Condo vacation rentals in Winter Park

A heated outdoor pool is framed by a wooden clubhouse, with several lounge chairs positioned around the pool area. The clear blue water reflects the sky, and trees with budding leaves line the perimeter, adding a touch of greenery.

4.92 out of 5 average rating, 165 reviews

Hideaway Park! Hot tub,Pool,FitnessCtr&FreePrkg

BEST Location in Winter Park!!Trailhead condos offer a year-round heated pool, hot tub, fire pit, patio, clubhouse, large indoor lounge, fitness room & game room. Just steps to Fraser River trail, restaurants, shopping and free ski shuttle. *On Hideaway Park* Access to Summer concerts&festivals, playground, picnic area, fire pit, and skate park to entertain kids! Relax by the fire or private furnished covered deck. Top floor (w/elevator) corner unit w/views! Pets welcome! (w/add'l clean fee).

A modern building is set against a mountainous backdrop, featuring large windows that bring in natural light. A spacious deck surrounds a hot tub, with clean lines and a mixture of colors in the exterior design. A grassy area leads to a stony path.

4.94 out of 5 average rating, 156 reviews

Cozy mountain retreat in downtown Winter Park

Lovingly remodeled Hi Country Haus 1 bedroom 1 bathroom condo central to downtown Winter Park. Use our Tiny Mountain Retreat as a launchpad to all the local access Winter Park has to offer or as a space for rejuvenation in this beautiful mountain town. Incredible access to local trail running, mountain biking, backpacking, fly-fishing, hiking and skiing. Grand Lake and Rocky Mountain National Park are easily and often visited from our spot as well. WP Short-term rental registration #019404

4.93 out of 5 average rating, 279 reviews

Top Floor Condo Steps From Free Shuttle w/Hot Tub

Two bedroom, Two bath, top floor condo with three private balconies. Our fully equipped kitchen comes complete with all the amenities you need to prepare your favorite meals, and we provide complimentary toiletries for your convenience. 15 minute walk to main street bars and restaurants and on the free ski shuttle line to the Mountain or Main Street. Take advantage of our free parking in front of the building and unwind after a long day on the slopes or trails in the community outdoor hot tub.

A modern kitchen features clean white cabinetry and a spacious island equipped with seating for four. Natural light illuminates the space, highlighting the sleek countertops and organized open shelving. Essential appliances, including a refrigerator, are positioned for convenience.

4.88 out of 5 average rating, 251 reviews

Homebase Snowblaze

Enjoy the magic of the Fraser River Valley and charm of downtown Winter Park from our well-equipped, completely remodeled studio. Only an hour and thirty minute drive from Denver International Airport. Walking distance to Winter Park's Main St. lined with shops and dining and a quick 5 minute drive to the world class slopes of Winter Park resort. Take advantage of the free "Lift" bus, with a stop right out front of the building and a ride to the resort in less than 5 minutes. WP STR # 009036.

A peaceful outdoor view showcases still waters bordered by lush greenery and distant mountains under a bright blue sky. Bicycles are parked on the balcony, emphasizing accessibility to outdoor activities and trails nearby.

4.97 out of 5 average rating, 134 reviews

Walk to Restaurants! Fraser Bike Park is Open!

June is almost booked! Don't miss out on July! Bike, hike and fish from the front door! Don’t miss this spacious 1 BR Fraser condo perfectly located for your spring and summer adventures in Grand County. You are just a short walk from the grocery store, restaurants, breweries and the Fraser River and Trail. You are a .8 mile walk from the train station which offers daily Amtrak service and weekend Ski train service in the winter. You are also steps away from the free Lift shuttle service.

A hot tub is situated on a wooden deck, releasing steam into the crisp winter air. Snow blankets the ground, with towering evergreen trees visible in the background. A covered pavilion can be seen in the distance, framed by the sunlight filtering through the trees.

4.95 out of 5 average rating, 155 reviews

Walk to Town, Front Door Ski Shuttle Pick-up!

Located in the heart of Winter Park, this stylish top floor condo is a 2 bedroom 2 bath that's perfectly situated to meet all your vacation needs. Convenient front door ski shuttle pickup/drop-off! The condo is tucked away on a beautiful hillside, allowing for privacy and panoramic views, only a couple of blocks away from restaurants/bars. It includes two queen size beds, a sofa sleeper, fully-stocked kitchen, wood-burning fire place, spacious private patio, skylights, and new furniture.

A cozy living area features a brown leather sofa paired with two white armchairs arranged around a wooden coffee table. A decorative bear print adorns the wall, and the space is illuminated by warm lighting. The open kitchen is visible in the background.

