Rentals in Downtown Winter Park
Downtown Winter Park is a great hub of restaurants, shops and year-round activities that you can explore. You can stay right on Main Street or within 1 block for easy access to all that is happening! Stay Winter Park offers a large variety of rentals ranging from condos to luxury townhomes.
During the summer months, enjoy the music festivals at Rendezvous Event Center, art festivals and outdoor dining with live free music and easy access to a number of hiking and mountain biking trails. For the winter months, you can still enjoy the local dining, sledding hill and the free town shuttle can provide transportation to the ski resort or the town of Fraser.
Can't wait to book your getaway? Browse our inventory of downtown Winter Park vacation rentals below and book online with our easy reservation system. Please contact our sales team with any questions or for special requests to help make your vacation unforgettable!
This 2 bedroom vacation condo is on the third floor of the building with some interior updates to the living room and kitchen. Other amenities include in-room Wi-Fi, fireplace, full bathroom and clubhouse amenities.
This premium 3 bedroom unit is located on the first floor and offers an open floor plan in the main room, large flat screen TV, large kitchen, private deck and plenty of beds for everyone in the party.
This platinum rated 3 bedroom condo rental is on the second floor of the building and offers hardwood flooring, updated kitchen, comfortable furnishings throughout and refurbished bathrooms.
This Winter Park ski condo is on the 3rd floor of the building, an upper corner location offers peace and quiet, private balcony, full kitchen, large living room with fireplace and 3 bedrooms.
This condo rental for skiing in Winter Park is a ground floor condo, has 2 bedrooms, 2 bathrooms, ground floor entrance, full kitchen, fireplace and is close to the main recreation center on the property.
Upscale 4 bedroom town home rental within walking distance of downtown Winter Park and great amenities including private deck with mountain and rivers views, private outdoor hot tub, garage parking and lush interior design.
A perfect location on Main Street in downtown Winter Park, this 2 bedroom condo rental has deluxe interior design, large open kitchen and high end finishes throughout.
The 2 bedroom 1 bathroom unit has been recently renovated and has 651 square feet of living space with hardwood flooring throughout and carpet in the bedrooms. In the living room, a flat screen HDTV, wood burning fireplace, free in unit Wi-Fi access with a comfortable sectional sofa make this area a nice relaxing getaway.
Exclusive extras abound in this newly constructed end-unit at Arrow. Tip-top views from the hot tub with the Continental Divide and luxurious interior design for the wonderful 5 bedroom in downtown Winter Park.
Hi Country Haus 1 bedroom, 1.5 bath condo located in downtown Winter Park. Relax into this updated living area’s large sectional sofa with flat screen TV with gad fireplace, large open floor plan and private balcony.