Family-friendly holiday rentals in Winter Park

4.98 out of 5 average rating, 129 reviews

A private hot tub is located on the patio, providing views of the living space through large glass doors. The interior features an open layout with a cozy fireplace and a TV visible on the wall. Modern furnishings create a welcoming environment.

Townhouse in Winter park

Modern Cabin w/ Hot Tub & Garage - Minutes to Mtn

2BR townhome with a loft in a woodsy neighborhood in Winter Park/Fraser. Want a relaxing scenic place to sit by the fire or enjoy Grand County's outdoor adventures? Come stay and enjoy this townhome with access to free shuttle transportation during the winter. Both bedrooms include King beds. The loft includes a daybed that expands to a king bed and the sofa pulls out to a bed. PRIVATE 7 PERSON HOT TUB on patio. Propane Grill, easy access to hiking/biking trails, restaurants, stores, bars, etc.

A circular hot tub is positioned within a fenced area, surrounded by snow-covered ground. The three-story building, featuring a mix of stone and siding, stands in the background under a clear blue sky. Balconies and sliding glass doors are visible on the structure.

4.95 out of 5 average rating, 150 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!

4.96 out of 5 average rating, 275 reviews

The modern mountain home is showcased against a backdrop of snow-covered terrain and distant mountain peaks. Its angled roof and contemporary design blend seamlessly with the natural surroundings. Large windows reflect the serene landscape, while surrounding trees add to the tranquil winter setting.

Cabin in Grand County

Scandinavian-Inspired Escape: Modern Cabin w/ Spa

Escape to our Modern Mountain Home in Grand County, Colorado, where luxury meets wilderness! Nestled amidst majestic mountains, this Scandinavian-inspired retreat offers the perfect blend of rustic charm and contemporary comfort. Wake up to breathtaking views, with hiking, biking, and skiing right outside your door. Highlights: • Panoramic mountain views • Close to Winter Park & RMNP • Scandinavian-inspired design • Wood-burning fireplace • Private hot tub Grand County Permit #106884

4.98 out of 5 average rating, 102 reviews

A modern stand-alone unit features a covered cedar deck with two dark wooden chairs facing an inviting entryway. Pathways lead through landscaped areas, with grassy surroundings and trees partially framing the view. An outdoor sauna is visible in the background.

Home in Fraser

Modern Downtown Home w/ Private Sauna on Bus Line

Enjoy a sanctuary in the heart of charming downtown Fraser—complete with a private outdoor sauna! Tucked among aspens yet just steps from the Fraser train/bus station, this modern home offers a rare blend of seclusion, convenience, and character (the train rumbles by across the street). Leave your car at home and enjoy restaurants, bars, coffee, grocery, and frequent transit to Winter Park all within an easy walk. Stocked with everything you need to feel at home, it’s the perfect basecamp.

4.97 out of 5 average rating, 482 reviews

A welcoming outdoor entryway features a covered porch with colorful hanging flower baskets. Two chairs are positioned next to a small table, inviting relaxation. A decorative rug adorns the area, complementing the wooden structure and surrounding greenery.

Guest suite in Fraser

Madge’s Studio Pets welcome!

Whether it be play time or quiet time (or both!), we offer our guests (and pets) the comfort of a large studio and yard at the end of a dead end street. You have a beautiful mountain setting with easy access to all your favorite summer activities. In addition, we are 45 minutes from Rocky Mountain National Park and the lakes of Grand Lake. After enjoying a perfect Colorado day, come back to your spacious room for a drink on your private patio to think about what restaurant to enjoy.

A modern living area is highlighted by a comfortable sectional sofa and a square glass coffee table. Floor-to-ceiling windows showcase scenic mountain views, while bright light fills the room. The open layout includes a sleek television mounted on the wall and a glimpse of the dining area.

4.97 out of 5 average rating, 106 reviews

Luxury Winter Park Studio*PrivHotTub*Majestic View

Brand New Studio styled in HIP MOUNTAIN CONTEMPORARY in EXCLUSIVE Leland Creek! Perched amongst the aspen trees with spectacular sunset views,you'll never want to leave your own private Hot Tub and Deck!Floor to ceiling windows with stunning mountain views,Room+Board furniture and rustic ski vibe fill the home with a Contemporary Chic style.Private Entrance.Good Pets are welcome.10miles to Granby.18 miles to Grand Lake+Rocky Mountain National Park.DenverInternational airport 1.5 HR.

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.

4.9 out of 5 average rating, 263 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.

4.95 out of 5 average rating, 165 reviews

Home in Fraser

Cozy Cabin Retreat • Hot Tub, Fireplace, Views

Beautiful, spacious, and cozy cabin perfectly located for year-round mountain adventures. Minutes from Winter Park Ski Resort, downtown Winter Park, and Fraser, and under an hour to Rocky Mountain National Park and Grand Lake. Enjoy stunning Byers Peak views from the patio, with easy access to hiking, biking, and Nordic ski trails. Comfortably accommodating multiple adults or two families, this home offers all-season access to Grand County’s outdoor recreation and scenic beauty.

4.94 out of 5 average rating, 163 reviews

A spacious living area features large windows that provide views of the mountains and natural light. Comfortable leather seating surrounds a low coffee table, with a decorative area rug enhancing the space. A warm ambiance is created by a nearby lamp and wooden elements.

Townhouse in Winter Park

Winter Park Townhome w/ Stunning Slope Views!

Your next Winter Park escape awaits at this stunning 3-bedroom, 2.5-bath vacation rental townhome - directly across from Winter Park Resort with amazing views of the slopes. Your group of up to 8 guests will love returning to the comfort of this home, offering over 1,800 square feet of living space. With such easy access to the slopes, trails, breweries, concerts and more, this is the perfect home base! Winter Park Short-Term Rental Registration No. 005732

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, 209 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

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.