4.85 out of 5 average rating, 112 reviews

Prime location, amazing views, stylish, sleeps 7

Relax and unwind at this stylish, centrally-located condo. Features include an updated kitchen as well as both bathrooms, a cozy fire place, spacious patio to enjoy morning coffee with incredible views all season. Located just 0.5 miles from downtown Winter Park you can easily walk to restaurants and shops. A shuttle stop to Winter Park Resort is conveniently located just outside the front door making the slopes just minutes away. Easy access to biking/hiking trails as well as Wolf Park.

4.86 out of 5 average rating, 117 reviews

Mountain Getaway Condo w/ Pool and Hot Tub

Freshly Updated- 2 Bedroom, 1 Bath Meadow Ridge Condo with space for the whole family or your favorite group to enjoy a mountain getaway! Located right on the FREE “Lift”bus/shuttle route to Winter Park Ski Resort, adventure awaits in every direction from this perfectly located condo. Start hiking or biking right out the front door. Guests have access to all the amenities at Club MeadowRidge, located steps away from the condo. Stay, Play, Relax at our wonderful Mountain Getaway!

A community pool area features a clear blue water pool surrounded by a sun deck. Several lounge chairs are positioned alongside the pool, with a wooden clubhouse visible in the background, providing a spacious area for relaxation and gatherings.

4.87 out of 5 average rating, 106 reviews

Four-Season Winter Park Condo w/ Pool Access!

Seasonal recreation on world-class mountain trails awaits at this Winter Park vacation rental! Located in the Trailhead Lodges community - under a half-mile to the closest ski shuttle - this 2-bedroom, 2-bath condo offers all the at-home comforts in a premier mountain destination. Work remotely with beautiful views while also enjoying easy access to countless year-round outdoor activities for the whole group. You’ll also have access to a community pool, hot tub, clubhouse, and more!

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.

4.87 out of 5 average rating, 211 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

An open kitchen space features wooden cabinetry and granite countertops. A large island with seating for six is highlighted at the center, while stainless-steel appliances and a scenic nature photograph decorate the walls. The area is well-lit with overhead lighting.

4.96 out of 5 average rating, 104 reviews

The Best Location in Downtown Winter Park!

Escape to the mountains in this beautifully renovated two-story condo, ideally located in the heart of downtown Winter Park. Cozy up by the fireplace, relax in the hot tubs, or enjoy the breathtaking mountain views from your private balcony. With shops, restaurants, bars, and live events just steps away, plus a nearby bus stop offering a quick five-minute ride to Winter Park Resort, adventure and convenience are at your doorstep. STR License #018230

A spacious lobby area features two light-colored sofas arranged around a coffee table, with a modern fireplace set against a textured wall. Large windows allow natural light to fill the space, while a wall-mounted TV provides entertainment options. The flooring is a warm wood tone, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 229 reviews

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

Leone’s Den | A Boutique Mountain Retreat at the Base of Winter Park Resort Step into refined alpine comfort at Leone’s Den, an elegant studio just steps from the slopes. Located across from the Village Base, enjoy easy access to dining, shopping, and après-ski, then retreat to a warm space with a cozy fireplace and elevated finishes. Relax in Winter Park’s largest hot tub and return to plush linens and beautiful mountain and village views.

Popular amenities for Winter Park condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.77 out of 5 average rating, 56 reviews

Selak Luxury

A private hot tub is positioned on a deck, surrounded by a stone-clad exterior. Lounge seating is arranged nearby, with outdoor string lights providing illumination. Large windows reveal a mountain backdrop, while a covered area offers a dining setup adjacent to the hot tub.

5 out of 5 average rating, 65 reviews

Bonus Bunk Room! Hot Tub/Walk2 Restaurants/Brewery

A spacious living area features modern furnishings, including a cozy sofa and a stylish dining table. Natural light streams through large sliding glass doors that lead to the private deck. A well-equipped kitchen with sleek appliances is positioned adjacent, enhancing the inviting atmosphere.

5 out of 5 average rating, 45 reviews

Fresh Modern Mountain Getaway | Views + Garage

5 out of 5 average rating, 22 reviews

Luxury Condo w Private Hot Tub - Fraser, CO

5 out of 5 average rating, 65 reviews

The Rustic Moose

The living room features a comfortable brown leather sofa paired with a light-colored armchair. A wooden coffee table sits on a soft area rug, and an electric fireplace is set into a modern stone wall. Large windows provide natural light and views of the mountains.

4.95 out of 5 average rating, 43 reviews

NEW | Lux Mountain Condo | Private Hot Tub

5 out of 5 average rating, 21 reviews

New Condo Downtown Winter Park-Close to the Slopes

A spacious living area features leather sofas arranged around an inviting fireplace. Two ottomans and a large television are positioned nearby, while natural light streams in through large windows adorned with wooden frames.

