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

Beaver Village Condominiums #0431

Winter Park
Large and spacious Winter Park condo, conveniently located close to town and minutes from Winter Par...
Condo 3 / 2 / 8

*
Online booking available

$145 - $465
Per Night

$1015 - $3255
Per Week

Beaver Village Condominiums #1911

Winter Park
This classic Winter Park two bedroom condo has all that you need for your vacation. Full kitchen com...
Condo 2 / 2 / 7

*
Online booking available

$120 - $390
Per Night

$840 - $2730
Per Week

Snowblaze Condominiums 310

Winter Park
This studio condo rental is located at SnowBlaze in downtown Winter Park, just 2 miles from the Wint...
Condo 0 / 1 / 4

*
Online booking available

$79 - $207
Per Night

$553 - $1449
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

$579 - $973
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

Tastefully remodeled 2 bed 2 bath in Old Town Winter Park!!

Winter Park
This is a very spacious and tastefully remodeled 2 Bedroom 2 Bath in Old Town Winter Park. Enjoy th...
Condo 2 / 2 / 6

*
Online booking available

$100 - $295
Per Night

$700 - $2065
Per Week

Beaver Village Condominiums #0723R

Winter Park
Totally remodeled one bedroom one bathroom condo featuring stainless steel appliances and granite co...
Condo 1 / 1 / 4

*
Online booking available

$100 - $305
Per Night

$700 - $2135
Per Week

Beaver Village Condominiums #1822

Winter Park
Nicely updated Winter Park two bedroom condo has all that you need for your vacation. Full kitchen c...
Condo 2 / 2 / 6

*
Online booking available

$120 - $390
Per Night

$840 - $2730
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

$295 - $995
Per Night

$2065 - $6965
Per Week

Nicely Updated Ski in Ski out Studio at the full service ...

Winter Park
Nicely Updated Ski in Ski out Studio at the full service Iron Horse Resort . Tasteful d├ęcor, muted...
Condo 0 / 1 / 4

*
Online booking available

$55 - $250
Per Night

$455 - $1645
Per Week

Very cozy ski in/out 2 bed 3 bath with Lots of room for 6...

Winter Park
Very cozy ski in/out 2 bed 3 bath with Lots of room for 6. Condo sleeps 8 This is a very cozy and c...
Condo 2 / 3 / 6

*
Online booking available

$145 - $395
Per Night

$1015 - $2765
Per Week

Beaver Village Condominums #0824

Winter Park
A warm interior will greet you as you enter this lovely updated two bedroom two bathroom condo. Gues...
Condo 2 / 2 / 7

*
Online booking available

$120 - $390
Per Night

$840 - $2730
Per Week

Beaver Village Condominiums #1523R

Winter Park
Basic two bedroom one bathroom condominium in cul de sac 15 - 20. Full kitchen, living room and dini...
Condo 1 / 1 / 4

*
Online booking available

$100 - $305
Per Night

$700 - $2135
Per Week

Ski in Ski out Studio at Iron Horse Resort.

Winter Park
This fourth floor unit has great peaceful views from the balcony. You can watch skiers make their w...
Condo 0 / 1 / 4

*
Online booking available

$65 - $225
Per Night

$455 - $1575
Per Week

Beaver Village Condominiums #0124R

Winter Park
Light and bright condo! You will enjoy this one bedroom one bathroom Winter Park condo located in th...
Condo 1 / 1 / 4

*
Online booking available

$100 - $305
Per Night

$700 - $2135
Per Week

Beaver Village Condominiums #1622R

Winter Park
Beautifully updated one bedroom condo. The kitchen has been upgraded with stainless steel appliances...
Condo 1 / 1 / 4

*
Online booking available

$100 - $305
Per Night

$700 - $2135
Per Week

IN3-D At Dreamcatcher

Winter Park
The Gourmet Cook or anyone that prefers a high end kitchen, will absolutely love this beautiful cust...
Home 5 / 5 / 13

*
Online booking available

$710 - $1470
Per Night

$4970 - $10290
Per Week

Ski in Ski out Zephyr Slopeside Bldg w/views. 2 BR sleeps...

Winter Park
Ski in Ski out Zephyr Slopeside Bldg w/views. 2 BR sleeps 10!!! This unit is 40 ft to the elevator....
Condo 2 / 2 / 10

*
Online booking available

$195 - $625
Per Night

$1365 - $4375
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

$85 - $295
Per Night

$595 - $2065
Per Week

Ski in Ski Out One Bedroom at Zephyr Mountain Lodge

Winter Park
This is a one bedroom unit with awesome views overlooking the base area. Only steps away from the el...
Condo 1 / 1 / 4

*
Online booking available

$95 - $325
Per Night

$665 - $2275
Per Week

Beaver Village Condominiums #1112

Winter Park
Contemporary furnishings, decor and accessories take you back to the 60's and 70's but with a modern...
Condo 3 / 2 / 12

*
Online booking available

$145 - $465
Per Night

$1015 - $3255
Per Week

Beaver Village Condominiums #0222R

Winter Park
Bright new lighting and an updated kitchen really make this condo stand out. The one bedroom one bat...
Condo 1 / 1 / 4

*
Online booking available

$100 - $305
Per Night

$700 - $2135
Per Week

Beaver Village Condominiums #1822R

Winter Park
Nicely updated Winter Park one bedroom condo has all that you need for your vacation. Full kitchen c...
Condo 1 / 1 / 4

*
Online booking available

$100 - $305
Per Night

$700 - $2135
Per Week

Iron Horse Resort 3023

Winter Park
A one bedroom vacation condo at the Iron Horse Resort, just steps from the Winter Park ski area. Thi...
Condo 1 / 1 / 6

*
Online booking available

$119 - $293
Per Night

$833 - $2051
Per Week

Mary Jane Chalet

Winter Park
Get the real mountain experience staying at the Mary Jane Chalet located on Forest Trail, just 1.5 m...
Home 6 / 3 / 14

*
Online booking available

$220 - $765
Per Night

$1540 - $5355
Per Week

 

More Getaway Locations and Properties