Apartment holiday rentals in Winter Park

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Top-rated apartment rentals in Winter Park

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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, 25 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
An inviting living area features a mix of seating options, including a spacious couch and a rocking chair. A coffee table centers the space, while a kitchen bar with stools offers additional seating. Decorative artwork and a guitar adorn the walls, contributing to a cozy ambiance.
Flat in Winter Park
4.82 out of 5 average rating, 112 reviews

Cozy Condo on the Fraser River

Bright airy western sunset view with no obstructions looking down on Fraser river 25' in front of building. Walking distance to all of Winter Park. One year old new Rec Center with pool, hot tubs, pool table, Computer, guitar, great locker rooms with showers. Free town bus comes by hourly and pick up is right at our building. Car not really needed once your here. Winter Park is great Skiing with all the summertime activities as well. Sorry we are not pet friendly. We just installed a new stove.

Top guest favourite
A modern kitchen space is highlighted by a central island with seating for four. Sleek cabinetry in soft colors complements stainless steel appliances, including a refrigerator and a range hood. Pendant lights provide illumination above the island, enhancing the inviting atmosphere.
Flat in Winter Park
4.95 out of 5 average rating, 132 reviews

Tipsy Fox @ Downtown Winter Park Near the Slopes!

Welcome to the perfect Winter Park getaway! Located in downtown, this cozy one-bed, one-bath condo is just steps away from Hideaway Park and its year-round free events. With 3 queen beds, including a sleeper sofa and a Murphy bed, it comfortably sleeps 6 guests. Enjoy the heated garage and ski locker for your vehicle and snow gear. After outdoor activities, unwind in the hot tub, gather around the fire-pit, or relax on the balcony. Conveniently close to food, slopes, tubing hill, and amenities!

Top guest favourite
The exterior of Snowblaze Condominiums is visible, showcasing a multi-story building with a modern design. Stone pillars line the entrance, and large windows allow natural light to illuminate the entryway. Surrounding pine trees add to the mountain setting.
Flat in Winter Park
4.93 out of 5 average rating, 126 reviews

Sleeper@SnowBlaze! Great Location! Hot Tubs/Pool!

Town of Winter Park license (007884) Newly renovated studio in Snowblaze Condominiums! Perfect location in the Town of Winter Park, close to Winter Park Resort and bus stop outside the front door, and walking distance from all the shops, restaurants, and bars in town! Super comfy Queen size bed in a large studio apartment, large couch and ottoman with huge TV! Updated amenities for the community! Pool has been refinished, new outdoor fire pit area, access to gym and community areas included.

Guest favourite
A spacious studio is depicted, featuring a comfortable sofa paired with a small round table. Large windows allow natural light to fill the space, while a cozy bed is positioned against a wall. A television is mounted opposite, enhancing the functional layout.
Flat in Winter Park
4.84 out of 5 average rating, 88 reviews

Studio Downtown Winter Park

Pet-friendly. Do NOT book if you have pet allergies. On the bus route to the resort and within a 3-minute walk to Cooper Creek shopping and restaurants, Hideaway Park and the Visitor's Center. Our well-appointed studio sleeps 4 comfortably and has amazing amenities including 2 hot tubs, a heated lap pool, an outdoor fire pit. There is a complimentary parking space in the covered garage, along with a secure ski locker to store your gear at the end of a long day. STR License #021860

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
A well-lit common room features large windows with views of surrounding trees. Cozy seating arrangements include a comfortable sofa and two armchairs. A dining area with wooden chairs and a table is present. A television is located on a shelf beside a small bookshelf.
Flat in Winter Park
4.79 out of 5 average rating, 130 reviews

The Alpen Rose- Cozy cabin feel w/amazing Views

Planning a mountain getaway? The Alpen Rose is your perfect home base. Tucked among aspen trees in downtown WP, this warm and welcoming retreat offers the ideal blend of comfort, convenience, and mountain feels (not to mention VIEWS). Start your day with stunning views of the Continental Divide and WP Resort, then wind down with your crew by the fireplace as the alpenglow lights up the sky. Alpen Rose is the ideal spot to relax and reconnect and aspen peep.

