Family-friendly holiday rentals in Winter Park

4.98 out of 5 average rating, 132 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.

4.97 out of 5 average rating, 197 reviews

An open living area showcases a black leather sectional couch arranged around a circular wooden coffee table adorned with greenery. Wooden accents highlight the walls, while soft lighting illuminates the adjacent kitchen and dining space visible in the background.

Townhouse in Winter Park

Modern/Rustic 2-bedroom Townhouse + Bonus Loft

Newly renovated modern/rustic three-story A-Frame townhome on the free shuttle route. Small and cozy, this 2 bedroom (+ lofted bed) can comfortably accommodate 5, but it should be noted that there's only 1 full bathroom! The location is perfect: it's quiet and serene while only being minutes from downtown Winter Park and two miles from the WP Resort. Vasquez Road is .4 miles from the front door to access everything the National Forest has to offer (hiking, snowshoe excursions, mountain biking)

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).

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, 160 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

4.84 out of 5 average rating, 647 reviews

The rustic cabin exterior is framed by tall aspen trees and features a wooden door. Bright flower boxes, filled with white and red blooms, add a pop of color in front of the porch area. A grill is positioned nearby on the deck.

Cabin in Winter Park

Cozy Cabin in Perfect Location

You've found the perfect cabin for your trip to Winter Park. Cozy, w/a queen bed & a single, pull-out couch. Small kitchen or -on a nice day- grill on back deck near creek. Electric fireplace adds ambiance. Tiny kitchen w/appliances, Keurig &dishes. STEPS away from Cooper Creek Town Square restaurants & Hideaway Park’s concerts. The City of Winter Park has trains going through the town, which adds to the charm. We love pets/dogs! 2 or more dogs require extra $10 per dog one-time cleaning fee.

4.95 out of 5 average rating, 164 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!

Experience Winter Park from an unbeatable location directly across from Winter Park Resort. Framed by stunning slope views, this beautifully appointed 3-bed/2.5-bath mountain retreat offers more than 1,800 square feet of spacious living for up to 8 guests. Spend your days skiing world-class terrain, hiking scenic trails, or exploring Winter Park’s dining, breweries, and live music, then return to the comfort of your own mountain escape. Winter Park Short-Term Rental Registration No. 005732

4.96 out of 5 average rating, 292 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

Guest suite in Winter Park

The exterior of a charming European-style home is displayed, featuring multiple windows with green shutters. A balcony adorned with vibrant flower boxes complements the rustic architecture. Lush greenery surrounds the property, enhancing its inviting appearance against a clear blue sky.

4.98 out of 5 average rating, 497 reviews

Charming Suite in Old Town Winter Park

Charming European suite steps away from a major ski resort. Located in the heart of Old Town Winter Park this beautiful European Country home is a welcoming retreat for mountain visitors. OUR LARGE PRIVATE SUITE IS IN THE LOWER LEVEL OF OUR HOME, complete with separate bedroom, kitchenette, hot tub, bathroom/shower & FREE PARKING! Take a 10-15 minute walk or short bus ride to the base of the Winter Park Resort to experience incredible skiing and boarding at any of the Resort's Territories.

4.96 out of 5 average rating, 101 reviews

Apartment in Fraser

3 BD/3 BA + BunkRoom + Top Floor Spa + MTN Views

Nestled in the heart of the picturesque Winter Park, Colorado, this exquisite 3-bedroom, 3-bath condo with full size beds bunk room is a perfect mountain retreat that combines rustic charm with modern comforts. Located on the top floor, this corner unit boasts high vaulted ceilings, offering an open and airy atmosphere that's further enhanced by stunning mountain views. Whether you're seeking a cozy winter haven or a refreshing summer escape, this condo promises an unforgettable experience.

4.99 out of 5 average rating, 154 reviews

Home in Winter Park

Pool Access & Mtn View! Luxe WP Cabin, Near Trails

Rendezvous Neighborhood | 1 Mi to Dtwn Bites & Brews | Walk to Fraser River Adventure begins right out your door at this Winter Park vacation rental, where alpine trails and fresh air set the stage for an unforgettable stay. Hike and bike through scenic terrain, or take advantage of Club MeadowRidge amenities just a short drive away. Then return to unwind in a beautiful cabin thoughtfully designed with custom furniture, modern amenities, and epic views. This is mountain living at its best!

