Winter Park Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Trailhead Lodges 512: Swim, ski or bike from this great d...

Winter Park
Description: This top-notch condo boasts pristine cleanliness, a brand new, very thick sofa bed, be...
Condo 1 / 1 / 4

$100 - $500
Per Night

$700 - $3500
Per Week

Four Bed 3 Bath Luxury Trademark Townhome in the heart of...

Winter Park
Four Bed 3 Bath Luxury Trademark Townhome in the heart of old town. Very comfortable and tastefully ...
Condo 4 / 3 / 10

*
Online booking available

$275 - $895
Per Night

$1925 - $6265
Per Week

Sundance West 5

Winter Park
Sundance West #5 is a 3 bedroom- 2 level rental home that is a great place to bring the family. Loca...
Home 3 / 3 / 10

*
Online booking available

$150 - $398
Per Night

$1050 - $2783
Per Week

Telemark 516: Cozy & modern condo in the Telemark neighbo...

Winter Park
Description: Fantastic location, pristine views, stunning condo! You can relax in this cozy home aft...
Condo 1 / 1 / 4

$115 - $395
Per Night

$805 - $2765
Per Week

Walk to the slopes from this Founders Point two BR with A...

Winter Park
Walk to the slopes from this Founders Point two BR with Awesome views!! This top floor unit with ca...
Condo 2 / 2 / 6

*
Online booking available

$100 - $550
Per Night

$700 - $3850
Per Week

Red Quill 509: Relax in elegant comfort in this modern Do...

Winter Park
Description: You’ll love your stay in this gorgeous end unit, conveniently located in the heart of d...
Condo 4 / 4 / 10

$295 - $908
Per Night

$2065 - $6356
Per Week

Red Quill 305: Conveniently located high-end town home i...

Winter Park
Description: This high-end town home is located right in downtown Winter Park, within easy walking d...
Condo 3 / 4 / 8

$179 - $699
Per Night

$1253 - $4893
Per Week

Wow!! The absolutely nicest Fully remodeled 2 bed 2 bath ...

Winter Park
Wow!! The absolutely nicest Fully remodeled 2 bed 2 bath condo at Beaver. WOW!! The absolutely nic...
Condo 2 / 2 / 6

*
Online booking available

$95 - $325
Per Night

$665 - $2275
Per Week

Telemark 588: Picture perfect townhome close to all the c...

Winter Park
Feel instantly at home in this newly built and beautifully furnished Winter Park townhome. The loca...
Condo 2 / 2 / 6

$137 - $534
Per Night

$959 - $3738
Per Week

Base Camp 450: Beautiful Base Camp Home Right Below The T...

Winter Park
Description: Live like the kings of elegance and style in this 3-story townhome, and enjoy the three...
Condo 4 / 5 / 13

$361 - $1485
Per Night

$2527 - $10395
Per Week

Base Village Loft 110: Highly sought after Resort Village...

Winter Park
Description: This luxurious and convenient loft offers high-end furnishings, flat screen TV’s, a gas...
Condo 3 / 3 / 10

$357 - $1364
Per Night

$2499 - $9548
Per Week

Luxurious and roomy 4 bed/bath home on Trails End Way up ...

Winter Park
Luxurious and roomy 4 bed/bath home on Trails End Way up Rendezvous Rd. Luxurious and roomy 4 bedro...
Home 4 / 4 / 10

*
Online booking available

$260 - $695
Per Night

$1820 - $4865
Per Week

Ski in Ski Out One Bedroom at Zephyr Mountain Lodge

Winter Park
This is a one bedroom unit with awesome views overlooking the basearea. Only steps away from the ele...
Condo 1 / 1 / 4

*
Online booking available

$60 - $325
Per Night

$420 - $2275
Per Week

Very cozy 2 bed/bath condo in Downtown Winter Park. Sleep...

Winter Park
Very cozy 2 bed/bath condo in Downtown Winter Park. Sleeps 6 to 8 Very comfortable and cozy 2 bed 2...
Condo 2 / 2 / 6

*
Online booking available

$100 - $275
Per Night

$700 - $1925
Per Week

Hi Country Haus 1903: Comfort & Convenience In One Neat P...

Winter Park
Description: Beautifully remodeled condo, complete with granite countertops, a brand new kitchen, an...
Condo 2 / 1 / 6

$102 - $396
Per Night

$714 - $2772
Per Week

Small Hotel Room with King Bed - Sleeps 2

Winter Park
Small hotel style room with King bed private bath. Mini-fridge and small box style TV. Internal entr...
Room/ Suite 1 / 1 / 2

*
Online booking available

$69 - $119
Per Night

$449 - $833
Per Week

Ski in Ski out riverside building one BR at the Zephyr Mo...

Winter Park
Ski in Ski out riverside building one BR at the Zephyr Mountain Lodge. This is a one bedroom unit w...
Condo 1 / 1 / 4

*
Online booking available

$75 - $325
Per Night

$525 - $2275
Per Week

Hi Country Haus Bldg 24#6

Winter Park
BEDS: Queen in Master and Queen Sofa Sleeper in the Living Room; UNIT FEATURES: 32 Inch Flat Screen ...
Condo 1 / 2 / 4

*
Online booking available

$79 - $198
Per Night

$553 - $1383
Per Week

Trailhead Lodges 633: High end townhome with only heated ...

Winter Park
Description: Beautifully vaulted ceilings, flat screen TV’s, all new furnishings, granite countertop...
Condo 2 / 2 / 6

$130 - $700
Per Night

$910 - $4900
Per Week

Sport Studio

Winter Park
Sport Studio Unit Description: This sport studio condo unit is ideal for a couple or small family. ...
Condo 0 / 1 / 4

*
Online booking available

$103 - $259
Per Night

$721 - $1813
Per Week

Downtown Winter Park - Sleeps 3 - Full Kitchen

Winter Park
Full kitchen included in the Nordic Suite for 3. This room has an outside entrance on the second lev...
Condo 1 / 1 / 3

*
Online booking available

$89 - $139
Per Night

$545 - $973
Per Week

Zephyr 1606: Open & airy top floor Zephyr condo at WPR wi...

Winter Park
Description: Brand New king Bed! This condo is updated with newer furniture, a brand new home theate...
Condo 2 / 2 / 8

$200 - $798
Per Night

$1400 - $5586
Per Week

Fraser Crossing 3611: Luxurious penthouse condo, located ...

Winter Park
Description: This new top-floor condo offers direct slope views, and is among the best in the buildi...
Condo 2 / 2 / 8

$199 - $721
Per Night

$1393 - $5047
Per Week

Founders Pointe 4345: Two minute walk to the chairlift, w...

Winter Park
Description: This gorgeous studio with fabulous views of Mary Jane is calling your name. You'll be o...
Condo 0 / 1 / 4

$85 - $380
Per Night

$595 - $2660
Per Week

Crestview 501

Winter Park
2 bedroom plus loft vacation condominium rental, located in downtown Winter Park, Colorado. Crestvie...
Condo 2 / 3 / 10

*
Online booking available

$150 - $398
Per Night

$1050 - $2783
Per Week

 

More Getaway Locations and Properties