Family-Friendly rentals near Winter Park Resort

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)

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.

Cozy mountain retreat in downtown Winter Park

Lovingly remodeled Hi Country Haus 1 bedroom 1 bathroom condo central to downtown Winter Park. Use our Tiny Mountain Retreat as a launchpad to all the local access Winter Park has to offer or as a space for rejuvenation in this beautiful mountain town. Incredible access to local trail running, mountain biking, backpacking, fly-fishing, hiking and skiing. Grand Lake and Rocky Mountain National Park are easily and often visited from our spot as well. WP Short-term rental registration #019404

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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

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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.

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Ski-In Ski-Out Zephyr Mtn Lodge Condo w/ Hot Tub

Enjoy your stay right next to the Gondola here at the Zephyr Mountain Lodge - Winter Park Resort's premier ski-in/ski-out base lodging. This 1-bedroom, 1-bathroom condo is ideal for a small family or couple seeking mountainside convenience and complimentary amenities. Enjoy a direct ski-in/ski-out location, where winter adventures and summer endeavors are easily in reach! End each day with ease - whether you're soaking in the community hot tub or warming up by the unit’s fireplace.

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!

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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, retreat to a fully private primary suite with ensuite bath. The second bedroom, just off the entryway, has its 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.

Luxury Ski-In Ski-Out Ski to Winter Park Resort

Elevate your getaway in this cozy mountain condo, wrapped in mid-century charm and breathtaking views. Enjoy the mini Pub, snuggle up by the fireplace, or take in the mountain views. Sleep in luxurious comfort, and dine with a ski lift mural as your photo-worthy backdrop. Put a vintage record on, host a game night marathon, or soak in the infinity-style hot tub. The slope is located directly behind the building and you can walk or ski to the Winter Park Resort village center.

One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit

Located in the Winter Park Village, walking distance to The Gondola this condo has it all! The bedroom features a King bed with a memory foam pull out Queen in the living area. Complete Kitchen, full size fridge, dishwasher, large bathroom, and private covered patio with views of the Mountain. Walking distance to shopping, restaurants, & activities! One of only a handful of units with direct outdoor access. UPDATE: New hot tub is OPEN! Permit #009238

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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.

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Top floor, larger 1 bedroom in Winter Park Village

Conveniently located in the Winter Park Village at Fraser Crossing, this updated and oversized 1 bedroom condo sleeps 4 comfortably with a FULL KITCHEN!!! Enjoy the views that come with this peaceful and conveniently located penthouse unit. Close to entertainment, activities, restaurants, ice skating rink, and adventure! Most importantly, a short 2 minute walk to the Gondola...park your car and forget about it.