Winter Park Vacation Rental Getaways


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  • Beach Front
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  • Ocean View
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  • Lake View
  • Ski in/out
  • Walk to Slopes
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Sort by: Type BR/BA/Sleeps Price

Sport Studio

Winter Park
Sport Studio Unit Description: This sport studio condo unit is ideal for a couple or small family. ...
Condo 0 / 1 / 4

*
Online booking available

$103 - $259
Per Night

$721 - $1813
Per Week

Hi Country Haus Bldg 15#13

Winter Park
BEDS: King in Master, Two Twin Beds in Second Bedroom and Queen Sleeper Sofa in the Living Room; UNI...
Condo 2 / 1 / 6

*
Online booking available

$89 - $223
Per Night

$623 - $1558
Per Week

Hi Country Haus Bldg 24#6

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

Fraser Crossing 3623: Beautiful penthouse with vaulted ce...

Winter Park
Description: The rare vaulted ceilings give this condo an open feel and are a constant reminder that...
Condo 1 / 1 / 4

$90 - $402
Per Night

$630 - $2814
Per Week

Founders Pointe 4457: Convenient and Cozy Two BR Condo Ri...

Winter Park
Description: Amazing Views, convenience and comfort all in one with this spectacular condo. Enjoy th...
Condo 2 / 2 / 6

$180 - $655
Per Night

$1260 - $4585
Per Week

Lakota 502: Relax in sheer luxury in this Lakota townhome...

Winter Park
Lakota 502 is situated just across the highway from Winter Park Ski Resort in an exclusive neighborh...
Condo 3 / 3 / 10

$217 - $853
Per Night

$1519 - $5971
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

Fraser Crossing 3523: Perfect slope views from this moder...

Winter Park
Description: This brand new condo is right in the middle of it all at the Winter Park Resort. Just a...
Condo 1 / 1 / 4

$90 - $402
Per Night

$630 - $2814
Per Week

Red Quill 305: Conveniently located high-end town home i...

Winter Park
Description: This high-end town home is located right in downtown Winter Park, within easy walking d...
Condo 3 / 4 / 8

$179 - $699
Per Night

$1253 - $4893
Per Week

Cozy and comfortable 1 BR ski in ski out condo with a ful...

Winter Park
Cozy and comfortable 1 BR ski in ski out condo with a full kitchen!!! Cozy and comfortable 1 bedroo...
Condo 1 / 1 / 4

*
Online booking available

$55 - $325
Per Night

$385 - $2275
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

Winter Park Place 18: Luxurious & convenient mtn getaway ...

Winter Park
Description: You’ll feel spoiled with a brand new high-end kitchen, flat screen TV, and spacious liv...
Condo 2 / 2 / 6

$116 - $457
Per Night

$812 - $3199
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

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

Lakota 106: Get swept off your feet in this stunning thre...

Winter Park
Comfort and beauty are seamlessly sewn together in this three bedroom townhome located in the scenic...
Condo 3 / 3 / 9

$179 - $699
Per Night

$1253 - $4893
Per Week

Zephyr Mountain Lodge - Z2411

Winter Park
Slope side views from this 4th floor vacation condo rental at Winter Park Resort's premier ski-in/sk...
Condo 2 / 2 / 6

*
Online booking available

$150 - $500
Per Night

$1050 - $3500
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

4 bed 3.5 bath Lakota home with hot tub 1/2 mile from Win...

Winter Park
4 bed 3.5 bath Lakota home with hot tub 1/2 mile from Winter Park base!! 4 bed 3.5 bath Lakota town...
Condo 4 / 4 / 12

*
Online booking available

$195 - $695
Per Night

$1365 - $4865
Per Week

Fraser Crossing 3611: Luxurious penthouse condo, located ...

Winter Park
Description: This new top-floor condo offers direct slope views, and is among the best in the buildi...
Condo 2 / 2 / 8

$199 - $721
Per Night

$1393 - $5047
Per Week

Ski in Ski out slopeside building one BR at the Zephyr Mo...

Winter Park
Ski in Ski out slopeside building one BR at the Zephyr Mountain Lodge. Zephyr Mountain Lodge is abo...
Condo 1 / 1 / 4

*
Online booking available

$75 - $295
Per Night

$525 - $2065
Per Week

Base Camp 492: Huge, elegant townhome in the exclusive Ba...

Winter Park
Description: Brand new 3-story townhome, right on the Winter Park/Mary Jane ski slopes. With plush l...
Condo 4 / 5 / 10

$361 - $1485
Per Night

$2527 - $10395
Per Week

Base Village Loft 109: Coveted Base Village Loft in the h...

Winter Park
Description: This luxurious one-level loft is located right in the new Village at Winter Park. This ...
Condo 3 / 2 / 10

$357 - $1364
Per Night

$2499 - $9548
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

$229 - $575
Per Night

$1603 - $4025
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

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

 

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