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Swimming pool
Wireless Internet
Air conditioning
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
Sauna
Sea view
Safe
Dishwasher
Children's pool
Clothes dryer
Shared indoor pool
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Table tennis
Games room
Swing set or jungle gym
Pool or snooker table
Fax machine
Video player
Boat available
Staffed property
Private fishing lake or river
Trampoline
Climbing frame
Bicycles available
Towels provided
Linen provided
Microwave
Freezer
Fridge
Housekeeping Included

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Pets allowed
Parking
Car not required
Children under 5

Non-Smoking property
Elevator access
Wheelchair adapted
Wheelchair accessible

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Mountain Views
Golf within 30mins drive
Waterfront

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162 villas in Winter Park with pools

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Cozy Updated Condo With Great Views

Winter Park condo

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

All filters match

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

All filters match

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

All filters match

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

All filters match

Price per night from

$58

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

Winter Park house

3 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

All filters match

Price per night from

$285

Newly Remodeled Studio/Think Snow!

Winter Park studio

Studio / 1 bathroom / sleeps 3

Match: Swimming pool

All filters match

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

All filters match

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

All filters match

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

All filters match

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

All filters match

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

All filters match

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

All filters match

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

All filters match

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

All filters match

Price per night from

$82

Riverside Retreat at Hi Country Haus in Winter Park by Notable Vacation Rentals

Winter Park studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 10 minutes

Match: Swimming pool

All filters match

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

All filters match

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

All filters match

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

All filters match

Price per night from

$97

Winter Park Studio Condo - 5 Mins to Downtown!

Winter Park studio

Studio / 1 bathroom / sleeps 4

Match: Swimming pool

All filters match

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

All filters match

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

All filters match

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

All filters match

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

All filters match

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

All filters match

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

All filters match

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
rentals in Winter Park

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COVID-19 Update

Winter Park Rentals with Pools

Per night

162 villas in Winter Park with pools

Viewing 38 of 162rentals in Winter Park

Also consider

Viewing 38 of 162
rentals in Winter Park