Holiday rentals in Winter Park

Hideaway Park! Hot tub,Pool,FitnessCtr&FreePrkg

BEST Location in Winter Park!!Trailhead condos offer a year-round heated pool, hot tub, fire pit, patio, clubhouse, large indoor lounge, fitness room & game room. Just steps to Fraser River trail, restaurants, shopping and free ski shuttle. *On Hideaway Park* Access to Summer concerts&festivals, playground, picnic area, fire pit, and skate park to entertain kids! Relax by the fire or private furnished covered deck. Top floor (w/elevator) corner unit w/views! Pets welcome! (w/add'l clean fee).

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!

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.

Luxury Mtn Cabin/Free Shuttle/ Views/Garage

Escape to Mountain Flower Cabin located in the Rendezvous community just a short walk to downtown Winter Park and a 4 mile shuttle ride (free) to Winter Park Ski Resort. Our 3BR cabin is well appointed with custom furniture, modern amenities, and breathtaking mtn views. Nestled within the Rendezvous Trail System, alongside the Fraser River, you'll find miles of hiking, biking, fishing and cross country skiing right outside your door. The free shuttle to WP is steps from the cabin.

Main St Luxury, Hot Tub & Steps to Brew & Trails

You'll feel right at home at the hearth of this updated condo. You'll be on the slopes in two 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.

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

Winter Park Studio: On the River~ Walk Downtown!

Fireside Haven is a cozy studio located on a secluded spot RIGHT on the Fraser River, yet is walkable to all that downtown Winter Park has to offer. Dine-out, shop, enjoy coffee at a café, cocktails at happy hour, hike/bike and catch the ski shuttle all within a five-minute walk from your front door! You will have a king-size bed, queen-size sofa sleeper, full kitchen, bathroom, fireplace, private patio & ski closet.

Updated Condo | Washer Dryer | Steps to Shuttle

This 1 bed 1 bath condo provides all the essentials for your stay and the light and open floor plan makes you feel right at home. Located walking distance from trails, shuttle stop, supermarket, coffee shops, local restaurants, and just an 8-minute drive to the base of Winter Park. A small pond with benches and mountain views sits behind the unit, offering additional outdoor space right at your fingertips.