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Winter Park Rentals with Pools

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0+ rooms, 2+ guests
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$1,000+
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137 rentals in Winter Park.
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Hi Country Haus 1909
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Trailhead Lodges 512
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Trailhead Lodges 723
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Winter Park CO from $65.00 per Ski Season night !!
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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12 other travelers have booked this property
Cozy ski condo.Winter Park,CO,USA
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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1 other traveler has booked this property
Trailhead Lodges 424
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, All pools
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Ski/Mtn Cozy Condo, Winter Park Ski Resort
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Trailhead Lodges 432
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Bright, Updated Top Floor Unit With Great Views
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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2 other travelers have booked this property
Snowblaze C24
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, All pools
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Fresh In-town condo w/W&D, pool, spa, hi-tech toys
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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7 other travelers have booked this property
Trailhead Lodges 323
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Winter Park Ski-In/Ski-Out Condo w/ Mountain Views
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Cozy Winter Park Condo Only 2 Miles from Ski Lifts
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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1 other traveler has booked this property
Winter Wonderland in WP!!!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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5 other travelers have booked this property
Winter Park Modern Riverfront-Free Shuttle-Pool/Hot Tubs-Rec Center-Walk to Town
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Affordable, Large, in Town - Pool, Hot Tubs, Great Views, Wi-Fi
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beautifully Upgraded Downtown Winter Park Condo With DirecTV(HD) and Wi-Fi
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Upscale Condo Overlooking Hideaway Park
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Downtown Winter Park Condo
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Popular 3 bedroom Remodel in best HCH building
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Remodeled, Ground Level, Family Friendly Mountain Haven Flexible cancellation
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Winter Park Condo Pool, HotTub 10% Discount If Booked Before 3/31
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Beautifully Updated Luxury Condo at Affordable Price at Ideal Location!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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True SKI IN/OUT&GREAT VIEW of slopes, gondola from every window & bed & balcony!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Winter Park 2 bdrm, Beautifully Updated, Walk2town, New Pool and Rec Center!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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2BR/2BA **Just Read Our Reviews!** Beautiful Condo & Grt Value!
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Newly Remodeled Condo On The Fraser River In Downtown Winter Park.
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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** Riverfront & Walk to Downtown Winter Park - Perfect for Ski Vacation **
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, All pools
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**Price Lowered!** Pristine Condo on the River
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Wonderful Ski in/ Ski Out Condo
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
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Beautiful Renovated Condo Within Walking Distance To Everything In Winter Park
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Remodeled, Spacious, Downtown Condo with All Amenities
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, All pools
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Luxury 2B/2B Downtown Condo, faces Hideaway Park(stage/sledding hill),Free WiFi
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Ski-in Ski Out 1 Bedroom Condo /King/Queen Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Reduced Feb! Ski-In, Ski-Out Luxury, Corner. Sleeps 6. Hot Tubs, Pool, 55' TV
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
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Mountain riverside nestled in the pines,
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Perfect Location - Family Friendly
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Amazing Condo in Downtown Winter Park!
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, All pools
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Updated Beaver Village 2 Bdrm Condo
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Cozy 1 Bedroom Hi Country Haus - on river !
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, All pools
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Cozy and convenient family condo in downtown Winter Park
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Cozy 1-bed, 1-bath condo on the Fraser river in downtown Winter Park, Colorado
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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First floor 2br condo has covered parking and it's own in-room sauna!
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Swim, Ski & Relax In The Heart Of Downtown
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, All pools
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Incredible Three Bedroom With Slope Views - Must See!
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Newest Building, Backs to all forest land,2 King Beds plus bunk beds, Sleeps 10!
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Super Stylish With Great Views And 5 Star Reviews
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Riverfront Upscale remodel in great location
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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1 other traveler has booked this property
2br/2ba Beautiful Condo In Prime Location Of Winter Park Colorado
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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