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Winter Park Condos

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421 rentals in Winter Park.
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Rated 'Exceptional','The Best Beaver Village Rental',Low Rates, vacation rental in Winter Park

Rated 'Exceptional','The Best Beaver Village Rental',Low Rates

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy, CLEAN Ski-in Ski-Out Top-Floor Studio at Iron Horse, vacation rental in Winter Park

Cozy, CLEAN Ski-in Ski-Out Top-Floor Studio at Iron Horse

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Relaxing Mountain Retreat!, vacation rental in Winter Park

Relaxing Mountain Retreat!

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Still available for winter skiing! Mountain home great for families, vacation rental in Winter Park

Still available for winter skiing! Mountain home great for families

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Top Floor with Beautiful Views! Great reviews!  Monthly booking is available!!!, vacation rental in Winter Park

Top Floor with Beautiful Views! Great reviews! Monthly booking is available!!!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Creekside 3-br ski condo w/fireplace, scenic views, free shuttle to slopes, vacation rental in Winter Park

Creekside 3-br ski condo w/fireplace, scenic views, free shuttle to slopes

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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One Block From All Restaurants And Shopping, Nightlife, vacation rental in Winter Park

One Block From All Restaurants And Shopping, Nightlife

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Fantastic downtown townhouse. Perfect for 2 families or group., vacation rental in Winter Park

Fantastic downtown townhouse. Perfect for 2 families or group.

3 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Riverfront-Slopeside-Walk to Resort-On Bus Route, vacation rental in Winter Park

Riverfront-Slopeside-Walk to Resort-On Bus Route

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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5th Floor With Beautiful views! Full-kitchen! Monthly booking is available!, vacation rental in Winter Park

5th Floor With Beautiful views! Full-kitchen! Monthly booking is available!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful two bedroom condo in Winter Park! Pool, hot tub, free transportation., vacation rental in Winter Park

Beautiful two bedroom condo in Winter Park! Pool, hot tub, free transportation.

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Updated Luxury Condo at Affordable Price at Ideal Location!, vacation rental in Winter Park

Beautifully Updated Luxury Condo at Affordable Price at Ideal Location!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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❤ WP✦INCREDIBLE RIVER VIEWS✦Private Top Flr✦Hideaway Park✦Nightlife✦Cozy, vacation rental in Winter Park

❤ WP✦INCREDIBLE RIVER VIEWS✦Private Top Flr✦Hideaway Park✦Nightlife✦Cozy

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Winter Park Townhouse- Downtown, Great Mtn Views, Private Hot Tub!, vacation rental in Winter Park

Beautiful Winter Park Townhouse- Downtown, Great Mtn Views, Private Hot Tub!

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Condo | Private Views from Balcony | Walk To The Best Restaurants, vacation rental in Winter Park

Gorgeous Condo | Private Views from Balcony | Walk To The Best Restaurants

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Luxury 3 Bdrm, 3.5 Bath Townhome in Downtown WP, vacation rental in Winter Park

Luxury 3 Bdrm, 3.5 Bath Townhome in Downtown WP

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Ski in/out,2/2,hot tub,K & T/Q/T Bunk,memory foam Q couch/xbox/deck grill/sleep8, vacation rental in Winter Park

Ski in/out,2/2,hot tub,K & T/Q/T Bunk,memory foam Q couch/xbox/deck grill/sleep8

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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One block from all restaurans, shopping and nightlife., vacation rental in Winter Park

One block from all restaurans, shopping and nightlife.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Estate- Close to Village- Well Stocked and Beautifully Furnished, vacation rental in Winter Park

Luxury Estate- Close to Village- Well Stocked and Beautifully Furnished

5 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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New Luxury Unit: Downtown, On Ski Shuttle, Pool/HotTub, Pets OK, Back to Forest, vacation rental in Winter Park

New Luxury Unit: Downtown, On Ski Shuttle, Pool/HotTub, Pets OK, Back to Forest

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Heated Pool! Steps to dining & shops, sledding hill views!, vacation rental in Winter Park

Heated Pool! Steps to dining & shops, sledding hill views!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Zephyr Mtn Lodge Slopeside - True ski-in / ski-out at WP base - UPGRADES 2017-18, vacation rental in Winter Park

Zephyr Mtn Lodge Slopeside - True ski-in / ski-out at WP base - UPGRADES 2017-18

2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Large, Luxury Private Home in Downtown Winter Park on Vasquez Creek*, vacation rental in Winter Park

Large, Luxury Private Home in Downtown Winter Park on Vasquez Creek*

8 bedrooms
9 bathrooms
Sleeps 25
Match: Sleeps
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2BR/2BA  **Just Read Our Reviews!**  Beautiful Condo & Grt Value!, vacation rental in Winter Park

2BR/2BA **Just Read Our Reviews!** Beautiful Condo & Grt Value!

