Winter Park Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Founders Pointe 4569: This walk in/out Resort studio has ...

Winter Park
Description: This primo studio sits steps from the Village at Winter Park Resort and a two minute wa...
Condo 0 / 1 / 4

$80 - $363
Per Night

$560 - $2541
Per Week

Hi Country Haus Bldg 16#3

Winter Park
BEDS: Queen in Master and Queen Murphy Bed in the Living Room; UNIT FEATURES: 31 Inch TV with DVD/VC...
Condo 1 / 1 / 4

*
Online booking available

$79 - $198
Per Night

$553 - $1383
Per Week

Sundance West 5

Winter Park
Sundance West #5 is a beautifully decorated 2,200 sq ft, 2 level rental home that is a great place t...
Home 3 / 3 / 10

*
Online booking available

$150 - $398
Per Night

$1050 - $2783
Per Week

Lakota 301: Stunning townhome in coveted Lakota neighborh...

Winter Park
It would be hard to find a property in Grand County that has better views than this brand new town h...
Condo 3 / 4 / 10

$217 - $853
Per Night

$1519 - $5971
Per Week

The House On Elk Trail

Winter Park
The House on Elk Trail is a beautiful, ranch-style vacation home located in the exclusive Elk Run su...
Home 3 / 2 / 8

*
Online booking available

$219 - $548
Per Night

$1533 - $3833
Per Week

Two Bedroom Condo

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

*
Online booking available

$158 - $403
Per Night

$1106 - $2821
Per Week

Base Camp 492: Huge, elegant townhome in the exclusive Ba...

Winter Park
Description: Brand new 3-story townhome, right on the Winter Park/Mary Jane ski slopes. With plush l...
Condo 4 / 5 / 10

$361 - $1485
Per Night

$2527 - $10395
Per Week

Trailhead Lodges 734: Balcony view of the mountains and H...

Winter Park
Description: Conveniently located in downtown Winter Park, you’re an easy walk away from the shops a...
Condo 2 / 2 / 8

$130 - $800
Per Night

$910 - $5600
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

Iron Horse Resort 4208

Winter Park
Spoil yourself slopeside in this 2 bedroom vacation rental sleeping up to 10 people. A 1525 sq. ft. ...
Condo 2 / 3 / 10

*
Online booking available

$165 - $473
Per Night

$1155 - $3308
Per Week

Fraser Crossing 3517: Fantastic location at the base of W...

Winter Park
Description: Located in the Winter Park Resort Village, you’ll love the convenience of this condo! Y...
Condo 1 / 1 / 4

$95 - $435
Per Night

$665 - $3045
Per Week

Walk to the slopes from this Fraser Crossing two bedroom.

Winter Park
This unit has Great slopeside and village views from the balcony. Fraser crossing is a newly cons...
Condo 2 / 2 / 6

*
Online booking available

$100 - $550
Per Night

$700 - $3850
Per Week

Base Camp 456: Luxurious 3-story Ski In/Ski Out Townhome ...

Winter Park
Description: Enjoy the luxury and convenience of this beautiful end-unit townhome tucked in the wood...
Condo 4 / 5 / 12

$361 - $1485
Per Night

$2527 - $10395
Per Week

Zephyr 2215: Fabulous location & decor in this updated Sk...

Winter Park
Description: This one bedroom condo has some of the best views of both the slopes and base village a...
Condo 1 / 1 / 4

$100 - $468
Per Night

$700 - $3276
Per Week

Sawmill Station 115: Huge, luxurious townhome in heart of...

Winter Park
You'll love the room this 4-bedroom town home at Sawmill Station provides for the whole family and e...
Condo 4 / 4 / 10

$231 - $908
Per Night

$1617 - $6356
Per Week

Small Hotel Room with 2 Queen Beds and 1 Twin Bed - Sleeps 5

Winter Park
Small hotel style room with Two Queen Beds and One Twin Bed, private bath. Mini-fridge and small box...
Room/ Suite 1 / 1 / 5

*
Online booking available

$89 - $129
Per Night

$579 - $903
Per Week

Cozy and beautiful 1 BR ski in/out with a full kitchen!!!

Winter Park
Cozy and comfortable 1 bedroom ski in ski out condo with a full kitchen!!! This units wonderful slo...
Condo 1 / 1 / 4

*
Online booking available

$55 - $325
Per Night

$385 - $2275
Per Week

Winter Park Place 16: best of both worlds with tranquil s...

Winter Park
Description: A favorite that guests request year after year, this condo is completely remodeled and ...
Condo 2 / 2 / 6

$116 - $457
Per Night

$812 - $3199
Per Week

Zephyr 1520: You'll love the convenience and space provid...

Winter Park
This remodeled, rare, three bedroom Zephyr condo, will provide couples and small families plenty of ...
Condo 3 / 3 / 8

$325 - $1320
Per Night

$2275 - $9240
Per Week

This is a Very tastefully remodeled ski in/out five star ...

Winter Park
This is a Very tastefully remodeled ski in/out five star 2 BR 2 bath. This is a VERY tastefully rem...
Condo 2 / 2 / 9

*
Online booking available

$95 - $495
Per Night

$665 - $3465
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

Fraser Crossing 3520: Convenient and beautiful condo, 2 m...

Winter Park
Description: Enjoy your stay in this plush studio, just a two minute walk away from the Winter Park ...
Condo 0 / 1 / 4

$80 - $363
Per Night

$560 - $2541
Per Week

Founder's Pointe 4447

Winter Park
This newly built, contemporary vacation rental property is located near The Village of Winter Park R...
Condo 1 / 1 / 4

*
Online booking available

$115 - $288
Per Night

$805 - $2013
Per Week

Fraser Crossing 3326: Perfect family ski condo at Winter ...

Winter Park
Description: Stunning corner unit condo, overlooks the village and the skating pond. Has its own 120...
Condo 2 / 2 / 8

$225 - $798
Per Night

$1575 - $5586
Per Week

Founders Pointe 4340: Spacious 2 BR Founders Point condo,...

Winter Park
Description: This fabulous lodge is located just 2 minutes from the chairlifts! Enjoy a huge outdoor...
Condo 2 / 2 / 8

$225 - $798
Per Night

$1575 - $5586
Per Week

 

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