Winter Park Lodging

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.

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.

Escape to Alpine Vista Lodge, a luxury mountain retreat in Bear Trail, just 5 mins to Winter Park Resort. Enjoy breathtaking ski slope views, a private hot tub, chef’s kitchen, and upscale amenities for all ages. Cozy up by the fire, soak under the stars, or explore downtown Winter Park just 2 mins away. Your elegant year-round basecamp for adventure, comfort, and connection.

Luxury Alpine Abode is a stunning 2,000 sq. ft. loft in Winter Park’s new ROAM neighborhood, featuring panoramic mountain views, a rooftop hot tub, and cozy fire pit. Perfect for up to 10 guests, with two master suites, a chef's kitchen, and spacious living areas. Steps from downtown and a quick shuttle to Winter Park Resort, it's the ideal retreat for families or friends seeking luxury and adventure. #LuxuryAlpineAbode #WinterPark #MountainViews #HotTub #GroupGetaway #SkiAndStay

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

Discover luxury at Trademark Views, a stunning 4-bedroom retreat just half a mile from the slopes. Enjoy mountain views, a private hot tub, a crackling fireplace, and a spa-like primary suite. With high-speed WiFi, a free resort shuttle, and endless adventure steps away, this is your perfect Winter Park escape. #TrademarkViews #WinterParkLuxury #MountainRetreat #PrivateHotTub #SkiAndStay #LuxurySTR

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.

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.

Zephyr Escape is a vibrant 3-bedroom retreat just minutes from Winter Park Resort. Enjoy two living rooms, arcade games, a gourmet kitchen, and a 6-person hot tub. Perfect for families, with ski slopes, tubing hills, and downtown fun all close by. Relax, play, and create unforgettable memories. #ZephyrEscape #WinterParkRetreat #FamilyVacation #SkiAndStay #HotTubLife #LuxurySTR

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