Villas & Vacation Rentals in Winter Park

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

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Pets allowed
Pets
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible

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

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

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19 villas

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Trailhead Lodges 812

Winter Park condo

2 bedrooms
2 bathrooms

sleeps 7

Match: Private pool Pets allowed

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Price per night from

$147

Pet Friendly Riverside Delight

Winter Park condo

2 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 32 minutes

Match: Private pool Pets allowed

All filters match

Price per night from

$215

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

Match: Private pool Pets allowed

All filters match

Price per night from

$142

Trailhead Lodges 524

Winter Park townhouse

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Pets allowed, Private pool

1 of 2 filters match

Price per night from

$206

Trailhead Lodges 212

Winter Park condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Pets allowed, Private 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, Private pool

1 of 2 filters match

Price per night from

$132

Canine-Friendly Retreat: Downtown Winter Park, Shuttle to Resort

Winter Park condo

3 bedrooms
2 bathrooms

sleeps 7

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Pets allowed, Private pool

1 of 2 filters match

Price per night from

$142

Trailhead Lodges 721

Winter Park condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Private 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: Private pool, Pets allowed

1 of 2 filters match

Price per night from

$574

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: Private 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: Private pool, Pets allowed

1 of 2 filters match

Price per night from

$540

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: Private pool, Pets allowed

1 of 2 filters match

Price per night from

$179

Rock & Stars Chalet: Luxury with Electric Car Charger, and Private Hot Tub!

Winter Park house

4 bedrooms
4 bathrooms

sleeps 12

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Private 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: Private pool, Pets allowed

1 of 2 filters match

Price per night from

$179

572 Telemark Ct

Winter Park condo

3 bedrooms
2 bathrooms

sleeps 9

1 of 2 match: Private pool, Pets allowed

1 of 2 filters match

Price per night from

$334

216 Sawyer Circle

Winter Park condo

3 bedrooms
4 bathrooms

sleeps 8

1 of 2 match: Private pool, Pets allowed

1 of 2 filters match

Price per night from

$186

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: Private pool, Pets allowed

1 of 2 filters match

Price per night from

$258

Riverfront Upscale remodel in great location

Winter Park condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Private pool, Pets allowed

1 of 2 filters match

Price per night from

$304

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

1 of 2 match: Private pool, Pets allowed

1 of 2 filters match

Price per night from

$275

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Vacation Rentals & Villas in Winter Park

Per night

19 villas

Trailhead Lodges 812

Pet Friendly Riverside Delight

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

Trailhead Lodges 524

Trailhead Lodges 212

Trailhead Lodges 232

Canine-Friendly Retreat: Downtown Winter Park, Shuttle to Resort

Trailhead Lodges 721

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

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

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

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

Rock & Stars Chalet: Luxury with Electric Car Charger, and Private Hot Tub!

SnowBlaze Condo: Clubhouse & Mountain Views

572 Telemark Ct

216 Sawyer Circle

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

Riverfront Upscale remodel in great location

Live Music Views from Hideaway Park Condo with Pool

Viewing 19 of 19
rentals in Winter Park

Also consider

Vacation Rentals & Villas in Winter Park

Per night

19 villas

Viewing 19 of 19rentals in Winter Park

Also consider

Viewing 19 of 19
rentals in Winter Park