StayWinterPark Memorial Day Escapes
Book your Memorial Day lodging today!
The kick off for the summer season is finally here.
So many vacation rentals to pick from - use our quick links below to book a great holiday weekend - condos, cabins or private homes. Check out pet friendly rentals too!
All our rentals are close to the great outdoors and provide the perfect spot to relax and enjoy!
126 properties available
Wonderful, spacious 2-bedroom family getaway in Winter Park. This ground floor unit is in building 2 providing easy access the free town shuttle and main clubhouse.Incredible remodel in this unit with hardwood flooring throughout main open floor plan to compliment the large sectional sofa (can also be used for additional sleeping with the sofa sle
Located on 3rd floor for extra peace and quiet, this cozy 2 bedroom has vaulted ceilings to allow for extra light in the living area with comfortable furnishing to enjoy a game, movie or your favorite TV shows on the flat screen TV or the ambience of the gas fireplace. A private deck has views of the Winter Park Ski Resort to enjoy. No air condit
Beautiful and spacious pet friendly 3 bedroom unit right from the heart of downtown Winter Park, this Trailhead Lodge unit has a wonderful view off the back deck of the Winter Park Ski Resort and downtown area of Winter Park a great place to drink morning coffee, outdoor dining area or a great spot to enjoy the evening sunsets.Families or small gro
A wonderful vacation rental that feels like a home away from home with its distinct lodge feel with rich wood and plush furnishings in the main living area. Relax and enjoy the flat screen TV and gas fireplace – perfect for a cozy evening. Guest can also access the private deck from this room to enjoy the forested view off the second floor of the
The condo has a distinctive warm feel which everyone will enjoy and all the comforts of home and completed renovated! A nicely updated kitchen with newer cabinets, appliances and counter tops. The dining area will comfortably seat up to 6 persons and is included within the open floor plan of the main room. In the living room, new furnishings all
This spacious townhome offers 1596 square feet on two levels and is Pet Friendly! The main level has vaulted ceilings with ceiling fans and the look of a true log cabin in the open floor plan encompassing the living, dining and kitchen areas. A gourmet kitchen offers stainless steel appliances, granite counter tops, solid wood cabinets and extra s
A wonderfully spacious condominium located just off Main Street in downtown Winter Park, you can enjoy a mountain view and walk to shops, restaurants, outdoor activities and events.Nickname the Moose Haven for its mountain outdoor themed décor that compliments a complete remodel making it an ideal vacation rental for families. The recently updated
A large kitchen has new counter tops, wood cabinets and appliances with breakfast bar. In the dining area additional seating for up to 4. Comfortable sofas are wonderful to relax in the living room to enjoy the flat screen TV, gas fireplace and view of the Winter Park Resort from the private deck. No air conditioning. A lovely, spacious and rem
Tons of light and a lot of square footage in this tri-level town home make it the ideal vacation rental for families or singles looking for lodging that has a lot of space.The main level has a large entryway with tiled flooring to storage your jackets, coats and an excellent spot to access the one car garage, laundry room and bedroom with 2 twin be
This cozy 1 bedroom condo has 607 square feet, on the ground floor level of the building and provides great access to the main clubhouse being across the parking lot from it and also the free town shuttle stop.In the living room an open floor plan encompasses the updated furnishing for a relaxing spot to enjoy the fireplace and mountain views. A f
This charming pet-friendly 3-bedroom retreat offers a cozy getaway for up to 8 guests and easy access to downtown Fraser's breweries, restaurants and great year round outdoor activities. A single level condo featuring an open floor plan with a fully equipped kitchen, breakfast bar, dining area, and a comfortable living room with a gas fireplace and
Located in the quiet residential neighborhood of Fraser, this home is 6 miles from the Winter Park Ski Resort and the home is situated on a 0.8-acre lot and provides easy access to the free town shuttle that stops across the street. This vacation getaway has been renovated into a luxurious, high-end themed vacation home with comforts and entertain
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