4.94 out of 5 average rating, 67 reviews

10 Minute Walk to the Winter Park Gondola 6 beds.

Pet-friendly condo rentals

4.91 out of 5 average rating, 317 reviews

The image features a serene lake scene reflecting surrounding mountains and trees in clear blue water. A three-story building is visible along the shore, complemented by vibrant greenery and a clear sky, creating a peaceful natural setting.

Condo in Idaho Springs

Blue Moose

A warm living area features a wood-burning fireplace framed by wooden paneling. A cozy rug is positioned in front, with a dog resting beside it. Above the fireplace, a framed artwork adds a decorative touch, while additional items are arranged on the mantle.

4.93 out of 5 average rating, 105 reviews

Cozy Mountain Getaway - Minutes to Winter Park

A serene snowy landscape showcases dense evergreen trees blanketed in fresh snow. The balcony railing is visible, providing a view of the winter scene. Soft light filters through the branches, creating a peaceful atmosphere in the surrounding nature.

4.75 out of 5 average rating, 197 reviews

Great Condo right on the Creek License #005702

Superhost

A sign indicating the various snow depth measurements at Winter Park is partially buried in snow, with visible markers at six-inch intervals up to 18 inches. The forest backdrop is lined with snow-covered trees, creating a peaceful winter scene.

4.77 out of 5 average rating, 287 reviews

Michael’s Dream Condo #15 Winter Park

A dining area showcases a table set for four, complemented by green placemats and glassware. A flat-screen TV is mounted on a wood-paneled wall, while a stone fireplace adds warmth to the space. A nature-themed artwork enhances the atmosphere.

4.88 out of 5 average rating, 561 reviews

Granby Mountain Retreat

4.91 out of 5 average rating, 143 reviews

Tall Timbers of the Rockies

4.81 out of 5 average rating, 377 reviews

Hotel-Style Queen Room Near RMNP | Pool & Hot Tubs

A comfortable living area features a large television mounted on the wall above a wooden entertainment unit. The unit contains books and decorative items. A clear view of the kitchen and dining area is visible in the background, along with modern appliances and a casual seating arrangement.

4.99 out of 5 average rating, 124 reviews

Winter Park Getaway for Mountain Biking/Hiking!

Condo rentals with a pool

Superhost

The exterior of the building showcases a four-story structure with a mix of red and stone finishes. Lush greenery surrounds a stone fire pit and seating area, while mountains are visible in the background under a partly cloudy sky.

4.82 out of 5 average rating, 150 reviews

Winter Park 2bd/2ba (Sleeps 6) - Ideal Location!

A spacious living area features a modern sectional sofa and a dark stone fireplace, creating a cozy focal point. A large flat-screen TV is mounted on the wall above the fireplace. Light filters in through the high ceilings, enhancing the open layout.

4.86 out of 5 average rating, 240 reviews

Beautiful Condo with Pool, Hot Tub and Rec Room

A cozy living room features a comfortable armchair with an ottoman, a wooden TV stand with decorative elements, and a fireplace set against a textured wood wall. Natural light filters through sheer curtains, highlighting a vintage artwork depicting Winter Park.

4.9 out of 5 average rating, 151 reviews

Cozy 2 bed/2 bath with Hot Tub and Mountain View

A modern kitchen setup features a granite countertop with bar seating for four. Stainless steel appliances, including a refrigerator and oven, complement the tile backsplash. A coffee maker is visible, along with pantry items organized on shelves.

4.91 out of 5 average rating, 320 reviews

On Fraser River - King bed - pool & hot tubs @ rec

The kitchen features rich wooden cabinets and granite countertops. An under-mount sink is positioned at the island, with a view of the stainless-steel stove and microwave. Stone accents add texture to the space, while shelves display decorative items and dishware.

4.95 out of 5 average rating, 117 reviews

Walk to town! Indoor pool, sauna, hot tubs.

A stone fireplace is centered in the room, flanked by a television mounted on the wall. A dining table with two red dishes sits in front of the fireplace, while a photo of a bear adorns the wall above. Warm tones create a cozy setting.

4.88 out of 5 average rating, 131 reviews

Bear's Den

4.98 out of 5 average rating, 139 reviews

Cozy Condo - 20 miles to RMNP w/ Hot Tub & Firepit

A scenic mountainous landscape is showcased, with snow-covered peaks under a clear blue sky. The foreground features a line of trees and a snow-blanketed ground, while distant mountains create a dramatic backdrop.