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Ski-in/out rentals in Winter Park Resort

Find and book unique ski-in/out homes on Airbnb

Top-rated ski-in/out rentals near Winter Park Resort

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of the condo building is illuminated by soft lighting, including blue decorative lights on the balcony. Snow blankets the ground, reflecting the gentle glow from the building. Tall evergreen trees frame the scene, adding to the winter ambiance.
Flat in Winter Park
5 out of 5 average rating, 27 reviews

NEW Ski In/Out Condo w/ Hot Tub & Balcony

Escape to a stunning new (2023) condo, located ON the ski run & just a short walk down to the Village for drinks & food! Enjoy restful nights on the luxurious king bed while the kids or friends have their own adventure in the (full bottom/twin top) bunk bed den, & transform the couch into a full bed for more friends! Gather at our inviting bar near the electric fireplace or on your balcony for après-ski fun, all while overlooking the run. Book today & discover comfort, convenience, & adventure!

Guest favourite
A tastefully arranged sleeping area features a dark green accent wall and a modern bed with neutral bedding. A stylish nightstand with a small plant and clock is positioned beside the bed, illuminated by a sleek wall-mounted lamp.
Apartment in Winter Park
4.9 out of 5 average rating, 200 reviews

Ski In/Ski Out - Modern Cozy Condo in Winter Park

Welcome to Leone’s Den. This newly renovated studio condo located at the base of Winter Park Resort. Walk less than 150 yards to the slopes! Shops, restaurants, and bars at the Village Base just across the street and a pool sized hot tub! Marvel at the beautiful mountain views from the largest hot tub in Winter Park, brand new in 2025. Enjoy the view of village and mountain landscape while enjoying the warmth of the fireplace. The studio has everything you need for an unforgettable stay.

Guest favourite
A cozy living area features a black leather sofa and an armchair positioned near a wooden coffee table. A fireplace is framed by decorative tile, while large windows provide natural light. An accent wall displays a piece of art, adding a touch of character to the space.
Flat in Winter Park
4.95 out of 5 average rating, 22 reviews

Ski-In/Ski-Out Studio

Step into comfort at this ski-in/ski-out studio at Iron Horse Condominiums in Winter Park. This first-floor condo features patio access to a heated pool, hot tubs, and grill. Perfect for families or couples, the light-filled space has cozy sleeping options, a full kitchen with a crock pot, and resort-style amenities, including a gym and game room. Enjoy garage parking, Wi-Fi, and proximity to trails, Winter Park Village, and the gondola. Relax and recharge after every mountain adventure!

Guest favourite
A cozy living area features a green sofa and a striped armchair. A wooden dining table and chairs are positioned nearby, with pendant lighting above. The kitchen showcases stainless steel appliances and warm cabinetry, enhancing the inviting space.
Apartment in Winter Park
4.9 out of 5 average rating, 299 reviews

One Bedroom Condo - Winter Park Resort Base Area

Hit the slopes early on a powder day! If you need to pop back for a quick lunch, our condo’s convenient location makes it perfect for families. After an adventure-filled day, unwind in the oversized hot tub! As a spacious corner unit, this condo offers more room than standard 1-bedrooms. You’ll sleep comfortably on the king-size Tempurpedic bed, and the living room sofa easily converts into a queen pull-out bed for extra guests. Winter Park Short-Term Rental Registration No. [004361}

Top guest favourite
The image captures a scenic view of a mountain resort village, featuring multiple buildings and a ski slope in the background. Snow-covered trees line the pathway, while outdoor seating with umbrellas is visible in the foreground, inviting relaxation in the crisp mountain air.
Apartment in Winter Park
4.9 out of 5 average rating, 245 reviews

Ski-In Ski-Out Zephyr Mtn Lodge Condo w/ Hot Tub

Enjoy your stay right next to the Gondola here at the Zephyr Mountain Lodge - Winter Park Resort's premier ski-in/ski-out base lodging. This 1-bedroom, 1-bathroom condo is ideal for a small family or couple seeking mountainside convenience and complimentary amenities. Enjoy a direct ski-in/ski-out location, where winter adventures and summer endeavors are easily in reach! End each day with ease - whether you're soaking in the community hot tub or warming up by the unit’s fireplace.

Guest favourite
Apartment in Winter Park
5 out of 5 average rating, 18 reviews

Slopeside paradise in WP village

Welcome to ski-in-ski-out paradise at Winter Paradiso! Nestled in the heart of the action in Winter Park base village and mere steps from the Gondola, this 1BR/1BA condo in Zephyr Mountain Lodge has everything that a family or couple could want for a ski or mountain getaway! Featuring expansive views of Parry Peak and Mary Jane, free Wifi, full kitchen, one king bed and a sofa sleeper, multiple shared hot tubs, shared exercise room, heated underground parking and elevator access.

