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Family-friendly holiday rentals in Winter Park

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Quick stats about holiday rentals that are family-friendly in Winter Park

  • Total holiday rentals

    Explore 1,260 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $129 AUD per night before taxes and fees

  • Verified guest reviews

    Over 31,010 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 220 rentals that welcome pets

  • Holiday rentals with a pool

    310 properties feature pools

  • Rentals with dedicated workspaces

    790 properties have a dedicated workspace

  • Wi-Fi availability

    1,260 of Winter Park holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Park rentals

  • 4.8 Average rating

    Winter Park stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Winter Park

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
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
4.98 out of 5 average rating, 131 reviews

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.

Indoor spacesKitchenLaundry

Guest favourite
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
4.97 out of 5 average rating, 192 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 spacesAccuracy

Guest favourite
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
4.84 out of 5 average rating, 641 reviews

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.

FamilyIndoor spacesLayout

Guest favourite
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.
Condo in Winter Park
4.93 out of 5 average rating, 280 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.

Indoor spacesFamilyWalkability

Guest favourite
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.
Condo in Winter Park
4.88 out of 5 average rating, 254 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.

FamilyIndoor spacesWalkability

Guest favourite
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
4.97 out of 5 average rating, 120 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.

Indoor spacesFamilyNearby

Top Guest favourite
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
4.96 out of 5 average rating, 289 reviews

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

KitchenIndoor spacesParking

Top Guest favourite
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.
Guest suite in Winter Park
4.98 out of 5 average rating, 495 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.

KitchenIndoor spacesHot tub

Guest favourite
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.
Condo in Winter Park
4.85 out of 5 average rating, 114 reviews

Prime location, amazing views, stylish, sleeps 7

Relax and unwind at this stylish, centrally-located condo. Features include an updated kitchen as well as both bathrooms, a cozy fire place, spacious patio to enjoy morning coffee with incredible views all season. Located just 0.5 miles from downtown Winter Park you can easily walk to restaurants and shops. A shuttle stop to Winter Park Resort is conveniently located just outside the front door making the slopes just minutes away. Easy access to biking/hiking trails as well as Wolf Park.

Indoor spacesKitchenAccess

Top Guest favourite
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
4.97 out of 5 average rating, 494 reviews

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.

KitchenIndoor spacesCheck-in

Top Guest favourite
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.
Apartment in Winter Park
4.97 out of 5 average rating, 120 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.

KitchenIndoor spacesCondition

Top Guest favourite
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
4.95 out of 5 average rating, 164 reviews

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

FamilyKitchenQuiet

Popular amenities for Winter Park family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Superhost
Three mid-century-inspired A-frame cabins are nestled among tall evergreen trees, surrounded by a snowy landscape. The cabins feature triangular roofs and natural wooden exteriors, creating a harmonious blend with the mountain scenery. Snow-covered ground and trees enhance the serene atmosphere of the setting.
Cabin in Winter Park
4.78 out of 5 average rating, 194 reviews

Mountain Cabin

KitchenIndoor spacesCheck-in

Guest favourite
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.
Condo in Winter Park
4.92 out of 5 average rating, 169 reviews

Hideaway Park! Hot tub,Pool,FitnessCtr&FreePrkg

FamilyKitchenWi-Fi

Top Guest favourite
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
4.98 out of 5 average rating, 326 reviews

View • Fireplace • Hot Tub • Sauna • Pool

KitchenIndoor spacesLaundry

Top Guest favourite
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.
Apartment in Winter Park
4.98 out of 5 average rating, 288 reviews

Beautifully Furnished Modern Condo In Downtown WP

KitchenIndoor spacesLaundry

Guest favourite
Condo in Winter Park
4.93 out of 5 average rating, 30 reviews

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

FamilyIndoor spacesHiking

Guest favourite
An open concept living area is highlighted by a modern gas fireplace set against a stone wall. A spacious sectional sofa faces the fireplace, complemented by a decorative area rug. Large windows fill the space with natural light, showcasing stylish furnishings and a dining table for six.
Home in Winter Park
4.96 out of 5 average rating, 72 reviews

Downtown WP Cabin 44 - Hot Tub - Views - Bunks

KitchenFamilyBathroom

Guest favourite
The log cabin is framed by blooming yellow flowers and lush greenery, with a soft sunset sky in the background. Warm light spills from the windows, creating an inviting ambiance that highlights the cabin's rustic charm and natural surroundings.
Cabin in Winter Park
4.81 out of 5 average rating, 316 reviews

Charming Log Cabin w/hot tub in Winter Park CO!