Superhost
A modern building with three stories is shown against a clear blue sky. The exterior features a mix of wood and stone elements with large glass windows. Balconies extend from the second and third floors, and snow is visible on the ground.
Flat in Winter Park
4.75 out of 5 average rating, 24 reviews

Ski-in/Ski-out Winter Park Studio

Check out the AlpenGlow on the Continental Divide from this newly constructed (2023) studio with large sitting area. The studio is situated steps away from the Corridor Trail that will take you to the Gondola at the base of Winter Park. The kitchenette has a refrigerator, microwave, and coffee maker. Enjoy the soaking tub and awesome hot tub, free laundry facility, and fitness area. You’ll feel right at home having aprés after an epic day on the slopes.

Top guest favourite
A bright living space features a light-colored sofa positioned near a large window, showcasing views of the outdoors. The walls are adorned with warm wood paneling, while a minimalist table sits in front of the sofa. Natural light enhances the cozy atmosphere.
Flat in Winter Park
4.95 out of 5 average rating, 128 reviews

Calm vibes and a great view at the Alpen Rose

Currently available for weekly and longer rentals. Will review any other requests. Welcome! I'm sharing with you my home away from home. A stay here comes with wonderful views of the Continental Divide and Winter Park Resort. The Lyft (free bus) stops just a few steps from the house. Cook with a view and fully stocked kitchen. The living space has a comfy sofa and wood-burning stove. Molekule air filters & Dyson fan to keep you comfortable.

Guest favourite
A modern living area is featured with high ceilings and wooden beams. An open kitchen includes stainless steel appliances and warm wood cabinetry. A comfortable sectional sofa in navy blue faces a wooden coffee table, with a light rug anchoring the space. Large windows frame a view of the surrounding mountains.
Flat in Martin Acres
4.97 out of 5 average rating, 144 reviews

“Blue Owl” - Tree House Views! Couples Getaway!

Blue Owl offers spectacular tree house vibes with a view of Mt Evans. Includes 1 bed / 1 bath / 1 bonus “loft” bedroom providing the perfect escape for 1-4 people Approximately 11,000-ft above sea level. Is accessed via a scenic 20 minutes drive from I-70, along Fall River Road. Walkable to the trailhead for St Mary’s Glacier, a 1.9-mile well-used trail to a beautiful lake. Includes parking. *4WD required during winter months.*

Guest favourite
The lobby features a modern design, with two comfortable sofas positioned around a rustic coffee table. A stone fireplace is centrally located beneath a wall-mounted television. Natural light flows through large windows, and a tastefully decorated Christmas tree adds a festive touch.
Flat in Winter Park
4.95 out of 5 average rating, 243 reviews

Founder’s Pointe Ski/In Out #4467

NO PETS FREE SUMMER PARKING SKI SEASON PARKING $24 per day ****Monthly rentals ski season = free parking**** 28 days or more, no exceptions Remodeled Winter Park resort studio - FOUNDER'S POINTE BUILDING. Easy 5 min drive to downtown. Free shuttle (to 2am) NEW HOT TUB Open 9am-9pm *Must be 25 to book*

Guest favourite
An outdoor swimming pool is surrounded by a stone patio, featuring fountains that create gentle splashes. The backdrop includes a snow-covered hill and mountain trees, with nearby buildings displaying various architectural styles. Lounge chairs are arranged along the edge of the pool.
Flat in Winter Park
4.86 out of 5 average rating, 304 reviews

Village of Winter Park Condo

Contemporary vacation rental is located at the base of the winter park ski resort. Premier one bedroom with king bed. Sleeps 4. On third floor with access to bbq, BRAND NEW hot tub and fireplace. Enjoy an efficiency kitchen with stainless steel appliances. Self check in. License #005596

Popular amenities for Winter Park apartment rentals

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$305 SGD$292 SGD$287 SGD$190 SGD$162 SGD$180 SGD$195 SGD$184 SGD$165 SGD$145 SGD$179 SGD$291 SGD
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Quick stats about flat rentals in Winter Park

  • Total holiday rentals

    Explore 130 holiday rentals in Winter Park

  • Nightly prices starting at

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

  • Verified guest reviews

    Over 4,030 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    130 of Winter Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Park rentals

  • 4.9 Average rating

    Winter Park stays are highly rated by guests – averaging 4.9 out of 5!

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