Top guest favourite
A spacious living room is highlighted by large floor-to-ceiling windows that frame expansive mountain views. A cozy mid-century sectional sofa is positioned on a light-colored area rug, with natural light enhancing the inviting atmosphere. A glimpse of the kitchen is visible in the background.
Apartment in Winter Park
4.97 out of 5 average rating, 111 reviews

Luxury Ski-In/Out | Ski to Winter Park Resort

Elevate your getaway in this cozy mountain condo, wrapped in mid-century charm and breathtaking views. Enjoy the mini Pub, snuggle up by the fireplace, or take in the mountain views. Sleep in luxurious comfort, and dine with a ski lift mural as your photo-worthy backdrop. Put a vintage record on, host a game night marathon, or soak in the infinity-style hot tub. The slope is located directly behind the building and you can walk or ski to the Winter Park Resort village center.

Guest favourite
A cozy living area features a brown sofa adorned with decorative pillows and a striped armchair near a window. A dining space with wooden chairs and a table is visible, while a snowy outdoor view includes a bridge decorated with a festive wreath.
Flat in Winter Park
4.96 out of 5 average rating, 137 reviews

Amazing Condo at the Base of Winter Park Resort

Our home at the base of the Winter Park Resort (100 meters from the Gondola) is updated (paint, furniture, lighting, bedding, kitchen supplies), clean, and modern to provide a cozy and comfortable base for every mountain activity: Ski, bike, play, hike, relax, and renew with a hot tub only 2 meters away. King bed, comfortable queen sleeper and a port-a-crib if you need it make this great for a family/group retreat. Winter Park Short-Term Rental Registration No. 4328

Guest favourite
The exterior of the condo complex is visible, showcasing multiple levels adorned with windows. Snow blankets the landscape, while a heated outdoor area features seating and a hot tub. Mountain views provide a scenic backdrop, emphasizing the peaceful surroundings.
Apartment in Winter Park
4.87 out of 5 average rating, 195 reviews

One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit

Located in the Winter Park Village, walking distance to The Gondola this condo has it all! The bedroom features a King bed with a memory foam pull out Queen in the living area. Complete Kitchen, full size fridge, dishwasher, large bathroom, and private covered patio with views of the Mountain. Walking distance to shopping, restaurants, & activities! One of only a handful of units with direct outdoor access. UPDATE: New hot tub is OPEN! Permit #009238

Guest favourite
An outdoor heated pool is featured alongside two hot tubs, surrounded by a scenic landscape of snow-covered trees and mountains. The area is paved with a spacious deck for relaxation, with clear skies above enhancing the serene atmosphere of the retreat.
Apartment in Winter Park
4.93 out of 5 average rating, 183 reviews

Ski-in/Ski-out, Luxury amenities +Free parking

Discover the perfect mountain retreat! Enjoy seamless ski-in/ski-out access, a first-floor location, and unwind in the indoor/outdoor heated pool and new hot tubs. Stay fit in our on-site fitness center, park hassle-free, and explore with a free local shuttle at your doorstep. With custom queen and bunk murphy beds, this cozy escape offers comfort and convenience. Your mountain getaway awaits – embrace the charm, relax, and make unforgettable memories!

Guest favourite
The living area features a comfortable sofa and armchair, centered around a coffee table. A round dining table with four chairs sits in view of a kitchen bar with pendant lighting. Natural light enters through large windows, enhancing the cozy atmosphere.
Apartment in Winter Park
4.96 out of 5 average rating, 135 reviews

Top floor, larger 1 bedroom in Winter Park Village

Conveniently located in the Winter Park Village at Fraser Crossing, this updated and oversized 1 bedroom condo sleeps 4 comfortably with a FULL KITCHEN!!! Enjoy the views that come with this peaceful and conveniently located penthouse unit. Close to entertainment, activities, restaurants, ice skating rink, and adventure! Most importantly, a short 2 minute walk to the Gondola...park your car and forget about it.

Guest favourite
The living area features a spacious sofa adorned with patterned pillows, and a coffee table sits on a patterned rug. Large windows allow natural light to fill the room, offering views of the surrounding mountains. A fireplace is positioned beneath the mounted television.
Apartment in Winter Park
4.88 out of 5 average rating, 321 reviews

Oversized 1bed Ski In/Out MTN VIEWS King&Qn beds

Oversized 1 bed in Zephyr Lodge, WP's only ski in/out condos. 20% larger than other 1 Beds w/ views of the mtn slopes & village. King bed in Bedroom + queen murphey in living room. Amenities: Window AC unit, ground level ski locker, outdoor hot tubs & fitness center. One Private underground parking for guests (summer free/winter $30 /day). Near starbucks, ski rental, shops, & restaurants!

Popular amenities for ski-in/out rentals near Winter Park Resort

Quick stats about ski-in/out rentals near Winter Park Resort

  • Total holiday rentals

    Explore 360 holiday rentals in Winter Park Resort

  • Nightly prices starting at

    Winter Park Resort holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 8,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    210 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    360 of Winter Park Resort holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Park Resort rentals

  • 4.8 Average rating

    Winter Park Resort stays are highly rated by guests – averaging 4.8 out of 5!