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out, vacation rental in Winter Park

Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Winter Park Founders Pointe Slope Side Studio Steps To Base Area, vacation rental in Winter Park

Winter Park Founders Pointe Slope Side Studio Steps To Base Area

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Winter Park Mountain Views with Private Hot Tub, vacation rental in Winter Park

Winter Park Mountain Views with Private Hot Tub

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Large Glass Front with Beautiful Mountain Views, vacation rental in Winter Park

Large Glass Front with Beautiful Mountain Views

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Retreat With Great Amenities!, vacation rental in Winter Park

Spacious Retreat With Great Amenities!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakota Reserve - Luxurious Six Bedroom Home Near Winter Park Resort, vacation rental in Winter Park

Lakota Reserve - Luxurious Six Bedroom Home Near Winter Park Resort

6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Slopeside Paradise--3 BR, 2.5 Bath 2 Minute Shuttle Ride to the slopes!, vacation rental in Winter Park

Slopeside Paradise--3 BR, 2.5 Bath 2 Minute Shuttle Ride to the slopes!

3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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PET-FRIENDLY | The Coolest & Newest: 4 Bedroom Downtown Condo w/ Views | Sleeps, vacation rental in Winter Park

PET-FRIENDLY | The Coolest & Newest: 4 Bedroom Downtown Condo w/ Views | Sleeps

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ski-in Ski-Out One Bedroom Condo at the Iron Horse, vacation rental in Winter Park

Ski-in Ski-Out One Bedroom Condo at the Iron Horse

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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PET-FRIENDLY | Walk To Resort | Ski Home For Lunch | Hot Tub | Huge Views, vacation rental in Winter Park

PET-FRIENDLY | Walk To Resort | Ski Home For Lunch | Hot Tub | Huge Views

5 bedrooms
6 bathrooms
Sleeps 17
Match: Sleeps
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Luxury 5 br 4.5 bath 2 Masters! Across from Winter Park Ski Resort Sleeps 12, vacation rental in Winter Park

Luxury 5 br 4.5 bath 2 Masters! Across from Winter Park Ski Resort Sleeps 12

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Borders National Forest Trail Head For Amazing Winter and Summer Activities, vacation rental in Winter Park

Borders National Forest Trail Head For Amazing Winter and Summer Activities

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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3 BR  with Private Hot Tub and views of the slopes in prestigious Lakota!!, vacation rental in Winter Park

3 BR with Private Hot Tub and views of the slopes in prestigious Lakota!!

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Upscale 3BR In Town with Pool, Walking Distance To Shops/Restaurants/Park, vacation rental in Winter Park

Upscale 3BR In Town with Pool, Walking Distance To Shops/Restaurants/Park

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Great Ski Condo Only 50 Ft Walk To The Lifts, vacation rental in Winter Park

Great Ski Condo Only 50 Ft Walk To The Lifts

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Penthouse Sport Studio - Ski-In/out - Fireplace - Balcony - Iron Horse Resort, vacation rental in Winter Park

Penthouse Sport Studio - Ski-In/out - Fireplace - Balcony - Iron Horse Resort

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly renovated, steps to restaurants, mountain views, on free bus route, vacation rental in Winter Park

Newly renovated, steps to restaurants, mountain views, on free bus route

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Remodeled, Ground Level, Family Friendly Mountain Haven   Flexible cancellation, vacation rental in Winter Park

Remodeled, Ground Level, Family Friendly Mountain Haven Flexible cancellation

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Boutique hotel style in a family-friendly 2-bed condo, free shuttles to Resort, vacation rental in Winter Park

Boutique hotel style in a family-friendly 2-bed condo, free shuttles to Resort

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Family/ Pet Friendly Updated Downtown Winter Park Condo 3BD/2BA, vacation rental in Winter Park

Family/ Pet Friendly Updated Downtown Winter Park Condo 3BD/2BA

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Oversized Zephyr Corner Unit, Walk Out Patio Entrance, Ski In/Out, 1 Bdrm/1 Bath, vacation rental in Winter Park

Oversized Zephyr Corner Unit, Walk Out Patio Entrance, Ski In/Out, 1 Bdrm/1 Bath

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Hot Tub, Pool Table HUGE Master Suite & More - WOW, vacation rental in Winter Park

Hot Tub, Pool Table HUGE Master Suite & More - WOW

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Ski In / Ski Out | Ski Home For Lunch & Apres | Private Hot Tub | Luxury Mountai, vacation rental in Winter Park

Ski In / Ski Out | Ski Home For Lunch & Apres | Private Hot Tub | Luxury Mountai

5 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Creekside Condo in Downtown Winter Park - Ideal Romantic Getaway W/SKI LOCKER!, vacation rental in Winter Park

Creekside Condo in Downtown Winter Park - Ideal Romantic Getaway W/SKI LOCKER!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Winter Park 2 bdrm, Beautifully Updated, Walk2town, Summer Getaway!, vacation rental in Winter Park

Winter Park 2 bdrm, Beautifully Updated, Walk2town, Summer Getaway!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Rocky Mountain home w/ a full kitchen, shared tennis, & amazing views, vacation rental in Winter Park

Gorgeous Rocky Mountain home w/ a full kitchen, shared tennis, & amazing views

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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