Kid-friendly holiday rentals in Winter Park

4.82 out of 5 average rating, 131 reviews

Loft in Granby

Ski in/out- Sleeps 8 Granby Ranch Mountainside #69

Ski in/out at Granby Ranch. Sleeps 8. Skiing, snowmobiling, sleighrides, & more in beautiful Granby, CO. Luxurious condo w/ loft slope side of family friendly Mountainside Granby Ranch Ski Resort. Features 3 bedrooms (king in master), 3 bathrooms, FULL SIZE WASHER/DRYER, stocked kitchen w/ large dining room table, comfortable reclining living room furniture, and more. Upscale updates throughout. Loft enclosed for privacy, bathrooms fully remodeled. Graco Pack n play in unit! Free and Fast WIFI!.

4.89 out of 5 average rating, 227 reviews

Condo in Winter Park

Ground floor 2 bedroom, at Hi Country Winter Park

Recently remodeled 2-bedroom GROUND floor condo is located on the Fraser River, one block away from the main strip of WP. The Hi Country complex features a newly remodeled clubhouse with indoor & outdoor hot tubs, large pool, fitness center, pool table, kids room, and an outdoor playground. In the winter, the free shuttle is located 45 steps behind our building and will whisk you to the ski area twice an hour. A 5-15 min walk to shops, restaurants, bars, movie theater, and the town park.

Top Guest favourite

Cabin in Winter Park

4.94 out of 5 average rating, 199 reviews

Cozy Log Home,Sleeps 10. Free shuttle,3 min-slopes

Location doesn’t get better! Highly desirable area in WP. Free shuttle steps from door. Newly remodeled! Outstanding Views of slopes/Continental Divide. 3-4 min drive to slopes & 1 1/2 min-Main to Main St. shops,dining, bars, concert amphitheater/fairs etc. High-end grill, Lg Deck! New smart tv in living room w/ Sonos soundbar to play music from phone. WIFI 1 GB, cable, games. Every kitchen amenity! Our own Quality bedding/linens. Cleaned/Sanitized at each checkout! Short term license #005200

4.9 out of 5 average rating, 132 reviews

Ideal Winter Park Retreat – Ski, and Relax!

This fantastic end-unit townhouse offers the perfect blend of convenience and serenity. Located on the shuttle line and just minutes from town, it’s nestled among towering pines for a peaceful, secluded feel, yet close to all the action. Featuring stunning mountain views, this light and bright home includes: private hot tub with views, fully-stocked kitchen, and split level bedrooms for privacy. The perfect base for all your Winter Park adventures—whether skiing or just unwinding in nature!

4.83 out of 5 average rating, 157 reviews

Family friendly great to hike bike & walk to town

Modern but classic and cozy Winter Park escape. Ample privacy, space and nature. 5 minutes walk to town of Winter Park and national forest with many nature trails to hike, mountain bike and snow shoes. Shuttle to Winter Park resort picks you up at the bottom of the driveway. Perfect for friends, couples, and families. Several porch and deck areas with great views of an Aspen Grove. Lots of hummingbirds and the sound of a river nearby. Clean and comfortable bed areas and a great fireplace.

4.96 out of 5 average rating, 28 reviews

Apartment in Fraser

3BR/3BA + Bunk room w/ Hot tub

Stunning Mountain views enjoyed from your private hot tub await at this brand-new 3BR/3BA + Bunk Room condo located minutes from downtown Winter Park. Oversized windows provide ample natural light for this open-concept floor plan which includes a fully stocked kitchen, so preparing meals for large groups is a breeze. Features include vaulted ceilings, a ski locker, walking distance to the ski shuttle, radiant floor heating, gas fireplace, 5 smart TVs, in-unit W/D, puzzles, and many games.

4.78 out of 5 average rating, 158 reviews

Home in Granby

Granby Getaway

Get ready for a relaxing retreat in a beautiful new home with absolutely STUNNING views of Lake Granby and the mountains. Big windows provide beautiful views from every room. Our large wrap around deck allows you to enjoy the fresh Rocky Mountain air without ever leaving the home, while the central location gives you access to everything you are looking for in a mountain vacation. We have child amenities available to make packing easier, and pups are welcome to join you for a pet fee.

4.93 out of 5 average rating, 287 reviews

Cabin in Idaho Springs

Mountain Vacation Home with Amazing views

This cozy cabin is close to family-friendly activities. You’ll love your stay because of the the views, high ceilings, privacy and the location. The cabin is great for couples, solo adventurers, and families (with kids) There are TVs with cable in the bedrooms and living room, a hot tub to soak in and enjoy how close the stars shine. PLEASE NOTE: This Vacation home's elevation is 10800 feet. The weather is unpredictable- From September to May 4 wheel drive is required!

4.96 out of 5 average rating, 136 reviews

Apartment in Winter Park

Amazing Condo at the Base of Winter Park Resort

Our home at the base of the Winter Park Resort (100 meters from the Gondola) is updated (paint, furniture, lighting, bedding, kitchen supplies), clean, and modern to provide a cozy and comfortable base for every mountain activity: Ski, bike, play, hike, relax, and renew with a hot tub only 2 meters away. King bed, comfortable queen sleeper and a port-a-crib if you need it make this great for a family/group retreat. Winter Park Short-Term Rental Registration No. 4328

4.91 out of 5 average rating, 201 reviews

Beautiful Townhome in Downtown Winter Park!

(Winter Park short term rental no. 004831) Townhouse in the heart of downtown Winter Park is perfect for families and large groups! This home is steps away from Hideaway Park and the ski bus. With beds for 10 people, private bathrooms & a garage/driveways that can fit 4 cars, this home is ideal for groups. The kitchen is fully stocked with everything you need. For young children, we have everything from a high chair to a stroller to toys to a pack and play.

4.83 out of 5 average rating, 36 reviews

The Camping Bear

Welcome to "The Camping Bear" - Your Ultimate Mountain Retreat! Nestled in the heart of Winter Park, our cozy home is the perfect base camp for all your mountain adventures. With the Winter Park Lift right across the street, Winter Park Resort and trailheads mere minutes away, and downtown Winter Park within walking distance, you're in for an unforgettable experience. After adventure-filled days, unwind in comfort in our fully-equipped home.