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Winter Park Luxury Holiday Rentals

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522 rentals in Winter Park.
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Beautiful two bedroom condo in Winter Park! Pool, hot tub, free transportation.
2 bedrooms
2 bathrooms
Sleeps 8
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Rated 'Exceptional','The Best Beaver Village Rental',Low Rates
2 bedrooms
2 bathrooms
Sleeps 6
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Mountainside Condo with Deck & Fireplace - Near the Slopes
4 bedrooms
3 bathrooms
Sleeps 12
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Relaxing Mountain Retreat!
2 bedrooms
2 bathrooms
Sleeps 8
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Cozy, CLEAN Ski-in Ski-Out Top-Floor Studio at Iron Horse
0 bedrooms
1 bathroom
Sleeps 4
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Top Floor with Beautiful Views! Great reviews! Monthly booking is available!!!
1 bedroom
1 bathroom
Sleeps 4
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Zephyr Mountain Lodge 1601
2 bedrooms
2 bathrooms
Sleeps 6
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Two Brothers Lodge
5 bedrooms
5 bathrooms
Sleeps 18
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Founders Pointe 4541
2 bedrooms
2 bathrooms
Sleeps 8
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One Block From All Restaurants And Shopping, Nightlife
1 bedroom
1 bathroom
Sleeps 5
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Save time - get the best Winter Park rentals sent straight to your email!
Riverfront-Slopeside-Walk to Resort-On Bus Route
4 bedrooms
3 bathrooms
Sleeps 12
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Fantastic downtown townhouse. Perfect for 2 families or group.
3 bedrooms
4 bathrooms
Sleeps 11
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❤ WP✦INCREDIBLE RIVER VIEWS✦Private Top Flr✦Hideaway Park✦Nightlife✦Cozy
2 bedrooms
2 bathrooms
Sleeps 8
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Beautifully Updated Luxury Condo at Affordable Price at Ideal Location!
2 bedrooms
2 bathrooms
Sleeps 6
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5th Floor With Beautiful views! Full-kitchen! Monthly booking is available!
1 bedroom
1 bathroom
Sleeps 4
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Beautiful Winter Park Townhouse- Downtown, Great Mtn Views, Private Hot Tub!
3 bedrooms
4 bathrooms
Sleeps 8
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One block from all restaurans, shopping and nightlife.
2 bedrooms
2 bathrooms
Sleeps 6
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Luxury 3 Bdrm, 3.5 Bath Townhome in Downtown WP
3 bedrooms
4 bathrooms
Sleeps 8
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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
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Luxury Estate- Close to Village- Well Stocked and Beautifully Furnished
5 bedrooms
6 bathrooms
Sleeps 18
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Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out
1 bedroom
1 bathroom
Sleeps 5
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Winter Park Founders Pointe Slope Side Studio Steps To Base Area
1 bedroom
1 bathroom
Sleeps 4
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2BR/2BA **Just Read Our Reviews!** Beautiful Condo & Grt Value!
2 bedrooms
2 bathrooms
Sleeps 8
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Large, Luxury Private Home in Downtown Winter Park on Vasquez Creek*
8 bedrooms
9 bathrooms
Sleeps 25
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Oversized Zephyr Corner Unit, Walk Out Patio Entrance, Ski In/Out, 1 Bdrm/1 Bath
1 bedroom
1 bathroom
Sleeps 4
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Spacious Retreat With Great Amenities!
3 bedrooms
3 bathrooms
Sleeps 8
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A Real Ski-in Ski-Out Unit
1 bedroom
1 bathroom
Sleeps 4
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New Luxury Unit: Downtown, On Ski Shuttle, Pool/HotTub, Pets OK, Back to Forest
3 bedrooms
2 bathrooms
Sleeps 8
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Lakota Reserve - Luxurious Six Bedroom Home Near Winter Park Resort
6 bedrooms
7 bathrooms
Sleeps 18
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Gorgeous Condo | Private Views from Balcony | Walk To The Best Restaurants
3 bedrooms
3 bathrooms
Sleeps 10
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Heated Pool! Steps to dining & shops, sledding hill views!
3 bedrooms
3 bathrooms
Sleeps 8
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Large Glass Front with Beautiful Mountain Views
2 bedrooms
2 bathrooms
Sleeps 6
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Great Ski Condo Only 50 Ft Walk To The Lifts
1 bedroom
1 bathroom
Sleeps 6
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Winter Park Mountain Views with Private Hot Tub
3 bedrooms
3 bathrooms
Sleeps 9
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Penthouse Sport Studio - Ski-In/out - Fireplace - Balcony - Iron Horse Resort
1 bedroom
1 bathroom
Sleeps 4
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Luxury 5 br 4.5 bath 2 Masters! Across from Winter Park Ski Resort Sleeps 12
5 bedrooms
5 bathrooms
Sleeps 12
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Zephyr Mtn Lodge Slopeside - True ski-in / ski-out at WP base - UPGRADES 2017-18
2 bedrooms
2 bathrooms
Sleeps 10
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Slopeside Paradise--3 BR, 2.5 Bath 2 Minute Shuttle Ride to the slopes!
3 bedrooms
3 bathrooms
Sleeps 14
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PET-FRIENDLY | The Coolest & Newest: 4 Bedroom Downtown Condo w/ Views | Sleeps
4 bedrooms
3 bathrooms
Sleeps 10
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Creekside 3-br ski condo w/fireplace, scenic views, free shuttle to slopes
3 bedrooms
2 bathrooms
Sleeps 7
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Ski-in Ski-Out One Bedroom Condo at the Iron Horse
1 bedroom
1 bathroom
Sleeps 6
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Upscale 3BR In Town with Pool, Walking Distance To Shops/Restaurants/Park
3 bedrooms
3 bathrooms
Sleeps 8
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Trailhead Lodges 723
3 bedrooms
3 bathrooms
Sleeps 8
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2 Bedroom -Great Ski Area Views, Reasonable Rates
2 bedrooms
2 bathrooms
Sleeps 7
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Hot Tub, Pool Table HUGE Master Suite & More - WOW
5 bedrooms
4 bathrooms
Sleeps 16
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Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort
1 bedroom
1 bathroom
Sleeps 5
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Borders National Forest Trail Head For Amazing Winter and Summer Activities
4 bedrooms
3 bathrooms
Sleeps 12
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PET-FRIENDLY | Walk To Resort | Ski Home For Lunch | Hot Tub | Huge Views
5 bedrooms
6 bathrooms
Sleeps 17
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Boutique hotel style in a family-friendly 2-bed condo, free shuttles to Resort
2 bedrooms
2 bathrooms
Sleeps 7
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