Winter Park Vacation Rental Getaways


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  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
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  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

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

Zephyr 2419: Total convenience & comfort in the heart of ...

Winter Park
Description: This stunning condo has vaulted ceilings throughout, skylights in the bedroom, plus it'...
Condo 1 / 1 / 4

$100 - $468
Per Night

$700 - $3276
Per Week

Base Camp 472: Live your vacation dream in this large, lu...

Winter Park
Description: True mountain elegance is this beautifully isolated ski-in/ski-out condo backed up in t...
Condo 4 / 5 / 11

$382 - $1540
Per Night

$2674 - $10780
Per Week

Trademark 62: Spacious Old Town townhome with unbeatable ...

Winter Park
Description: Picture windows offer unbeatable views of the divide and ski slopes in this spacious to...
Condo 4 / 4 / 10

$231 - $908
Per Night

$1617 - $6356
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

Silverado I A202

Winter Park
Located in the town of Winter Park, Colorado, this premier vacation rental condo is bright and beaut...
Condo 2 / 2 / 4

*
Online booking available

$129 - $325
Per Night

$903 - $2275
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

Sawmill Station 300: Modern townhome in quiet downtown Wi...

Winter Park
Description: This rare end-unit town home is surrounded by open space. Enjoy the amenities such as t...
Condo 3 / 3 / 8

$179 - $725
Per Night

$1253 - $5075
Per Week

Iron Horse Resort 3084

Winter Park
Studio vacation condo at the Iron Horse, just steps from the Winter Park ski area. A 455 square foot...
Condo 0 / 1 / 4

*
Online booking available

$79 - $198
Per Night

$553 - $1383
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

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

Winter Park
Four BR 3 Bath Luxury Trademark Townhome in the heart of old town. Four Bed 3 Bath Luxury Trademark...
Condo 4 / 3 / 11

*
Online booking available

$275 - $895
Per Night

$1925 - $6265
Per Week

Zephyr 1703: Three BR Zephyr Condo looking over the slope...

Winter Park
Description: This THREE bedroom Zephyr condo sits on the 7th floor in the Slopeside building, just a...
Condo 3 / 3 / 10

$325 - $1320
Per Night

$2275 - $9240
Per Week

Fraser Crossing 3418: Modern studio at Winter Park Resort

Winter Park
Description: This spacious studio is perfect for small families or friends. You’ll love the brand ne...
Condo 0 / 1 / 4

$80 - $363
Per Night

$560 - $2541
Per Week

Two Bedroom Deluxe Condo

Winter Park
Two Bedroom Deluxe Condo Unit Description: This unit offers all the amenities of home with convenie...
Condo 2 / 3 / 8

*
Online booking available

$258 - $509
Per Night

$1806 - $3563
Per Week

Fully Remodeled Ski in Ski out Studio at the full service...

Winter Park
Fully Remodeled Ski in Ski out Studio at the full service Iron Horse Resort. This studio underwent ...
Condo 0 / 1 / 4

*
Online booking available

$50 - $245
Per Night

$350 - $1715
Per Week

Ski in Ski out slope side building one BR at the Zephyr M...

Winter Park
Ski in Ski out slope side building one BR at the Zephyr Mountain Lodge. Zephyr Mountain Lodge is ab...
Condo 1 / 1 / 4

*
Online booking available

$75 - $295
Per Night

$525 - $2065
Per Week

Beautifully upgraded 2 bed 2 bath with divide and river v...

Winter Park
Beautifully upgraded 2 bed 2 bath with divide and river views! Sleeps 6 to 8 Beautifully upgraded 2...
Condo 2 / 2 / 8

*
Online booking available

$150 - $245
Per Night

$1050 - $1225
Per Week

Fraser Crossing 3506: Hop, skip & a jump to the lifts fro...

Winter Park
Description: This 1,200 square foot condo offers extra sleeping room, cozy mountain décor, and conve...
Condo 2 / 2 / 8

$180 - $655
Per Night

$1260 - $4585
Per Week

Lakota 106: Get swept off your feet in this stunning thre...

Winter Park
Comfort and beauty are seamlessly sewn together in this three bedroom townhome located in the scenic...
Condo 3 / 3 / 9

$165 - $1050
Per Night

$1155 - $7350
Per Week

Founders Pointe 4357: Ski home for lunch at this modern &...

Winter Park
Description: This spacious condo has tons to offer, from the beautiful full kitchen with granite cou...
Condo 2 / 2 / 6

$199 - $721
Per Night

$1393 - $5047
Per Week

Fraser Crossing 3409: First-class accommodation & easy ac...

Winter Park
Description: This stylish one bedroom allows you to relax and enjoy your mountain getaway. Located ...
Condo 1 / 1 / 4

$95 - $435
Per Night

$665 - $3045
Per Week

2 BR 2 Bath in the town of Winter Park 5 minutes to the s...

Winter Park
2 BR 2 Bath in the town of Winter Park 5 minutes to the ski area. Crestview is a cozy complex of 75...
Condo 2 / 2 / 6

*
Online booking available

$80 - $275
Per Night

$560 - $1925
Per Week

Bridgers Cache Chambers House

Winter Park
Enjoy this spectacular, custom built, vacation rental home at the base of Mary Jane. From the moment...
Home 5 / 5 / 17

*
Online booking available

$1569 - $1779
Per Night

$10983 - $12453
Per Week

Base Village Loft 101: Enjoy the utmost comfort at Winter...

Winter Park
This is the best location and largest property in the heart of The Village at Winter Park Resort, ju...
Condo 4 / 4 / 12

$385 - $1705
Per Night

$2695 - $11935
Per Week

Luxurious 3 bed 3 bath home 2 mins from Winter Park with ...

Winter Park
Luxurious 3 bed 3 bath home 2 mins from Winter Park with Private Shuttle. Luxurious and roomy 3 bed...
Home 3 / 4 / 8

*
Online booking available

$195 - $695
Per Night

$1365 - $4865
Per Week

 

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