Winter Park Vacation Rental Getaways


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  • Property Options
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  • Location Type
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  • Bath
  • Sleeps
Max Price Per Week $
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  • Online Booking
  • Home/Villa
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  • 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

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

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

Trailhead Lodges 724: Incredible two-BR condo right on Hi...

Winter Park
Everyone wants to stay right on Hideaway Park in downtown Winter Park but only 12 condos look over t...
Condo 2 / 2 / 6

$130 - $800
Per Night

$910 - $5600
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

Newly built, high end one BR with garage in the heart of ...

Winter Park
Newly built, high end one BR with garage in the heart of Winter Park!!!! Newly built, high end one ...
Condo 1 / 1 / 4

*
Online booking available

$75 - $295
Per Night

$525 - $2065
Per Week

Hi Country Haus Bldg 24#3

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

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

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

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. Everything has been fu...
Condo 0 / 1 / 4

*
Online booking available

$50 - $245
Per Night

$350 - $1715
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

$75 - $550
Per Night

$525 - $3850
Per Week

Very Nice, Ski in Ski Out Studio at the full service Iron...

Winter Park
Very Nice, Ski in Ski Out Studio at the full service Iron Horse Resort Very nice and cozy studio. ...
Condo 0 / 1 / 4

*
Online booking available

$50 - $225
Per Night

$350 - $1575
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

Iron Horse Resort 5023

Winter Park
This nicely laid-out rental condo is located at the Iron Horse Resort, just steps from the Winter Pa...
Condo 1 / 1 / 6

*
Online booking available

$110 - $298
Per Night

$770 - $2083
Per Week

Downtown Winter Park Condo With Mountain Views

Winter Park
Our 1200 sq. ft. 3BR, 3Bath condo is available to rent for your mountain getaway to meet everyone's ...
Condo 3 / 3 / 11

*
Online booking available

$289 - $309
Per Night

$1879 - $2163
Per Week

Base Camp 480: Exquisite Base Camp Townhome Below The Tra...

Winter Park
Description: Beautiful ski-in/ski-out property in Winter Park, with 3,000+ square feet of luxury liv...
Condo 4 / 5 / 14

$382 - $1540
Per Night

$2674 - $10780
Per Week

Iron Horse Resort 3023

Winter Park
A perfect vacation rental at the Iron Horse Resort, just steps from the Winter Park ski area. A nice...
Condo 1 / 1 / 6

*
Online booking available

$110 - $298
Per Night

$770 - $2083
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

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 - $1883
Per Night

$10983 - $13180
Per Week

Iron Horse Resort 4063

Winter Park
This roomy 455 sq. ft. studio is a perfect vacation condo located at the Iron Horse Resort, just ste...
Condo 0 / 1 / 4

*
Online booking available

$79 - $198
Per Night

$553 - $1383
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 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

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

Very nice 3 BR / 3 BA condo at the new property in the he...

Winter Park
Very nice 3 BR / 3 BA condo at the new property in the heart of Wp Very nice 3 bedroom / 3 bathroom...
Condo 3 / 3 / 8

*
Online booking available

$175 - $495
Per Night

$1225 - $3465
Per Week

Base Camp 494: Enjoy Million Dollar Living At This Amazin...

Winter Park
Description: Enjoy the seclusion and quiet of this beautiful mountain home, while being located just...
Condo 4 / 5 / 14

$361 - $1485
Per Night

$2527 - $10395
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

 

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