Downtown Winter Park

Vacation Rentals in Downtown Winter Park CO

Downtown Winter Park boasts a vibrant array of restaurants, shops and year-round activities for guests staying in a Winter Park vacation rental. Whether you choose to stay on Main Street or within a block, you'll have convenient access to all that the excitement in Downtown Winter Park!

Stay Winter Park offers a diverse selection of rentals from condos to luxury townhomes. In the summer, guests can enjoy music festivals at Rendezvous Event Center, art festivals, outdoor dining with live music and easy access to hiking and mountain biking trails. During the winter months, visitors can still savor local dining, visit the sledding hill and utilize the free town shuttle for transportation to the ski resort or the town of Fraser.

Excited to plan your getaway? Explore our inventory of downtown Winter Park vacation rentals below and easily book online using our reservation system. For inquiries or special requests, please reach out to our sales team for assistance in creating an unforgettable vacation experience!

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Private Homes, Winter Park Cabins, Base Village & Ski in Ski Out Vacation Rentals, Condo Complexes in Winter Park, Luxury Properties

167 properties available

On the second floor of the building, this 3 bedroom unit has 1,450 square feet and a 1 car garage. Please note there are a number of stairs to the unit and no elevator at the property.In this unit, the open living room has a wood paneled wall to accent the vaulted ceilings, comfortable furnishings and has some nice in room amenities that include a

Timber Run Cedar Unit 4

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A second floor unit with 806 square feet, this unit is comfortably furnished with 2 bedrooms and 1 full bathroom.Recently remodeled, the kitchen offers new appliances, cabinets and granite counter tops. The dining table is next to the kitchen area and has seating for 4 persons. Additional seating for 3 people is available at the breakfast bar.In t

Lion's Gate Pines Unit 113

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The well-lit condo with two bedrooms is situated on the ground floor of the building, providing convenient access and a brief stroll to the primary clubhouse and complimentary town shuttle stop.The recently completed kitchen is fully stocked with supplies, making it effortless to prepare meals or snacks. It features modern appliances, cabinets and

Beaver Village Unit #0711

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Kings Crossing 12 invites you to its unloading area at the entrance, which offers ample space for storing coats and boots. The indoor hot tub, conveniently located near the front door, provides a perfect way to unwind after a day of activities. This family-friendly townhome boasts an ideal location in downtown Winter Park close to a selection of re

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Kings Crossing Townhome 12

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Perfect for families looking for a homey feel in their vacation rental in this two bedroom two bathroom condo with a mountain theme with a personal touch.The solid hardwood flooring in dining room which will seat 4 to 6 people comfortably, for additional seating try using the kitchen counter that doubles as an extra eating place. The kitchen offer

HOT 11

Beaver Village Unit #0521

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This Winter Park family getaway offers a spacious and wonderful 2-bedroom accommodation. Situated on the ground floor of building 2, it provides convenient access to the free town shuttle and main clubhouse.This unit has undergone an amazing renovation, featuring hardwood flooring throughout the main open floor plan that perfectly complements the

HOT 11

Beaver Village Unit #0211

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This unit has two interior levels with 1,450 square feet encompassing 2 bedrooms plus a loft and 3 bathrooms with Wi-Fi access. The living room offers a gas fireplace with wood paneled accent wall, vaulted ceilings, TV with VCR, queen sofa sleeper and other comfortable furnishings to relax. No air conditioning.Adjacent to the living room, the dini

Timber Run Dogwood Unit 305

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This ground floor unit offers 1,450 square feet with Wi-Fi access and 3 bedrooms and 2 full bathrooms.In the main living room, wood exposed beams accent the southwestern decor. Guests will enjoy the TV, VCR, private balcony and queen sofa sleeper and free Wi-Fi access. No air conditioning.In a separate alcove area off the living room, there is a s

Timber Run Aspen Unit 2

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This charming studio unit is ideally situated in a prime downtown location, conveniently near various shops, restaurants, and year-round activities. The free town shuttle stops directly in front of the building, making it an excellent place to unwind after a day of outdoor enjoyment.The open floor layout features newly installed flooring across th

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Snowblaze Condos Building E Unit 102

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This one bedroom condo has a mountain theme accents with personal touches making for a perfect spot to rent for families or a couples.The solid hardwood flooring in the dining room which will seat 4 to 6 people comfortably, for additional seating try using the kitchen counter that doubles as an extra eating place. The kitchen offers lots of counte

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Beaver Village Unit #0521R

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This condominium features one bedroom, one bathroom and is equipped with all the necessary amenities. It is located on the second floor and includes a private deck with views of the Winter Park Resort. The kitchen is fully stocked with utensils, dishes, pots, pans, a coffee maker, microwave and has seating for two at the breakfast bar.The dining a

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Beaver Village Unit #0623R

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This beautifully appointed and expansive unit features two bedrooms, a loft and three bathrooms, situated on the sixth floor of the building. Ideal for families, this rental accommodates up to eight guests in beds and includes various amenities to enhance your comfort, such as a Pack-n-play crib, a game table suitable for cards or board games and a

HOT 13

Crestview Place Unit 607

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