Villas & Vacation Rentals in Winter Park

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Heated pool
Wireless Internet
Swimming pool
Private 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
Shared outdoor pool (unheated)
Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
Pool or snooker table
Cribs
Ceiling Fans
Clothes dryer
Games room
Table tennis
Shared outdoor pool (heated)
Swing set or jungle gym
Fax machine
Microwave
Toaster
Iron
Hair dryer
Stove
Fridge
Freezer
Linen provided
Video player
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Boat available
Housekeeping Included

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Pets allowed
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Elevator access
Wheelchair adapted
Wheelchair accessible

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Skiing – property near ski resort
Walking trips
Water sports
Horse riding

Fishing
Golf course on site or within 15 min walk
Golf within 30mins drive
Mountain Views

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26 villas

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Trailhead Lodges 812

Winter Park condo

2 bedrooms
2 bathrooms

sleeps 7

Match: Heated pool Pets allowed

All filters match

Price per night from

$147

Live Music Views from Hideaway Park Condo with Pool

Winter Park condo

2 bedrooms
1 bathroom

sleeps 6

Responds fast! avg. 2 hours 32 minutes

Match: Heated pool Pets allowed

All filters match

Price per night from

$275

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Winter Park apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$172

Cozy Winter Park Hideaway: Pool, Hot Tub, and Resort Shuttle Nearby

Winter Park condo

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$118

Ideal Location with Spacious Patio and Shared Hot Tub near Winter Park Resort

Winter Park condo

2 bedrooms
2 bathrooms

sleeps 7

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$239

Hideaway Park Gem: Ski Shuttle, Pool, and Mountain Views

Winter Park condo

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$142

Tranquil Ski Haven: Slope-Side Retreat, Ski In/Ski Out Access

Winter Park studio

Studio
1 bathroom

sleeps 2

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$155

Relaxed Slope-Side Living: Ski In/Ski Out Bliss in Cool Winter Park

Winter Park studio

Studio
1 bathroom

sleeps 4

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$190

Alpine Bliss Retreat: Ski-in/Ski-out Studio at Iron Horse, Immersed in Woodland

Winter Park studio

Studio
1 bathroom

sleeps 4

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$155

Trailside Tranquility: Iron Horse Haven, Ski-in/Ski-out 1BR Offering Stunning

Winter Park condo

1 bedroom
1 bathroom

sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$190

Trailhead Lodges 212

Winter Park condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$132

Trailhead Lodges 232

Winter Park condo

1 bedroom
2 bathrooms

sleeps 4

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$132

Trailhead Lodges 524

Winter Park townhouse

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Pets allowed, Heated pool

1 of 2 filters match

Price per night from

$206

Trailhead Lodges 721

Winter Park condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$132

Beautiful Mountain Lodge-Ski, Hike, Bike, Relax..

Winter Park house

5 bedrooms
3 bathrooms

sleeps 19

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$574

Riverfront Upscale remodel in great location

Winter Park condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$304

Summer Retreat: Dog-Friendly Condo Near Music Scene in Downtown Winter Park

Winter Park condo

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$179

Mountain Opulence: Townhome with Private Hot Tub, Overlooking Winter Park Resort

Winter Park townhouse

5 bedrooms
5 bathrooms

sleeps 12

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$540

Pet Friendly Riverside Delight

Winter Park condo

2 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$215

Wilderness Vista: Condo with Mountain Backdrop, Minutes from Winter Park Resort

Winter Park condo

3 bedrooms
4 bathrooms

sleeps 9

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$179

Rock & Stars Chalet: Luxury with Electric Car Charger, Ski Locker, and Private

Winter Park house

4 bedrooms
4 bathrooms

sleeps 12

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$419

SnowBlaze Condo: Clubhouse & Mountain Views

Winter Park condo

2 bedrooms
2 bathrooms

sleeps 7

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$179

Pet-Friendly Escape: Downtown Convenience, Resort Shuttle, Clubhouse Fun

Winter Park condo

2 bedrooms
2 bathrooms

sleeps 5

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$142

Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

Winter Park townhouse

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$258

216 Sawyer Circle

Winter Park condo

3 bedrooms
4 bathrooms

sleeps 8

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$186

572 Telemark Ct

Winter Park condo

3 bedrooms
2 bathrooms

sleeps 9

1 of 2 match: Heated pool, Pets allowed

1 of 2 filters match

Price per night from

$334

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Vacation Rentals & Villas in Winter Park

Per night

26 villas

Trailhead Lodges 812

Live Music Views from Hideaway Park Condo with Pool

Ski/Mtn Cozy Condo, Winter Park Ski Resort

Cozy Winter Park Hideaway: Pool, Hot Tub, and Resort Shuttle Nearby

Ideal Location with Spacious Patio and Shared Hot Tub near Winter Park Resort

Hideaway Park Gem: Ski Shuttle, Pool, and Mountain Views

Tranquil Ski Haven: Slope-Side Retreat, Ski In/Ski Out Access

Relaxed Slope-Side Living: Ski In/Ski Out Bliss in Cool Winter Park

Alpine Bliss Retreat: Ski-in/Ski-out Studio at Iron Horse, Immersed in Woodland

Trailside Tranquility: Iron Horse Haven, Ski-in/Ski-out 1BR Offering Stunning

Trailhead Lodges 212

Trailhead Lodges 232

Trailhead Lodges 524

Trailhead Lodges 721

Beautiful Mountain Lodge-Ski, Hike, Bike, Relax..

Riverfront Upscale remodel in great location

Summer Retreat: Dog-Friendly Condo Near Music Scene in Downtown Winter Park

Mountain Opulence: Townhome with Private Hot Tub, Overlooking Winter Park Resort

Pet Friendly Riverside Delight

Wilderness Vista: Condo with Mountain Backdrop, Minutes from Winter Park Resort

Rock & Stars Chalet: Luxury with Electric Car Charger, Ski Locker, and Private

SnowBlaze Condo: Clubhouse & Mountain Views

Pet-Friendly Escape: Downtown Convenience, Resort Shuttle, Clubhouse Fun

Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

216 Sawyer Circle

572 Telemark Ct

Viewing 26 of 26
rentals in Winter Park

Also consider

Vacation Rentals & Villas in Winter Park

Per night

26 villas

Viewing 26 of 26rentals in Winter Park

Also consider

Viewing 26 of 26
rentals in Winter Park