Family-friendly vacation 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, 127 reviews

A mountain home featuring a large deck and expansive windows that showcase the surrounding nature. The stone chimney adds a rustic touch to the exterior, while the driveway is bordered by a wooden fence. The structure is complemented by a well-maintained landscape.

Home in Fraser

5 Acres, Hot Tub w/Mountain Views, Sledding Hill!

Beautiful mountain home with panoramic mountain views, located on 5 private acres. Home sleeps 14 and features 5 bedrooms and 3 newly renovated baths, along with a recently remodeled kitchen with granite counters and a magnificent wood-burning fireplace. Relax in the hot tub under the stars after a day of skiing or hiking. Park and store your gear in the 4-car garage. Our retreat is only two miles from downtown Fraser and 12 minutes to Winter Park ski area. *Please note: We do not allow events.

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.

4.97 out of 5 average rating, 195 reviews

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.

4.92 out of 5 average rating, 171 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 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, 156 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!

4.98 out of 5 average rating, 327 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

Welcome to our favorite place in the mountains We've been sharing our family getaway with guests for years; there's nothing we love more than hearing that someone watched the sunrise with a cup of coffee on the deck, came back from skiing to relax by the fireplace, or spent the evening laughing around the table together We hope you'll feel right at home here And yes...we're dog people🐾 We know vacations are better when the whole family comes along, so well-behaved dogs are warmly welcomed

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.

4.95 out of 5 average rating, 164 reviews

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

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, 282 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 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.

4.97 out of 5 average rating, 121 reviews

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

Welcome to your modern cabin in the woods, the Bear Cabin. Ideally situated in Rendesvouz, with quick access to downtown Winter Park, Winter Park ski area (free shuttle), and miles of trails. Well-appointed with high-end finishes and a hot tub! Luxurious finishes include a stone fireplace (gas), wide-plank hardwood floors, marble countertops, designer tile, and a hand-hewn beam and mantle. Well-appointed kitchen w/ everything needed for cooking. 2 private bedrooms + loft space with bunk beds.

4.96 out of 5 average rating, 291 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

4.96 out of 5 average rating, 99 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.

A spacious living area features a sleek Lovesac Sactional couch arranged around a modern coffee table. A stone fireplace enhances the warmth of the space, while large windows provide expansive views of the valley and access to a private deck. Wood beams and a spiral staircase add architectural interest.

5 out of 5 average rating, 129 reviews

Best Views In WinterPark | FamilyFriendly | Garage

COME FOR THE FUN AND STAY FOR THE BEST VIEWS IN WINTER PARK :) Your 3BR/3BA 1,300+ sqft Family Friendly Condo with Private Garage lives like a Townhome with ample space & privacy for everyone in your group. Upstairs you'll find a fully private master bed with ensuite bath. The 2nd bedroom is super private located right off the entryway with it's own private ensuite full bath as well. At the Winter Park Retreat you'll enjoy spectacular views from your private deck and throughout the home.

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

The living space features a modern kitchen with stainless steel appliances and a sleek bar area. A leather sofa and armchair surround a round coffee table, creating a comfortable seating arrangement. A colorful artwork hangs on the wall, complemented by stylish lighting fixtures.

4.99 out of 5 average rating, 118 reviews

Winter Park Condo on the River: Walk to Downtown!

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, 25 reviews

Mountain Town Luxury Penthouse

4.94 out of 5 average rating, 32 reviews

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

5 out of 5 average rating, 25 reviews

Luxury Winter Park Retreat with Private Hot Tub

A spacious living area features a large sectional sofa adorned with blue and yellow cushions. Tall windows provide views of the mountains, while a ceiling fan hangs above. A soft area rug complements the room's neutral color palette, adding warmth to the inviting space.

4.99 out of 5 average rating, 80 reviews

Luxury Condo on Main Street - Winter Park, CO

5 out of 5 average rating, 11 reviews

Home in Fraser

Luxury Mountain Home • Views + Hot Tub

4.95 out of 5 average rating, 74 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

4.95 out of 5 average rating, 175 reviews

A secluded chalet is surrounded by towering trees and located next to a gently flowing river. The dark wood structure features large windows and a spacious deck, inviting a connection with nature and providing serene views of the natural landscape.

Home in Winter Park

Winter Park Creekside Chalet with Hot Tub

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 126 reviews

A spacious, modern home is nestled among tall trees, with a welcoming exterior featuring a combination of rustic and contemporary designs. The garage doors and entryway are clearly visible, with a scenic backdrop of mountains and a blue sky dotted with fluffy clouds.

Townhouse in Fraser

Luxury Winter Park Cabin w/Hot Tub & Pet Friendly

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 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, 123 reviews

Luxury Winter Park Studio*PrivHotTub*Majestic View

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, 291 reviews

Beautifully Furnished Modern Condo In Downtown WP

4.93 out of 5 average rating, 697 reviews

Guest suite in Fraser

The Mountains are calling!

5 out of 5 average rating, 32 reviews

Home in Winter Park

The Perch | Cozy + Modern Cabin w/ Hot Tub

4.92 out of 5 average rating, 182 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, 122 reviews

Cabin in Tabernash

Private Zen Retreat for Couples in Devil’s Thumb

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 124 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

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, 152 reviews

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

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, 116 reviews

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

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, 159 reviews

Cozy mountain retreat in downtown Winter Park

Superhost

A modern living area features a deep blue sofa adorned with decorative pillows, a glass coffee table, and a cozy textured rug. Natural light filters in through large windows, highlighting a dining area and a spiral staircase that leads to the loft space above.

Condo in Fraser

4.89 out of 5 average rating, 164 reviews

Newly Renovated Mountain Modern Condo

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!

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

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.