Weekday Promo
Save 20% off 1+ nights: Use promo code MW20 at checkout
*Offer is valid on new online bookings when you book by May 19, 2026, for 1+ night stays from February 12–May 21, 2026. Cannot be combined with other offers. Other exclusions and restrictions may apply to select properties.
155 properties available
This Winter Park condo offers ample space and a variety of sleeping arrangements suitable for groups, families, couples and individuals. Situated on the 3rd floor of the Beaver Village Condominiums complex, this four bedroom three bathroom unit boasts vaulted ceilings that allow for plenty of natural light to fill the space.The open floor plan is
The Telemark townhomes offer opulent interior design and premium finishes that provide an exquisite retreat. Each unit is equipped with standard features such as four-panel interior alder doors and trim, pendant-style lighting and an energy efficient radiant heating system. Ideally situated in downtown Winter Park, these townhomes are in proximity
Perfect for families seeking a luxurious condominium located in the center of downtown. This updated and spacious unit features two bedrooms, a loft and three bathrooms, located on the sixth floor of the building which is accessible by elevator and can host up to six guests. The primary level of the unit boasts impressive vaulted ceilings in the m
This studio unit, encompassing 443 square feet, has been thoughtfully renovated and features new flooring and furnishings. Situated on the fifth floor, it offers stunning views of the Winter Park Resort and is conveniently located just a 150-yard walk from the slopes and the village. The kitchenette is equipped with granite countertops and stainles
This lovely remodeled 2 bedroom condo offers guests a wonderful spot to enjoy a family vacation in Winter Park. The open floor plan offers vaulted ceilings, hardwood flooring except for the kitchen area which has slate tile flooring. The kitchen is equipped with new stainless steel appliances, light wood cabinetry and a small kitchen island that
This expansive two-level townhome is conveniently located just a short walk from downtown Winter Park, where visitors can enjoy a selection of restaurants and diverse shopping options. The interior is tastefully adorned with modern upgrades, making it an excellent choice for a vacation rental. The entrance to the townhome features a spacious coat
Welcome to your cozy mountain retreat at Timber Fox Building C Unit 3404, nestled in the heart of Winter Park. This luxurious 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and elegance, ideal for families or groups of friends seeking a memorable getaway.Step inside to discover a thoughtfully designed living space, complete with a mo
The renovated kitchen features tiled flooring, modern appliances, and updated cabinets and countertops. The compact center island serves as an excellent workspace or additional seating areas during meals. The unit is located on the ground floor, providing convenient access to the outdoor space.The dining area, located next to the kitchen, offers an
This condominium features two bedrooms and two bathrooms, encompassing a total area of 950 square feet. It boasts an open floor plan, enhanced by newer carpeting throughout and a modern kitchen equipped with stainless steel appliances. Located on the third floor, this unit does not have elevator access; the elevator services only the parking level
A genuine rustic cabin in the woods! This cabin, built in 1961, has undergone some updates and provides a private retreat featuring 3 bedrooms, 2 covered decks that showcase views of the forest and mountains, along with 2 interior levels that offer space for the family to unwind and enjoy a stylish escape from daily life.The primary level of the c
This cozy retreat is perfect for small families, couples or solo travelers. The fully equipped kitchen, featuring a stove, microwave, fridge, pots, pans and cooking utensils, allows for easy meal preparation. The spacious dining area connected to the kitchen and main living space, provides a comfortable setting for enjoying meals together.During c
Experience a stay in this exquisite three bedroom private townhome, where you can relish being close to the center of the vibrant downtown area filled with numerous activities. This residence offers an abundance of features, including a generous floor plan that accommodates up to 6 guests and a private outdoor hot tub for your enjoyment.The main e
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