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, 126 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.

4.95 out of 5 average rating, 173 reviews

Home in Fraser

Spacious Cabin • Family Friendly • Hot Tub • Views

Spacious mountain retreat in Winter Park with sweeping mountain and ski slope views. Minutes to Winter Park Resort, downtown, and Fraser, 30 mins to lakes and under 1hr to Rocky Mountain National Park. Relax in the private hot tub, gather around the fireplace, or enjoy open living with smart TVs, games, heated garage, grill, and outdoor dining. Easy access to hiking, biking and skiing. Comfortably sleeps 10, making it the perfect year-round Colorado getaway for families and groups.

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

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.

4.95 out of 5 average rating, 158 reviews

Tipsy Fox @ Downtown Winter Park Near the Slopes!

4.98 out of 5 average rating, 329 reviews

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.

Condo in Fraser

View • Fireplace • Hot Tub • Sauna • Pool

The cozy family room features a stone fireplace and a wall-mounted TV. Two brown leather armchairs are positioned near a round coffee table. Large windows provide natural light and impressive views of the Continental Divide, while artwork adorns the walls for added character.

5 out of 5 average rating, 26 reviews

Mountain Town Luxury Penthouse

4.94 out of 5 average rating, 33 reviews

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

4.97 out of 5 average rating, 122 reviews

A spacious living area is bathed in natural light from large windows, featuring a gas fireplace set against a stone backdrop. A comfortable couch provides seating, with a rustic coffee table styled with a chess set. Cozy decor elements, including soft blankets, enhance the inviting atmosphere.

Townhouse in Winter Park

Cozy Modern Cabin w/ Hot Tub - Minutes to Ski Area

A living area is showcased with a comfortable gray sofa and a warm electric fireplace. A large television is mounted on the stone wall. Natural light illuminates the space through windows, complemented by colorful wall accents and a cozy rug underneath.

4.88 out of 5 average rating, 344 reviews

Walk to Downtown | Hot Tub | Fire place | River |

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

The kitchen features light wood cabinetry and modern appliances, including a black stove and refrigerator. A large island with granite countertops provides seating with three wooden stools. A welcoming entry area is visible, complemented by a textured rug and a decorative door.

5 out of 5 average rating, 69 reviews

The Rustic Moose

Family- and pet-friendly home rentals

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.

4.83 out of 5 average rating, 101 reviews

Studio Downtown Winter Park

4.91 out of 5 average rating, 254 reviews

The modern kitchen features a large wooden dining table surrounded by white chairs, with panoramic windows offering expansive views of the mountains and forest. A sleek black appliance suite, including an oven and coffee maker, complements the space, while natural light fills the room.

Cabin in Tabernash

Mountain Getaway - Hot Tub & Sauna. Dogs welcome!

A modern living area features a comfortable leather sofa, accent chairs, and a coffee table. A fireplace is positioned beneath a flat-screen TV, with large windows allowing natural light to brighten the space. Artwork adorns the walls, adding a contemporary touch.

4.98 out of 5 average rating, 292 reviews

Beautifully Furnished Modern Condo In Downtown WP

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

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

4.93 out of 5 average rating, 698 reviews

Guest suite in Fraser

The Mountains are calling!

4.98 out of 5 average rating, 124 reviews

Cabin in Tabernash

Private Zen Retreat for Couples in Devil’s Thumb

4.99 out of 5 average rating, 128 reviews

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.

Condo in Fraser

Winter Park Getaway for Mountain Biking/Hiking!

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 127 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

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

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!

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.

5 out of 5 average rating, 101 reviews

Home in Winter Park

Luxury 3BR Winter Park | Hot Tub | Ski Shuttle

4.95 out of 5 average rating, 181 reviews

Cabin in Granby

Family Cabin on the Fraser | 3BR + River Front

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.

4.97 out of 5 average rating, 104 reviews

Mtn condo - hot tub, bus line, stocked kitchen

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.