Winter Park Vacation Rental Getaways


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  • Bath
  • Sleeps
Max Price Per Week $
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  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
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  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Very Nice Four BR multi level Town Home w/Private Hot tub

Winter Park
This nice 4 bedroom multi level town home at Telemark is located off the main street in downtown Win...
Condo 4 / 3 / 12

*
Online booking available

$195 - $795
Per Night

$1365 - $5565
Per Week

Beaver Village Condominiums #0221R

Winter Park
Updated Winter Park one bedroom one bathroom condo located close to town and Winter Park Resort. New...
Condo 1 / 1 / 4

*
Online booking available

$125 - $310
Per Night

$875 - $2170
Per Week

Beaver Village Condominiums #2011

Winter Park
Luxurious bedding in the master bedroom and second bedroom give the feeling of being in a deluxe and...
Condo 2 / 2 / 6

*
Online booking available

$145 - $395
Per Night

$1015 - $2765
Per Week

Antlers At Lakota 103

Winter Park
If you are looking for convenience plus luxury, then lodging in the Antler’s complex is for you! Thi...
Home 3 / 3.5 / 8

*
Online booking available

$290 - $580
Per Night

$2030 - $4060
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 / 8

*
Online booking available

$125 - $595
Per Night

$875 - $4165
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

$50 - $295
Per Night

$385 - $2065
Per Week

Beautiful 3 bed / 3.5 bath @ Sawmill Station (located in ...

Winter Park
Beautiful 3 bed / 3.5 bath @ Sawmill Station (located in the heart of Wp) Located right next to Hid...
Condo 3 / 3.5 / 10

*
Online booking available

$150 - $595
Per Night

$1050 - $4165
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

$70 - $425
Per Night

$490 - $2975
Per Week

Beaver Village Condominiums #0322

Winter Park
Deluxe kitchen with stainless steel appliances, colorful tile floor and light wood cabinets. A new i...
Condo 2 / 2 / 7

*
Online booking available

$150 - $395
Per Night

$1050 - $2765
Per Week

Beaver Village Condominiums #2034R

Winter Park
Beautiful third floor one bedroom one bathroom condo with views of Winter Park Resort and the Contin...
Condo 1 / 1 / 2

*
Online booking available

$125 - $310
Per Night

$875 - $2170
Per Week

Beautiful modern 2 BR condo at the base (sleeps 8)! Pool ...

Winter Park
Beautiful modern 2 BR condo at the base (sleeps 8)! Pool sized Hot Tub! Looking for a clean and mod...
Condo 2 / 2 / 8

*
Online booking available

$115 - $645
Per Night

$805 - $4515
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

Beaver Village Condominiums #0922

Winter Park
This Winter Park vacation rental has a nicely updated kitchen and open floor plan. The condo is comp...
Condo 2 / 2 / 6

*
Online booking available

$150 - $395
Per Night

$1050 - $2765
Per Week

Beaver Village Condominiums #1612R

Winter Park
This one bedroom one bathroom condominium can sleep up to 4 people! The master bedroom features a ki...
Condo 1 / 1 / 4

*
Online booking available

$125 - $310
Per Night

$875 - $2170
Per Week

2 Bed 2 Bath with great views 1/2 mile from base area. Sl...

Winter Park
2 Bed 2 Bath with great views 1/2 mile from base area. Sleeps 7 to 8 Nice and bright 2 bed 2 bath T...
Condo 2 / 2 / 7

*
Online booking available

$125 - $395
Per Night

$875 - $2765
Per Week

Hi Country Haus #16-03

Winter Park
This vacation condo is a 1 bedroom, 1 bathroom located in the Hi Country Haus Condominiums, in downt...
Condo 1 / 1 / 4

*
Online booking available

$79 - $295
Per Night

$553 - $2065
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

$139 - $508
Per Night

$973 - $3556
Per Week

Iron Horse Resort 3044

Winter Park
Studio vacation condo at the Iron Horse, just steps from the Winter Park ski area. A 455 square foot...
Condo 0 / 1 / 2

*
Online booking available

$129 - $309
Per Night

$903 - $2163
Per Week

Beaver Village Condominiums #0422R

Winter Park
Simple and comfortable, this Winter Park condo is ideal for singles or couples. The one bedroom one ...
Condo 1 / 1 / 4

*
Online booking available

$125 - $310
Per Night

$875 - $2170
Per Week

Bronze 1 Bedroom/1 Bathroom Condo

Winter Park
Bronze 1 Bedroom/1 Bathroom Condo Unit Description: This one bedroom/one bathroom vacation rental i...
Condo 1 / 1 / 4

*
Online booking available

$117 - $292
Per Night

$819 - $2044
Per Week

Walk to the slopes from this Founders Point one bedroom.

Winter Park
This newer condo located in Winter Park's new resort village is your perfect getaway with top notch ...
Condo 1 / 1 / 4

*
Online booking available

$60 - $395
Per Night

$420 - $2765
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

$60 - $375
Per Night

$420 - $2625
Per Week

Newer Expansive luxurious private home in Winter Park sle...

Winter Park
Newer Expansive luxurious private home in Winter Park sleeps 15 to 18 Looking for the perfect mount...
Home 4 / 3.5 / 18

*
Online booking available

$395 - $1195
Per Night

$2975 - $8365
Per Week

Beaver Village Condominiums #1612

Winter Park
Bright new lighting and an updated kitchen really make this condo stand out. The one bedroom one bat...
Condo 2 / 2 / 8

*
Online booking available

$150 - $395
Per Night

$1050 - $2765
Per Week

A very nice one bedroom at the Iron Horse Resort. Sleeps 6

Winter Park
The Iron Horse Resort, is a full service Ski Resort which has everything you will need to make your ...
Condo 1 / 1 / 6

*
Online booking available

$75 - $395
Per Night

$525 - $2765
Per Week

 

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