Winter Park Vacation Rental Getaways


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  • Beach Front
  • Golf on site
  • Golf nearby
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  • 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 303: Enjoy this beautiful and spacious three BR...

Winter Park
Description: Beautiful three bedroom townhome, in the heart of downtown Winter Park and only two mil...
Condo 3 / 4 / 8

$179 - $699
Per Night

$1253 - $4893
Per Week

Very nice 2 bed / 2 bath condo at the new Trailhead prope...

Winter Park
Very nice 2 bed / 2 bath condo at the new Trailhead property in Winter Park Very nice 2 bedroom / 2...
Condo 2 / 2 / 8

*
Online booking available

$125 - $220
Per Night

$875 - $875
Per Week

3600 sq ft luxurious private home in Winter Park sleeps u...

Winter Park
3600 sq ft luxurious private home in Winter Park sleeps up to 18 Luxurious and very roomy (3600 sq...
Home 4 / 4 / 18

*
Online booking available

$470 - $940
Per Night

$2150 - $6490
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

Ski in/out one bedroom at Zephyr Mountain Lodge

Winter Park
Ski in/out one bedroom at Zephyr Mountain Lodge. Steps away from the elevator gives you easy access...
Condo 1 / 1 / 4

*
Online booking available

$60 - $295
Per Night

$420 - $2065
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

Snowblaze Condominiums A13

Winter Park
BEDS: Queen in Master Bedroom, Two Twins in Second Bedroom, and a Queen Sofa Sleeper in Living Room;...
Condo 2 / 2 / 6

*
Online booking available

$99 - $248
Per Night

$693 - $1733
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

Slopeside 202: Townhome in Old Town, just 1/4 mile from t...

Winter Park
Enjoy this townhome that sits close to the slopes and downtown Winter Park! Jump on the bus shuttle ...
Condo 3 / 3 / 11

$231 - $908
Per Night

$1617 - $6356
Per Week

Silverado II Condominiums #213

Winter Park
BEDS: Queen in Master Bedroom, Queen in Second Bedroom; UNIT FEATURES: Widescreen TV with DVD player...
Condo 2 / 2 / 6

*
Online booking available

$99 - $250
Per Night

$693 - $1750
Per Week

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

Winter Park
Description: This condo is updated with newer furniture, a brand new home theater, plus has a privat...
Condo 2 / 2 / 8

$200 - $798
Per Night

$1400 - $5586
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

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

Founders Pointe 4575: Spectacular corner unit condo with ...

Winter Park
Description: As a front corner unit, this condo has spectacular panoramic views of the mountains. Yo...
Condo 2 / 2 / 8

$199 - $721
Per Night

$1393 - $5047
Per Week

Founders Pointe 4360: Perfectly located studio at WP Reso...

Winter Park
Description: Perfect studio for families and couples! You’ll love the flat screen TV, large bathroom...
Condo 0 / 1 / 4

$80 - $363
Per Night

$560 - $2541
Per Week

Zephyr 2307: Convenient, cozy and inviting: the perfect s...

Winter Park
Description: Look right up the slopes from this 3rd floor condo in the ski in/ski out Zephyr condo. ...
Condo 2 / 2 / 6

$210 - $877
Per Night

$1470 - $6139
Per Week

Iron Horse Resort 5064

Winter Park
Enjoy the view from this roomy 455 sq. ft. studio rental located just steps from the Winter Park ski...
Condo 0 / 1 / 4

*
Online booking available

$79 - $198
Per Night

$553 - $1383
Per Week

Moose Crossing Cabin: The Vacation Home of your Dreams, l...

Winter Park
Description: Great location, beautiful private home, you’ve found it all with Moose Crossing Cabin. ...
Cabin 4 / 4 / 16

$263 - $1029
Per Night

$1841 - $7203
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

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

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

Sawmill Station 104: Spacious & Classy townhome opposite ...

Winter Park
Description: This brand new townhome is located right in the middle of town! You have three private ...
Condo 3 / 4 / 10

$179 - $725
Per Night

$1253 - $5075
Per Week

Base Village Loft 106: Top of the line Luxury Loft in the...

Winter Park
Description: Come enjoy the brand new village at Winter Park and all it has to offer. With granite c...
Condo 3 / 3 / 11

$357 - $1364
Per Night

$2499 - $9548
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

Trademark I Unit 203

Winter Park
This is a nice 1 bedroom plus a loft, plus a tiny bedroom with 2.5 bathroom vacation condo located i...
Condo 1 / 3 / 8

*
Online booking available

$149 - $373
Per Night

$1043 - $2608
Per Week

 

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