Winter Park Lodging

Welcome to Alpenglow Retreat—your luxury escape in the heart of Winter Park! - Riverfront villa in downtown - Sleeps 8 with premium bedding - Rooftop deck w/ hot tub, minibar & views - Gourmet kitchen, fireplace, 73" Smart TV - Game room w/ NBA JAM arcade & Xbox - Walk to shops, dining & shuttle - 6 min drive to Winter Park Resort - Family-friendly: crib, booster seat, W/D - Heated two-car garage

Welcome to Cloud Nine Chalet, a luxurious, custom-built 6-bedroom mountain estate nestled in the heart of the prestigious Rendezvous neighborhood. With over 4,600 square feet of refined mountain-modern design, this brand-new retreat is more than a getaway—it's a destination for unforgettable summer moments, surrounded by nature’s beauty and elevated by thoughtful design.

Consider renting our charming two bedroom residence, which boasts excellent amenities, a generous floor plan and a wonderful neighborhood. It is conveniently located near the vibrant downtown area of Winter Park or offers easy access to the resort and various outdoor activities via a short shuttle ride. The residence’s ground floor features a spacious mudroom, providing ample storage and a designated area for outdoor equipment, along with convenient access to the private patio, with outdoor hot tub and is ideal for unwinding after outdoor activities.

Escape to Hygge Hideaway, a spacious 4-bedroom cabin in Winter Park’s Bear Trail neighborhood. Enjoy stunning mountain views, a private hot tub, and cozy nights by the fireplace. Perfect for families or groups, this rustic-chic retreat offers modern comforts like a chef’s kitchen, smart TVs, and luxury touches throughout. #HyggeHideaway #WinterPark #CozyCabin #MountainViews #HotTub #FamilyFriendly #GroupGetaway

Located in a quiet residential neighborhood of Fraser, 6 miles from the Winter Park Ski Resort, the Jabberwocky home is situated on almost an acre of land. This 3,200 square foot, 5 bedroom 4.5 bath home is spread over three floors, with plenty of room for everyone to relax. Amenities include a wood-burning fireplace in the living room, washer/dryer, private decks, and a pool table on the lower level of the home.

Mountain Wellness Retreat offers luxury and well-being in Winter Park’s vibrant downtown. Enjoy hypoallergenic linens, a $10k water filtration system, and spa-like amenities including a rooftop hot tub. With two king suites, a gourmet kitchen, and games for family fun, this serene retreat is designed for relaxation and adventure. Just minutes from dining, shopping, and the slopes. #MountainWellnessRetreat #WinterPark #LuxuryEscape #SpaExperience #SkiAndStay

Après Chalet is a luxurious 4-bedroom villa in the heart of Winter Park, blending modern style with mountain charm. Enjoy rooftop hot tub views, a game room, and high-tech features like Sonos and high-speed Wi-Fi. Just steps from Hideaway Park concerts, downtown dining, shops, and minutes from Winter Park Resort. Ideal for families or groups with sleeping for 12, a gourmet kitchen, and designer touches. Adventure awaits with hiking, biking, and skiing nearby.

Rocky Mountain Retreat is a luxurious 4-bedroom villa in the heart of Winter Park, offering stunning mountain views, a rooftop hot tub, and modern comforts. With 3,000 sq ft of stylish living space, this retreat is perfect for families or groups seeking both adventure and relaxation. Steps from downtown dining, shops, and slopes, it’s an ideal mountain escape. #RockyMountainRetreat #WinterPark #LuxuryVilla #MountainViews #HotTub #FamilyGetaway

A true log cabin getaway in this three-level home! Located in Fraser, this wonderful family rental offers a feeling of seclusion and great amenities. Easy access to downtown Fraser restaurants, breweries and summer hiking and biking trails. The free town shuttle stop is located approximately a mile away on the street. The main living area has vaulted ceilings with exposed wood beams to complement the open floor plan. Plenty of space to relax on sofas surrounding the wood stove; adjacent to the living space, the dining area seats up to 6. The oversized full kitchen has updated appliances and lots of cabinets and countertops space to make meal prep a breeze. The one bedroom has a Queen bed and full bathroom in the main hallway.

Welcome to Mountain Majesty – your private villa retreat high in the Winter Park peaks! -6BR, 5.5BA – sleeps 14 w/ media room & workspace -Hot tub, sauna, balcony w/ panoramic mountain views -Chef’s kitchen, stone fireplace and luxe finishes -Direct access to hiking trails & nature -Pet-friendly, high-speed WiFi, private garage