Family-friendly holiday rentals in Winter Park

4.93 out of 5 average rating, 206 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

Private luxury mountain home on 3 acres! Amazing Mountain View’s and only 2 miles off hwy 40 and 9 minutes to Granby Ranch- 20 minutes to Winter Park- Amazing ski or mountain getaway for up to 4 families. Large deck with large hot tub. 2 master suites with king beds and en-suite bathrooms. 3rd bedroom sleeps a family of three with a queen bed and single twin bunk. 4th bedroom/Huge family/ teen room with 5 queen beds built into the wall with bathroom. A true CO Retreat in a great location.

FamilyKitchenValue

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, 201 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)

FamilyIndoor spacesDecor

4.91 out of 5 average rating, 255 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!

Escape to our luxury Colorado mountain retreat with stunning Continental Divide views! Comfortably sleeps 8. Features a chef's kitchen, indoor 6-person hot tub & sauna, and wood-burning fireplace. Family-friendly with a bunk room and travel crib. Just 15 mins to Winter Park Ski Resort & 30 mins to Rocky Mountain National Park in summer months. Perfect for adventure and relaxation. We love dogs and they’re welcome in our home! Please make sure to add them to the booking so we know they’re coming.

Indoor spacesFamilyOutdoor spaces

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.

FamilyIndoor spacesBathroom

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, 179 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).

FamilyIndoor spacesCheck-in

4.98 out of 5 average rating, 331 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

KitchenIndoor spacesWalkability

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

Indoor spacesFamilySkiing

4.96 out of 5 average rating, 293 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

Indoor spacesFamilyHospitality

4.95 out of 5 average rating, 176 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

Experience nature in this scenic 4-bedroom, 3-bathroom chalet that is secluded amongst the trees and river yet close to everything. Choose having your morning beverage nestled in front of the fireplace or in a hot tub overlooking the river. The property is perfectly situated with downtown 1 mile away, Winter Park Resort within a 10 minute drive and 75 steps from the Lift bus route too. Or, stay around the house with access to beautiful hiking and mountain biking trails just 1 block away!

Indoor spacesFamilyView

4.96 out of 5 average rating, 105 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.

FamilyIndoor spacesAmenities

4.95 out of 5 average rating, 174 reviews

Home in Fraser

Spacious Cabin with Views • Location • Hot Tub

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.

FamilyIndoor spacesHot tub

4.84 out of 5 average rating, 113 reviews

A warm wooden cabin is set against a backdrop of tall evergreen trees, blanketed in snow. The scene captures a serene winter day, with fluffy clouds drifting in a bright blue sky. Snow-covered paths lead towards the entrance of the inviting retreat.

Cabin in Winter Park

Moose House in Perfect Location!

PERFECT LOCATION with a CREEK in the backyard! > Sleeps 13 guests comfortably > 4 bedroom > 3 Baths > 2 Fireplaces > HotTub for 8 > Town square directly across street - restaurants, shops, 2 min. walk. **This property is also perfect for family reunions and small private weddings. For larger groups than 13, there is also a smaller cottage on the same property for rent, which can sleep 3 more guests. Both properties can be rented together. Please contact us to coordinate.

FamilyIndoor spacesCheck-in

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

4.99 out of 5 average rating, 155 reviews

Home in Winter Park

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

Indoor spacesFamilyLaundry

4.96 out of 5 average rating, 114 reviews

Downtown Mtn Oasis + Hot Tubs | Steps to Events

FamilyKitchenAccuracy

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, 121 reviews

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

Indoor spacesFamilyLayout

4.97 out of 5 average rating, 32 reviews

Luxury Winter Park Retreat with Private Hot Tub

Indoor spacesFamilyCleanliness

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.

5.0 out of 5 average rating, 26 reviews

Mountain Town Luxury Penthouse

KitchenIndoor spacesBarbecue

5.0 out of 5 average rating, 18 reviews

Mountain Condo w/ Hot Tub | Walk to Town | Ski Bus

Indoor spacesFamilySleep quality

4.92 out of 5 average rating, 12 reviews

A spacious dining area features a large wooden table surrounded by black and white chairs, positioned near expansive windows. The open concept connects to a modern kitchen, with light streaming in and providing views of autumn foliage outside.

Home in Fraser

Winter Park home new listing

KitchenIndoor spacesBarbecue

A modern building is visible on the left, surrounded by snow-covered ground and tall evergreen trees. A clear blue sky is overhead, with the sun shining brightly in the upper right corner. A snow-packed path leads through the winter landscape, inviting exploration.

5.0 out of 5 average rating, 48 reviews

Modern New build ski in/out. 1br + den.

KitchenFamilyCondition

Family- and pet-friendly home rentals

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

Indoor spacesKitchenQuiet

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, 294 reviews

Beautifully Furnished Modern Condo In Downtown WP

FamilyIndoor spacesSolo travel

4.97 out of 5 average rating, 501 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!

Indoor spacesFamilyGetting around

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, 160 reviews

Tipsy Fox @ Downtown Winter Park Near the Slopes!

Indoor spacesFamilyParks

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, 131 reviews

Luxury Winter Park Studio*PrivHotTub*Majestic View

KitchenIndoor spacesLaundry

An expansive wooden deck is shown, featuring rustic log railings. Breathtaking views of lush green mountains and a clear blue sky are visible in the background, inviting appreciation of the natural surroundings.

4.94 out of 5 average rating, 156 reviews

Winter Park Mountain Views with Relaxing Hot Tub

KitchenFamilyWalkability

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

FamilyIndoor spacesComfort

4.97 out of 5 average rating, 101 reviews

Chalet in Granby

Lone Eagle Chalet at Granby Ranch - With Hot Tub!

KitchenFamilyWalkability

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 134 reviews

Sleeper@SnowBlaze! Great Location! Hot Tubs/Pool!

KitchenIndoor spacesLong stay

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, 259 reviews

Homebase Snowblaze

FamilyIndoor spacesCondition

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, 164 reviews

Cozy mountain retreat in downtown Winter Park

KitchenFamilyAccuracy

A cozy living space is featured, showcasing a dark leather sofa with a lavender throw pillow. A wall-mounted television is positioned above a white-brick fireplace. Light hardwood flooring extends throughout, while large windows allow natural light to brighten the room.

4.94 out of 5 average rating, 104 reviews

Beautiful Condo at Winter Park!

FamilyIndoor spacesHospitality

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, 153 reviews

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

Indoor spacesKitchenTV

5.0 out of 5 average rating, 102 reviews

Home in Winter Park

Luxury 3BR Winter Park | Hot Tub | Ski Shuttle

KitchenFamilyLayout

4.87 out of 5 average rating, 253 reviews

A cozy living area is highlighted by a stone fireplace and wooden accents. A sectional sofa faces a coffee table adorned with decorative items. A dining table for four is visible, set against the backdrop of a well-equipped kitchen with modern appliances.

Condo in Granby

Sandy and Ryan's Granby Getaway!

Indoor spacesKitchenGetting around

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.