Winter Park Rentals with Pools

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52 villas in Winter Park with pools

Trailhead Lodges 524

Winter Park townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 29 minutes

Match: Swimming pool

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Price per night from

$215

Trailhead Lodges 812

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 29 minutes

Match: Swimming pool

All filters match

Price per night from

$215

Trailhead Lodges 212

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 29 minutes

Match: Swimming pool

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Price per night from

$144

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

DOWNTOWN WINTER PARK | INDOOR POOL AND HOT TUB | WALK TO MUSIC AT HIDEAWAY PARK

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

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Price per night from

$179

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

LOCATION! Walk to Music and Restaurants! Quick Shuttle to slopes

Winter Park condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

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Price per night from

$239

NEW !! DOWNTOWN WINTER PARK | HOT TUB | POOL | FITNESS ROOM

Winter Park studio

Studio / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

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Price per night from

$131

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

Outdoor Pool, Ideal Downtown location behind Hideaway Park perfect for Music!

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$142

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. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$131

Heart of Downtown Winter Park | Pool & Hot Tub | Walk to Hideaway Park for Music

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$179

WINTER PARK | POOL & HOT TUB | SHUTTLE TO RESORT

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

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Price per night from

$107

WINTER PARK PET FRIENDLY | POOL & HOT TUB | SHUTTLE TO RESORT

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

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Price per night from

$190

Ski In/Ski Out at base of Winter Park. Iron Horse

Winter Park studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$131

Luxury in Downtown Winter Park CO

Winter Park townhouse

4 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 51 minutes

Match: Swimming pool

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Price per night from

$238

Corner Unit with Large Patio short Walk to Lifts at Winter Park

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$190

Walk to Downtown | On Free Shuttle to Winter Park Resort

Winter Park townhouse

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$179

LOCATION! WALK TO MUSIC | POOL | FIRE PIT | HOT TUB | FITNESS CENTER

Winter Park studio

Studio / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$107

Pool! Top Floor Overlooking Hideaway Park, Perfect Music Location Trailhead 734

Winter Park condo

2 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$190

Private Hot Tub and a private deck with VIEWS!

Winter Park condo

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

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Price per night from

$419

DOWNTOWN WINTER PARK| LUXURY CONDO | POOL, HOT TUB and GAMEROOM

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$190

Bring your dog! Downtown Winter Park on Shuttle to Resort.

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

All filters match

Price per night from

$142

Trailhead Lodges 232

Winter Park condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 29 minutes

Match: Swimming pool

All filters match

Price per night from

$144

Great rentals within 20 miles that match your search

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. 3 hours 40 minutes

Match: Swimming pool

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Price per night from

$115

COZY CABIN IN IDAHO SPRINGS NEAR SKI RESORTS AND HOT SPRINGS

Silver Plume house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 40 minutes

Match: Swimming pool

All filters match

Price per night from

$143

FRONT RANGE CABIN IN ROCKY MOUNTAINS COLORADO

Silver Plume cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 58 minutes

Match: Swimming pool

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Price per night from

$143

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

The Robertson House - The Live Edge Room

Parshall lodge

1 bedroom / 1 bathroom / sleeps 3

Match: Swimming pool

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Price per night from

$228

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

$285

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

$228

Ski Trip! 2022/23, or Summer 2023! Fam Retreat - Resort Livng - Modrn Apt!

Granby condo

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 3 minutes

Match: Swimming pool

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Price per night from

$166

“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. 3 hours 3 minutes

Match: Swimming pool

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Price per night from

$98

MINER'S CABIN NEAR SKI RESORTS, HOT SPRINGS, WHITEWATER RAFTING

Idaho Springs house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 58 minutes

Match: Swimming pool

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Price per night from

$113

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

$132

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

Granby condo

2 bedrooms / 2 bathrooms / sleeps 5

Match: Swimming pool

All filters match

Price per night from

$155

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