4.89 out of 5 average rating, 226 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.

A spacious living area features a comfortable leather sofa adorned with decorative pillows. A stone fireplace serves as a focal point, while large windows allow natural light. A workspace is visible alongside a queen-size bed with a rustic plaid bedspread, creating a welcoming atmosphere.

5 out of 5 average rating, 108 reviews

Cozy Winter Park Riverfront Studio~ Walk Downtown

Riverside Rendezvous is a stylish studio nestled right on the Fraser River. This tranquil location is walkable to all the amenities one would desire in town. You will have a queen-size bed, queen-size sofa sleeper, full kitchen, bathroom, fireplace, private patio & ski closet. Walk to ski shuttle stop, miles of hiking/biking trails, fishing, restaurants, grocery store, bars, breweries & nightlife.

Popular amenities for Winter Park family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 195 reviews

The exterior of a spacious mountain home is framed by tall pine trees and blooming wildflowers. Large windows and a welcoming deck area are visible, suggesting an inviting atmosphere for outdoor relaxation. The building showcases a traditional design with a warm wood aesthetic.

Cabin in Granby

Private Luxury Mountain Log Home with Hot Tub

A cozy sitting area features a stone fireplace, framed by a wooden mantel. A smart TV is mounted on the wall opposite a gray sofa adorned with red cushions. A small coffee table sits on a patterned rug, complementing the warm ambience of the space.

4.97 out of 5 average rating, 66 reviews

Ski-in Ski-out Cozy Condo

4.95 out of 5 average rating, 66 reviews

The home is surrounded by tall trees, showcasing its unique architectural design with multiple levels and a circular section. A spacious outdoor area can be seen, complementing the natural landscape. Various outdoor features, including decks, are visible amidst the greenery.

Cabin in Fraser

Cosmic Cabin: Views, Trails, HotTub by Winter Park

5 out of 5 average rating, 63 reviews

A hot tub is positioned on a private deck, featuring bubbling water and colorful lights. The view extends to rolling mountains under a partly cloudy sky, with green landscaping visible in the foreground. A railing outlines the deck, providing an unobstructed perspective of the surroundings.

Townhouse in Fraser

New Condo: Large Hot Tub & Views

5 out of 5 average rating, 11 reviews

The Coop: Ski In/Ski Out Studio - Winter Park

5 out of 5 average rating, 14 reviews

New 1 bedroom, downtown, mt views and private HT

4.9 out of 5 average rating, 230 reviews

The living area features a spacious leather sectional sofa arranged around a coffee table, creating an inviting space. A stone fireplace serves as a focal point, while large windows allow natural light to fill the room. A television is positioned within a wooden console.

Townhouse in Winter Park

Beautiful Townhome in Downtown Winter Park!

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, 250 reviews

Homebase Snowblaze

Family- and pet-friendly home rentals

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, 164 reviews

Hideaway Park! Hot tub,Pool,FitnessCtr&FreePrkg

Guest suite in Winter Park

4.99 out of 5 average rating, 137 reviews

Creekside guest suite with hot tub & fireplace

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, 196 reviews

Great Condo right on the Creek License #005702

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.

4.96 out of 5 average rating, 136 reviews

Calm vibes and a great view at the Alpen Rose

4.94 out of 5 average rating, 106 reviews

A spacious living room features large windows allowing natural light to fill the area. Comfortable seating arrangements include a sectional sofa and an accent chair, complemented by a round coffee table. A well-equipped kitchen is visible in the background, creating a harmonious open-concept design.

Holiday home in Granby

Modern Mountain Golf/Ski/Lake Retreat with Hot Tub

4.92 out of 5 average rating, 179 reviews

The exterior of the log cabin is showcased against a clear blue sky, surrounded by vibrant autumn foliage. A gravel driveway leads to the entrance, while a spacious yard reflects the natural beauty of the mountain landscape, adorned with tall trees and colorful foliage.

Cabin in Tabernash

Cozy Log Cabin Getaway ~ 20 Min to Winter Park

4.98 out of 5 average rating, 119 reviews

Cabin in Tabernash

Private Zen Retreat for Couples in Devil’s Thumb

4.95 out of 5 average rating, 170 reviews

Cabin in Granby

Charming 3BR Riverfront Cabin - Pet Friendly

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 118 reviews

The cabin's exterior is showcased, featuring multiple levels and a spacious deck. A large flat stone patio includes several seating options. Nearby, the landscape is landscaped with gravel and grass, surrounded by a community of similar structures.

Cabin in Granby

Cozy Cabin on the Fraser River

4.86 out of 5 average rating, 239 reviews

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.

Condo in Fraser

Beautiful Condo with Pool, Hot Tub and Rec Room

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, 149 reviews

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

4.88 out of 5 average rating, 426 reviews

A cozy seating area features a dark sofa adorned with soft pillows, positioned beside large windows with yellow curtains. A wooden coffee table is set with a plate of fruit and a book, while a warm light fixture hangs overhead, enhancing the inviting ambiance.

Condo in Granby

Cozy Studio~Mtn Views~Salt Water Pool & Hot-Tubs

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, 116 reviews

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

A cozy living space is highlighted by a large sectional sofa positioned against a brick fireplace. Natural light fills the room through a skylight and glass door that opens to a private deck. A desk with a chair adds a functional touch to the layout.

4.95 out of 5 average rating, 155 reviews

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

A balcony view overlooks a lush green area with a picnic table situated beside a gently flowing river. Towering trees provide shade, while shrubs line the water's edge, creating a serene outdoor space that invites relaxation.

4.92 out of 5 average rating, 143 reviews

Winter Park Riverside Retreat WP ST Reg#005544

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.