Holiday rentals with outdoor seating in Winter Park

Mountain Modern Cozyville

Remodeled with a high end modern flair for comfort and a classic mountain style A mountain-modern, warm, and cozy space that's conveniently located in a quiet mountain-view neighborhood with FREE recreation-center benefits right across the street and a FREE local bus system right out the front door to all local attractions. Safeway, coffee shops, ski/ride/hike stores less than 1-mile away. It really doesn't get any better than this! We will look forward to your feedback and adventure stories.

30 mi to Rocky Mt- 270* Views - Private Hottub

Welcome to the Alpenglow Mountain Gateway! In this funky mid mod 2 bedroom/ 2 bathroom townhome you will find all the creature comforts within the confines of our beautiful wood paneled solar townhome. Private hottub!! Every room is complimented by the expansive mountain views. Eastward is Byers Peak & West the Continental Divide, making sunsets/ sunrises an unmissable time. Winter Park resort 9 mins away Bus stop right outside door Less than a mile to supermarket, restaurants and breweries

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 (+ loft) space 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)

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!

Beautiful Spacious 2 Bedroom & Loft Mountain Condo

Located right in the middle of all things Rocky Mountains. You're just 30 minutes from Grand Lake/Rocky Mountain National Park/Winter Park and 2 mins from skiing, fishing, golf, and mountain biking at Granby Ranch. This corner unit has lots of space at 1200 square feet. Between the king size bed in the master, a queen bed in the 2nd bedroom, and a queen size sleeper sofa in the upstairs loft, the condo is able to sleep 6. We only allow 4 guests, but could accommodate on a case-by-case basis.

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.

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

Welcome to Leone’s Den. This newly renovated studio condo located at the base of Winter Park Resort. Walk less than 150 yards to the slopes! Shops, restaurants, and bars at the Village Base just across the street and a pool sized hot tub! Marvel at the beautiful mountain views from the largest hot tub in Winter Park, brand new in 2025. Enjoy the view of village and mountain landscape while enjoying the warmth of the fireplace. The studio has everything you need for an unforgettable stay.

Walk to Restaurants! Bring your Fishing Pole!

There's still time to hike and bike before the snow falls! Don’t miss this spacious 1 BR Fraser condo perfectly located for your fall adventures; National Park visits, hiking, biking, and other recreation in Grand County! The pond is stocked with fish! You are just a short walk from Safeway, restaurants, breweries and the Fraser River and Trail. You are a .8 mile walk from the train station which offers daily Amtrak service and are steps away from the free Lift shuttle service.

Main Street Luxury: Downtown with Hot Tub & Trails

You'll feel right at home at the hearth of this updated condo. You'll be on the slopes in 2 bus stops with pickup just outside. On Main Street, across from Cooper Creek and the Rendezvous Event Center, the town awaits. Host family style feasts with the fully equipped kitchen and dine up to nine. Relax in the hot tubs, on the huge couch by the big screen digital cable TV with streaming services, on the deck and in the hot tubs. Decadent Cal King bed in master. Ski lockers.