Hideaway Park

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

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Price per night from

$131

FREE Local Activities! Ski In/Ski Out at base of Winter Park. Iron Horse

Winter Park studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

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Price per night from

$118

FREE Local Activities! Top Floor Unit with amazing views and sunlight. Downtown

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

All filters match

Price per night from

$142

FREE Ski Rentals! Location! Walk to resturants. FREE Shuttle quick ride to

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

All filters match

Price per night from

$190

Free Local Activities! Perfect Location Downtown! Walk or jump on shuttle to

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

All filters match

Price per night from

$311

FREE Local Activities! Walk to Downtown and Free Shuttle to Winter Park! HCH

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 7 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. 1 hour 32 minutes

Match: Swimming pool

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Price per night from

$304

Upscale Downtown WinterPark 3BR Townhouse w/Garage & Private Hot Tub

Winter Park townhouse

3 bedrooms / 4 bathrooms / sleeps 9

Match: Swimming pool

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Price per night from

$416

FREE Local Activites! 3 min walk to lift! Corner Unit with View and Patio

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

All filters match

Price per night from

$215

FREE Daily Activities! LOCATION! Walk to Downtown or jump on FREE Shuttle JW

Winter Park townhouse

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

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Price per night from

$203

FREE Local Activities! Affordable and Prime Location! Walk Restaurants. FREE

Winter Park studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

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Price per night from

$83

FREE Local Activites- Top Floor Overlooking Hideaway Park. Prime location with

Winter Park condo

2 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

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Price per night from

$166

FREE Ski Rentals! -Private Hot tub and a private deck with VIEWS! 10 min walk

Winter Park condo

3 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

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Price per night from

$275

FREE Daily Activities! Luxury, Location and awesome Amenities!

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

All filters match

Price per night from

$155

FREE Local Activities! Walk to Downtown and Free Shuttle to Winter Park! HCH

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

All filters match

Price per night from

$118

Great rentals within 20 miles that match your search

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

$227

The Robertson House - The Barn Wood Room

Parshall lodge

1 bedroom / 1 bathroom / sleeps 3

Match: Swimming pool

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Price per night from

$227

The Robertson House - The Master Suite

Parshall lodge

1 bedroom / 1 bathroom / sleeps 3

Match: Swimming pool

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Price per night from

$284

The Robertson House - The Live Edge Room

Parshall lodge

1 bedroom / 1 bathroom / sleeps 3

Match: Swimming pool

All filters match

Price per night from

$227

1 Mile to ski area / Amazing Views / Pool-Hot Tub

Granby house

3 bedrooms / 2 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$286

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

Granby condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 41 minutes

Match: Swimming pool

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Price per night from

$155

Match: Swimming pool

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Price per night from

$258

3/3 MeadowRidge Townhome with Garage

Fraser townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$189

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

COZY CABIN IN HISTORIC IDAHO SPRINGS: SKI, SNOWBOARD, SOAK IN HOT SPRINGS!

Idaho Springs log cabin

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 46 minutes

Match: Swimming pool

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Price per night from

$144

Great Views & Rates - Winter Park Area - Colorado

Fraser apartment

2 bedrooms / 2 bathrooms / sleeps 8

“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

$287

COZY CABIN IN IDAHO SPRINGS NEAR SKI RESORTS AND HOT SPRINGS

Silver Plume house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 46 minutes

Match: Swimming pool

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Price per night from

$144

FREE Local Activities! Hot Tub and POOL OPEN! ON Shuttle and access to best

Fraser condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

All filters match

Price per night from

$155

FREE Daily Activities! Quiet Mountain Cabin less than 15 min from Winter Park

Tabernash house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 7 minutes

Match: Swimming pool

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Price per night from

$215

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rentals in Winter Park

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