Indoor spacesFamilyLocation

Guest favourite
Apartment in Winter Park
5 out of 5 average rating, 9 reviews

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

FamilyIndoor spacesPets

Family- and pet-friendly home rentals

Top Guest favourite
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
4.98 out of 5 average rating, 126 reviews

Luxury Winter Park Cabin w/Hot Tub & Pet Friendly

Indoor spacesFamilyLong stay

Guest favourite
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.
Apartment in Winter Park
4.83 out of 5 average rating, 100 reviews

Studio Downtown Winter Park

KitchenFamilyLong stay

Top Guest favourite
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.
Apartment in Winter Park
4.95 out of 5 average rating, 153 reviews

Tipsy Fox @ Downtown Winter Park Near the Slopes!

KitchenFamilyLong stay

Guest favourite
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
4.91 out of 5 average rating, 252 reviews

Mountain Getaway - Hot Tub & Sauna. Dogs welcome!

FamilyKitchenCheckout

Guest favourite
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.
Apartment in Winter Park
4.96 out of 5 average rating, 139 reviews

Calm vibes and a great view at the Alpen Rose

FamilyKitchenParks

Guest favourite
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.
Condo in Winter Park
4.75 out of 5 average rating, 198 reviews

Great Condo right on the Creek License #005702

KitchenIndoor spacesAmenities

Guest favourite
A well-lit common room features large windows with views of surrounding trees. Cozy seating arrangements include a comfortable sofa and two armchairs. A dining area with wooden chairs and a table is present. A television is located on a shelf beside a small bookshelf.
Apartment in Winter Park
4.8 out of 5 average rating, 137 reviews

The Alpen Rose- Cozy cabin feel w/amazing Views

Indoor spacesKitchenHeating

Top Guest favourite
Guest suite in Fraser
4.93 out of 5 average rating, 694 reviews

The Mountains are calling!

Indoor spacesKitchenLayout

Family-friendly home rentals with a pool

Superhost
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.
Condo in Winter Park
4.72 out of 5 average rating, 293 reviews

Entire Condo In The Heart of Winter Park

FamilyIndoor spacesAir conditioning

Top Guest favourite
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
4.97 out of 5 average rating, 123 reviews

Cozy Cabin on the Fraser River

Indoor spacesKitchenQuiet

Guest favourite
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.
Condo in Winter Park
4.88 out of 5 average rating, 112 reviews

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

FamilyKitchenBiking

Guest favourite
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.
Condo in Fraser
4.9 out of 5 average rating, 151 reviews

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

Indoor spacesKitchenNearby

Top Guest favourite
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.
Condo in Winter Park
4.91 out of 5 average rating, 322 reviews

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

KitchenIndoor spacesValue

Guest favourite
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.
Condo in Winter Park
4.94 out of 5 average rating, 118 reviews

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

FamilyKitchenNearby

Guest favourite
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.
Condo in Winter Park
4.94 out of 5 average rating, 158 reviews

Cozy mountain retreat in downtown Winter Park

FamilyIndoor spacesBathroom

Guest favourite
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.
Condo in Winter Park
4.77 out of 5 average rating, 150 reviews

Perfect ski Condo

FamilyKitchenLocation

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$449 AUD$446 AUD$423 AUD$324 AUD$260 AUD$285 AUD$298 AUD$275 AUD$268 AUD$291 AUD$315 AUD$488 AUD
Avg. temp-7°C-7°C-3°C-1°C4°C9°C13°C12°C8°C2°C-3°C-7°C

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