Downtown Winter Park

Vacation Rentals in Downtown Winter Park CO

Downtown Winter Park is a great hub of restaurants, shops and year-round activities that you can explore while staying in your Winter Park Vacation Rental. You can stay right on Main Street or within 1 block for easy access to all that is happening in Downtown Winter Park! 

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!


Properties Available 161 properties available
A retro 1 bedroom condo offers a comfortable rental spot with a private balcony, ground floor of the building for easy access for parking and taking the free shuttle.In the main living room, relax in front of the gas fireplace, TV with VCR, queen sofa sleeper and coat closet. No air conditioning.At the end of the main room, a dining area has table
Hi Country Haus Unit 2501
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.4 7
The main floor of the unit has high vaulted ceilings in the living room area with a modern furnished decor, gas fireplace, flat screen TV, free in unit Wi-Fi access, and access to the private 5th floor balcony will allow you overlooks downtown Winter Park and mountain views.Adjacent to the main living area, the dining room is on an elevated level w
Hot HOT 15
Crestview Place Unit 507
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.5 22
Guests will be sure to enjoy the beautifully updated kitchen with stainless steel appliances, granite counter tops, new hardwood flooring, cabinetry and is completely stocked with cookware, dishes and utensils for making great meals during your stay.Vaulted ceilings give the feeling of a lot of space in the main living area and the views of Winter
Hot HOT 11
Beaver Village Unit #2032
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.6 9
Discover our new stunning 2-bedroom, 2-bathroom condo in the heart of downtown Winter Park! This immaculate unit features high-quality modern design and is offered fully furnished, ready for your enjoyment or as a vacation rental. Situated just off the main street, you'll have easy access to Winter Park's dining and entertainment. With 9-1/2 ft cei
Hot HOT 15
Arrow at Winter Park Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 3
A great spot for couples (and Pets) wanting to take a break and enjoy downtown Winter Park luxury accommodations in the Arrow Townhomes. This unit will sleep up to 10 people in this 3 bedroom unit and it offers the best views with a private hot tub amenity for your next Winter Park vacation.A private garage where 2 cars can be parked in tandem is
Hot HOT 15
Arrow at Winter Park Unit 276
Townhome - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.7 4
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
Beaver Village Unit #0211
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 2
In the living room, the fireplace is perfect for cool evenings during the summer or winter. Check out the books in the owner’s library tucked along the wall, great for days you just want to stay inside and read a book or a movie on the flat screen TV. Guest can access the private patio from the living area as well and there is a queen sofa sleeper
Hot HOT 10
Beaver Village Unit #0711R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 2
A small family, couples or singles really enjoy this home away from home with a full kitchen complete with stove, microwave, fridge, pots, pans and cooking utensils are included making it easy to prepare meals or snacks. The large dining table is in the area adjacent to the kitchen and open to the main living area.A gas fireplace is inviting on coo
Hot HOT 10
Beaver Village Unit #0712
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 2
The main living room area offers comfortable chairs and sofas to relax and enjoy the gas fireplace, flat screen TV, DVD and Blue Ray disk player. The queen sofa sleeper offers an additional sleeping area. No air conditioning.In the dining room that overlooks the living room, there is seating for 8 persons to enjoy breakfast, lunch and dinner.Adjac
Lion's Gate Pines Unit 107
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
In the main living room of the unit, large comfortable furnishings compliment a wood paneled accent wall, TV, VCR/DVD, gas fireplace, free in unit Wi-Fi access, queen sofa sleeper and no air conditioning. The dining area provides guests access the private balcony with wonderful mountain views and the large table offers seating for 8 persons.A full
Timber Run Cedar Unit 3
Condo
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
A spacious unit 1,128 square feet, this 3-bedroom condo is on the second floor of the building and offers free Wi-Fi access. In the living room, the decor has a country theme and gas fireplace, flat screen TV, DVD, Blue Ray disk player and telephone. No air conditioning. A solid wood table and chairs in the dining area provide seating for 8 people
Lion's Gate Pines Unit 109
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
The condo has recently gotten a remodeled kitchen with new wood cabinets, tiled flooring, counter tops and stainless steel appliances. In the dining area there is a cozy spot for up to 6 persons and is encompassed within the open floor plan to be engaged with all of the activities. The living room has comfortable seating, a sofa sleeper if there
Beaver Village Unit #1812
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 6

Tell us what you're looking for and someone will contact you with available options.

By providing your phone number, you agree to receive text messages from our company. Message and data rates may apply. Message frequency varies.
I agree