Winter Park Lodging

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

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

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.

After a day of outdoor adventure, come home to relax on the large, comfortable leather sectional sofa surrounded by the luxury of the great room with vaulted ceilings, oversized windows, gas fireplace and 65" flat screen TV with sound bar. Set up a puzzle or board game on the lift-top coffee table from the wide selection of games, toys and books in this home. This room adjoins a fully equipped gourmet kitchen with granite countertops, new appliances, sizable pantry and spacious dining at the main table with additional seating at the large kitchen island or adjustable game table.

Experience the Pinnacle of Winter Park luxury. With jaw-dropping ski slope views, a private hot tub, designer interiors, and space for up to 15 guests, this 4BR retreat blends upscale comfort with unbeatable location—just 2 minutes from Winter Park Resort. Enjoy a chef’s kitchen, multiple living areas, expansive decks, and heated garage. Guests say, “We loved it so much, we changed our plans to stay longer!”

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

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

Modern luxury meets mountain ease at Stage Coach, a beautifully curated 4-bedroom, 3.5-bath retreat located just blocks from downtown Winter Park and surrounded by walkable trails, restaurants, and outdoor adventure. Whether you're here to hike, dine, bike, or unwind, this home offers everything you need for a premium, year-round mountain experience.

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

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