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

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

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

Founders Pointe 4541: Best views in Founders Pointe, plus...

Winter Park
Description: New luxurious condo is located at the very front of the new complex with phenomenal vie...
Condo 2 / 2 / 8

$199 - $721
Per Night

$1393 - $5047
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

Snowblaze Condominiums 301

Winter Park
BEDS: Queen Murphy bed and a Queen Sofa Sleeper; UNIT FEATURES: Flatscreen TV with a DVD player and ...
Condo 0 / 1 / 4

*
Online booking available

$79 - $198
Per Night

$553 - $1383
Per Week

Zephyr 2223: Enjoy restaurants, stores and fun right on y...

Winter Park
Description: Enjoy the convenience of being able to roll out of bed and right onto the slopes in min...
Condo 1 / 1 / 4

$100 - $468
Per Night

$700 - $3276
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

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

Winter Park
Remodeled Ski in Ski out Studio at the full service Iron Horse Resort. Everything has been fully re...
Condo 0 / 1 / 4

*
Online booking available

$50 - $245
Per Night

$350 - $1715
Per Week

Zephyr 2700: This top floor Zephyr condo offers sophistic...

Winter Park
Description: You’ll love this convenient ski in/ski out condo with a full kitchen, gas fireplace and...
Condo 2 / 2 / 7

$200 - $798
Per Night

$1400 - $5586
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

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

Zephyr 1202: Beautifully Updated Zephyr Mountain Lodge 2 ...

Winter Park
Want to feel at home but enjoy ski in out convenience of the Zephyr Slopeside Building? This is it. ...
Condo 2 / 2 / 7

$200 - $798
Per Night

$1400 - $5586
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

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

Trademark 70: Immaculate PET FRIENDLY townhome, just 1/3 ...

Winter Park
Description: This unique trademark unit offers huge windows, displaying great views of the mountains...
Condo 3 / 3 / 8

$179 - $699
Per Night

$1253 - $4893
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

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

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

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

Hi Country Haus 1016: Stay in this inviting, updated cond...

Winter Park
Description: Inviting, cozy and updated, this condo is a perfect fit for a couple or family of four....
Condo 1 / 1 / 4

$85 - $264
Per Night

$595 - $1848
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

This Home Has It All!! Comfort, space, views and modern c...

Winter Park
This Home Has It All!! Comfort, space, views and modern convenience!!!!! This home HAS IT ALL!!!! ...
Condo 3 / 4 / 10

*
Online booking available

$200 - $695
Per Night

$1400 - $4865
Per Week

Dreamcatcher 7B Rental

Winter Park
Dream Catcher 7B at Lakota is a luxurious 3 level vacation townhome with spectacular mountain views ...
Home 5 / 5 / 11

*
Online booking available

$400 - $1248
Per Night

$2800 - $8733
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

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 / 8

*
Online booking available

$100 - $595
Per Night

$700 - $4165
Per Week

 

More Getaway Locations and Properties