Condo holiday rentals in Winter Park

An open-concept living area presents a stone fireplace and vaulted wooden ceiling. A dining table with black chairs is positioned beside a fully equipped kitchen featuring stainless appliances and granite countertops. Natural light filters in through large windows, highlighting the cozy seating area.

4.91 out of 5 average rating, 175 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).

ValueFamilyPets

The welcoming living area showcases a spacious sectional sofa adorned with a colorful throw. A stone accent wall complements the large flat-screen smart TV. Natural light enters through expansive windows, illuminating the area, while a modern counter separates the kitchen from the living space.

4.94 out of 5 average rating, 161 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

LocationValueIndoor spaces

The fully equipped kitchen features wood cabinetry, modern appliances, and a large island with seating for four. A dining area with a circular table and four chairs is positioned nearby. Warm lighting is provided by a decorative pendant fixture, enhancing the cozy ambiance.

4.93 out of 5 average rating, 284 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.

ValueFamilyCleanliness

A modern studio is presented, featuring a well-equipped kitchen with bar stools at the counter. Two armchairs sit on a patterned area rug, and a spacious bed is visible in the foreground. The design incorporates neutral tones and textured wall tiles.

4.88 out of 5 average rating, 257 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.

ValueLocationCondition

A cozy living area features a stone fireplace with a flat-screen television mounted above. Natural light floods in through large windows, revealing scenic mountain views. Comfortable seating is provided by a brown sofa, complemented by a rustic wooden coffee table. Soft carpeting enhances the inviting feel.

4.9 out of 5 average rating, 147 reviews

Condo-City Center of Winter Park/Hot Tub/THE VIEWS

Amazing condo in the heart of Winter Park ★ Breathtaking Views of Winter Park Resort & The Continental Divide! ★ Quick 5 minute drive to ski slopes ★ In the heart of Winter Park ★ Walkable to town, shops, restaurants ★ Free parking ★ New stainless steel appliances ★ Cozy, Modern Furnishings, & Stylishly Decorated ★ 2 Bedrooms, Master has En-suite Bathroom ★ Fully-stocked kitchen for cooking ★ BBQ Grill & swing on Balcony ★ Fast Wifi & Cable TV/lots of channels ★ Hot Tub ★ 5 STARS!!!

FamilyLocationHospitality

A spacious living area is shown, featuring a large sectional couch adorned with various decorative pillows. A coffee table sits at its center, and two armchairs are positioned nearby. Natural light enters through sliding glass doors, providing a view of the outside snow-covered landscape.

4.85 out of 5 average rating, 252 reviews

Main Street Luxury - Hot Tub + Trails

You'll feel right at home at the hearth of this updated condo. You'll be on the slopes in 2 bus stops with pickup just outside. On Main Street, across from Cooper Creek and the Rendezvous Event Center, the town awaits. Host family style feasts with the fully equipped kitchen and dine up to nine. Relax in the hot tubs, on the huge couch by the big screen digital cable TV with streaming services, on the deck and in the hot tubs. Decadent Cal King bed in master. Ski lockers by the elevator.

ValueLocationHot tub

A modern dining area is highlighted by a round table surrounded by green chairs, with a decorative centerpiece. A stylish light fixture hangs above, and the open kitchen features stainless steel appliances and wooden cabinetry. Natural light filters through large windows, enhancing the inviting space.

4.95 out of 5 average rating, 112 reviews

New Build | Private Hot Tub | Mtn Views | Gameroom

Enjoy a wonderful, mountain retreat in Fraser when you visit this 2-bed, 2-bath vacation rental. Property includes a private hot tub, lock-off suite, fully equipped kitchen, heated garage/game-room, smart TVs, this condo has everything you'll need for a relaxing stay. Garage includes a tornado foosball table and Pop-a-shot with room to park a car. Prime location that is 2-minutes off of the main retail corridor for Winter Park and Fraser! Winter Park resort is a short 8-minute drive!

ValueFamilyCheckout

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, 144 reviews

Walk to Restaurants! Bring Your Fishing Pole!

Don’t miss the fall colors! Book now! Bike, hike and fish from the front door!! 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.

ValueLocationAccess

The open living area features modern furnishings with a large sectional couch and accent chairs. A stone fireplace is positioned beside a flat-screen TV. Natural light floods in through the glass doors that lead to a private balcony offering mountain views.

4.87 out of 5 average rating, 112 reviews

Hike & Bike! Mtn-View Condo 1 Block to Main St

Soak up the sun and enjoy alpine adventures at this 2-bed, 2-bath condo in Winter Park! Boasting a modern interior with all the comforts of home and community amenities like a hot tub and bike storage, this vacation rental ensures space for the whole crew! Grab a brew and bite to eat on Main Street, just a short walk away, or head out to conquer the mountain biking and hiking trails in the Rockies. After active days, cook dinner or host your own cookout on the patio!

LocationFamilyComfort

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.

4.9 out of 5 average rating, 241 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.

ValueLocationQuiet

The living area features a stone fireplace as its focal point, complemented by a cozy leather sofa and a vintage wooden coffee table. Large windows provide natural light, while a wall-mounted TV sits on a wooden console. A textured area rug adds warmth to the space.

4.98 out of 5 average rating, 430 reviews

Winter Park Studio: On the River~ Walk Downtown!

