Family-friendly holiday rentals 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)

Family · Kitchen · Getting around

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!

Kitchen · Family · Condition

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

Family · Indoor spaces · Hot tub

NEW+ Winter Park+ Hot Tub+ Garage+ Coffee bar

New Modern condo with private hot tub, garage, and stunning alpine views near Winter Park Ski Resort. 🚗 Attached garage with direct access 🔑 keyless entry- personlized code for safety 💦 Private 7-person hot tub ♿️ Wheelchair accessible single-level 1st floor ☕️ Coffee & espresso bar (pods included) 🚴 Bike hose & secure storage 💻 Remote work ready: ½ GB WiFi, desk & monitor 🛏 New premium mattresses 🍳 Fully stocked kitchen 📺 55” Smart TV in living room + TVs in bedrooms 🧺 washer/dryer

Family · Kitchen · Bathroom

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.

Family · Indoor spaces · Location

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 spaces · Kitchen · Getting around

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.

Indoor spaces · Family · Nearby

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!

Indoor spaces · Kitchen · Laundry

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.

Kitchen · Indoor spaces · Hiking

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.

Family · Kitchen · Sleep quality

Beautiful Condo at Winter Park!

Beautiful one bedroom condo that sleeps up to 6 and situated at one of the best locations at Iron Horse. All amenities including pool, hot tub, fitness center, and garage are in the same building! Walk across the sky bridge and you’re at the corridor run connecting the base of Mary Jane to the base of Winter Park. Condo includes a king, queen Murphy, and one queen plus bed from a new American leather sleeper sofa. Completely equipped kitchen and great place for all activities!

Indoor spaces · Family · Getting around

Ski In/Ski Out - Modern Cozy Condo in Winter Park

Leone’s Den | A Boutique Mountain Retreat at the Base of Winter Park Resort Step into refined alpine comfort at Leone’s Den, an elegant studio just steps from the slopes. Located across from the Village Base, enjoy easy access to dining, shopping, and après-ski, then retreat to a warm space with a cozy fireplace and elevated finishes. Relax in Winter Park’s largest hot tub and return to plush linens and beautiful mountain and village views.

Kitchen · Indoor spaces · Sleep quality