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Winter Park Rentals with Pools

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162 villas in Winter Park with pools

Cozy Updated Condo With Great Views

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$204

Cozy Winter Park Condo w/Shuttle & Hot Tub Access!

Winter Park apartment

3 bedrooms / 2 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$138

Winter Park Condo w/ Hot Tubs, 3 Mi to Ski Resort!

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$148

Winter Park CO from $65.00 per Ski Season night !!

Winter Park villa

/ 1 bathroom / sleeps 4

Responds fast! avg. 22 minutes

Match: Swimming pool

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Price per night from

$58

Timber Lake 341 (************)

Winter Park house

3 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$285

Newly Remodeled Studio/Think Snow!

Winter Park studio

Studio / 1 bathroom / sleeps 3

Match: Swimming pool

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Price per night from

$228

3BR Upscale Penthouse with Largest Deck at Base with Amazing View

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$606

Winter Park Condo on Bus Route, 2 Blocks to Dtwn!

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$131

Trailhead Lodges 524

Winter Park townhouse

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 0 minutes

Match: Swimming pool

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Price per night from

$231

Winter Park Area Family Cabin w/Mtn View & Hot Tub

Winter Park house

3 bedrooms / 3 bathrooms / sleeps 9

Match: Swimming pool

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Price per night from

$237

Cozy Winter Park Studio w/Views-Walk to Downtown!

Winter Park studio

Studio / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$91

NEW! Cozy Ski Condo w/Hot Tubs, 3 Mi to WP Resort!

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$98

Remodeled Riverside Getaway w/ Hot Tubs, Pool, Clubhouse & Shuttle to Slopes

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$154

Ski-In/Ski-Out Winter Park Condo w/ Amenity Access

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$82

Responds fast! avg. 10 minutes

Match: Swimming pool

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Price per night from

$115

Sophisticated Ski-In/Ski-Out Getaway – 1,471 Square Feet, Balcony & Fireplace

Winter Park condo

2 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$895

Trailhead Lodges 812

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 0 minutes

Match: Swimming pool

All filters match

Price per night from

$228

Trailhead Lodges 212

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 0 minutes

Match: Swimming pool

All filters match

Price per night from

$136

Charming Condo w/ Hot Tub & Heated Pool -- Walk to Downtown, Near Ski Shuttle

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$200

Condo w/ Pool + Hot Tub - Walk to DT Winter Park!

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$129

Winter Park Ski-In/Ski-Out Condo w/ Mountain Views

Winter Park apartment

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

All filters match

Price per night from

$137

Ski-In/Out Resort Condo by Mary Jane Base!

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$97

Winter Park Studio Condo - 5 Mins to Downtown!

Winter Park studio

Studio / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$101

NEW! Mtn Condo w/Ski Locker & Pools, 3Mi to Resort

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$101

Condo < ½ Mile from Shuttle to Winter Park Resort

Winter Park condo

3 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

All filters match

Price per night from

$133

Fabulous Slope-Side Lakota Living | Private Hot Tub & Magnificent Views

Winter Park townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$1,185

Ski-In/Ski-Out Winter Park Condo w/ Pool Access!

Winter Park condo

2 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$177

4Mi to Winter Park-Townhome w/Private Hot Tub

Winter Park townhouse

3 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

All filters match

Price per night from

$181

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

Cozy Condo w/ Amenities in Heart of Winter Park!

Winter Park apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$109

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

$195

Cozy ski condo.Winter Park,CO,USA

Winter Park apartment

/ 1 bathroom / sleeps 4

Match: Swimming pool

All filters match

Price per night from

$195

Iron Horse Ski-In & Ski-Out Retreat | Balcony & Fireplace | Shuttle to Town

Winter Park studio

Studio / 1 bathroom / sleeps 4

Match: Swimming pool

All filters match

Price per night from

$108

NEW! Chic Winter Park Studio: 3 Mi to the Slopes!

Winter Park studio

Studio / 1 bathroom / sleeps 4

Match: Swimming pool

All filters match

Price per night from

$119

Downtown Condo with Balcony & Fireplace | Walkable Locale by Hideaway Park

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

All filters match

Price per night from

$195

FREE Daily Activities! Location! Top Floor behind Hideaway Park

Winter Park condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 34 minutes

Match: Swimming pool

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Price per night from

$155

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

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 34 minutes

Match: Swimming pool

All filters match

Price per night from

$179

NEW! Cozy Winter Park Condo: Walk to Main Street!

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$113

Viewing 38 of 162
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