Fireside Haven is a cozy studio located on a secluded spot RIGHT on the Fraser River, yet is walkable to all that downtown Winter Park has to offer. Dine-out, shop, enjoy coffee at a café, cocktails at happy hour, hike/bike and catch the ski shuttle all within a five-minute walk from your front door! You will have a king-size bed, queen-size sofa sleeper, full kitchen, bathroom, fireplace, private patio & ski closet.

FamilyLocationOutdoor spaces

4.96 out of 5 average rating, 110 reviews

Downtown Mtn Oasis + Hot Tubs | Steps to Events

Escape to the mountains in this beautifully renovated 2-story condo in the heart of downtown Winter Park. Cozy up by the fireplace, relax in the hot tubs, or take in breathtaking views from your private balcony. Enjoy shops, dining, and live events just steps away, plus a free shuttle stop right nearby for a quick 5-minute ride to Winter Park Resort. Adventure and convenience are at your doorstep! STR License #018230

ValueLocationSleep quality

Popular amenities for Winter Park condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

An inviting family room features a spacious seating area with leather couches, complemented by natural light filtering through sheer curtains. A kitchen bar with three stools provides additional seating, while a large TV is positioned for easy viewing. Decorative artwork adds a touch of character to the space.

4.98 out of 5 average rating, 171 reviews

Updated Fraser Condo | Trails, Shuttle & W/D

LocationValueCondition

4.78 out of 5 average rating, 338 reviews

Walk to Gondola · Alpine Slide & Village

LocationFamilyCleanliness

A private balcony features a round table surrounded by four wicker chairs, offering expansive views of the Fraser Valley and mountains. Sunlight illuminates the area, and the nearby river reflects the clear sky.

4.98 out of 5 average rating, 329 reviews

View • Fireplace • Hot Tub • Sauna • Pool

LocationValueHospitality

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, 199 reviews

Great Condo right on the Creek License #005702

FamilyLocationQuiet

A welcoming living area features a stone fireplace with a modern fire display. A large sectional couch and coffee table are arranged around a colorful braided rug. A flat-screen TV is mounted on the wall, with a view of nature through the window. A cozy front door leads to the outside.

4.87 out of 5 average rating, 119 reviews

WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool

LocationFamilyCheckout

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.

4.91 out of 5 average rating, 275 reviews

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

LocationFamilyAir conditioning

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, 328 reviews

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

ValueLocationDecor

4.98 out of 5 average rating, 163 reviews

Modern 2BR Condo •Private Hot Tub•Near Winter Park

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Pet-friendly condo rentals

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

LocationValueParks

A private hot tub is set against a backdrop of snow-covered grounds and mountains. Rolled towels are neatly placed beside the tub. Scenic views of the outdoors are framed by a covered patio structure, adding to the tranquil atmosphere.

5 out of 5 average rating, 99 reviews

NEW+ Winter Park+ Hot Tub+ Garage+ Coffee bar

ValueFamilyParking

4.94 out of 5 average rating, 34 reviews

Trestle Bike Park•Hot Tub•Pet Friendly•Mtn View

ValueLocationBathroom

A spacious living area features a red seating arrangement with a comfortable sofa and armchair, complemented by light streaming through multiple windows. A kitchen island with a sink is visible, alongside a dining area that includes four chairs. A stone fireplace adds a touch of warmth to the space.

4.86 out of 5 average rating, 517 reviews

Cozy 1 bedroom Granby Ranch condo

ValueLocationHot tub

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.

4.86 out of 5 average rating, 117 reviews

Prime location, amazing views, stylish, sleeps 7

ValueLocationPets

4.91 out of 5 average rating, 146 reviews

Tall Timbers of the Rockies

LocationValueCheckout

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, 573 reviews

Granby Mountain Retreat

FamilyLocationWi-Fi

4.81 out of 5 average rating, 392 reviews

Queen Room | Pool & Hot Tubs | Near RMNP

FamilyValueLaundry

Condo rentals with a pool

A welcoming living area features a dark sofa adorned with decorative pillows. Two wide windows with wooden blinds frame serene views of the surrounding mountains, while a rustic wooden table complements the space. Soft natural light highlights the cozy interior.

4.72 out of 5 average rating, 297 reviews

Entire Condo In The Heart of Winter Park

FamilyValuePool

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, 152 reviews

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

LocationFamilyBiking

A panoramic view showcases the majestic mountains, framed by a landscape of rolling hills and dotted with trees. The seasonal colors reveal golden foliage alongside patches of green, while a serene sky provides a dramatic backdrop with soft, cloud-covered tones.

4.9 out of 5 average rating, 152 reviews

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

FamilyValueParking

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.

4.93 out of 5 average rating, 120 reviews

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

ValueLocationAmenities

A spacious bedroom is furnished with a wooden king bed, layered with a white comforter and a brown throw. Two bedside tables with lamps flank the bed. A colorful autumn-themed artwork adorns the wall above, complementing the warm tones of the decor.

4.95 out of 5 average rating, 129 reviews

Mountain Delight Near Winter Park

LocationValueCheckout

4.98 out of 5 average rating, 151 reviews

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

FamilyValueWalkability

An indoor swimming pool is surrounded by large windows that allow natural light to fill the space. The clear water reflects the overhead beams and sunlight, while lounge chairs are positioned nearby for relaxation.

4.77 out of 5 average rating, 152 reviews

Perfect ski Condo

FamilyLocationCleanliness

A modern living space is showcased, featuring two dark leather sofas with decorative pillows, a coffee table, and a simple area rug. The kitchen area includes white cabinets, stainless steel appliances, and a small wood island, all illuminated by recessed lighting.