Luxury Properties

Luxury Vacation Rentals in Winter Park CO

Looking to make unforgettable and enduring memories during your upcoming mountain getaway? Search no further, reserve one of our opulent Winter Park rentals today; providing guests with something extraordinary and distinctive that is bound to be unforgettable!  Stay Winter Park is delighted to offer a splendid array of vacation homes, town homes,  and condos that surpass your typical vacation rental with numerous additional touches and details to enhance your stay right from the beginning.

Our deluxe rentals are all recently built and showcase top-of-the-line appliances, granite countertops, private garages, flat screen HDTVs, and more! Many of these Winter Park rentals also boast their own private hot tub and a spacious deck with stunning mountain views. Some even feature large communal areas for group gatherings.  Numerous properties are conveniently situated near local attractions and activities,  while others are tucked away off the beaten path, providing guests with a sense of seclusion.

Moreover, several properties in this luxury collection are ideal for corporate or executive retreats, family  reunions, or weddings in Winter Park. We offer customized quotes for groups to accommodate your travel and event requirements, along with recommendations for local vendors offering additional services. Don't hesitate to reach to our Group Reservations team  today. We encourage you to secure a vacation of a lifetime at any of these luxurious properties, explore all the rentals in this collection, and prepare to embark on an unforgettable journey.

Search Other Popular Vacation Rental Categories:

Downtown Winter Park Rentals, Private Homes, Pet Friendly,  Winter Park Cabins, Base Village, Ski in Ski Out Lodging, Condo Complexes

Search Other Nearby Areas:

Fraser, Tabernash,  Winter Park Highlands,  Granby Ranch, Gore Pass




Properties Available 34 properties available
This tri-level townhome offers an abundance of natural light and generous square footage, making it the perfect vacation rental for families or individuals seeking spacious accommodations. The primary level features a spacious entryway adorned with tiled flooring, providing ample space for storing jackets and coats. This area also offers convenien
Hot HOT 14
Timber Lake 341
Timber Lake 341
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 9
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This 3-bedroom unit offers something for everyone, including pets, accommodating up to 9 persons with stunning views, open floor plan and a private outdoor hot tub. Situated in a convenient location at Grand Park, this townhome is truly wonderful.The primary floor features an expansive layout that includes the living, kitchen and dining spaces, cr
Hot HOT 13
228 Mountain Willow
228 Mountain Willow
Townhome - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 4.9 10
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The ski resort can be admired through the expansive windows and from the rooftop deck, while the vaulted ceilings enhance the spaciousness of the area. Relax on the comfortable sofas, watch TV or cozy up by the gas fireplace. The dining area and kitchen are conveniently located nearby, allowing the cook to engage with the group. The kitchen boasts
Hot HOT 12
Arrow at Winter Park Unit 248
Arrow at Winter Park Unit 248
Townhome -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 15
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Experience one of the finest vistas in Winter Park at this Arrow townhome. Spanning three levels, this tri-level residence is ideally situated on Main Street in downtown Winter Park, making it an excellent choice for your upcoming mountain getaway. The townhome boasts a generous 1,436 square feet of living space across four levels, featuring thre
Hot HOT 24
Arrow at Winter Park Unit 274
Arrow at Winter Park Unit 274
Townhome
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
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Indulge in an authentic luxury mountain getaway in this delightful townhome, ideally situated near the heart of downtown and adjacent to Vasquez Creek. This residence features breathtaking vistas and is conveniently located on the complimentary shuttle route to Winter Park Resort. It is also within walking distance of various downtown dining estab
Hot HOT 16
Townhome on Vasquez Creek #6
Townhome on Vasquez Creek #6
Townhome - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 27
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This residence in Colorado is situated 2/3 of a mile from the main street in downtown Winter Park and three miles from the Winter Park Resort, nestled in a charming neighborhood that provides a sense of seclusion along with stunning mountain vistas. It serves as an excellent setting for either a large family or a small group. The recently renovat
Hot HOT 10
40 Crescentview Lane
40 Crescentview Lane
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 4
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This luxurious Arrow townhome unit is an ideal choice for couples (and Pets!) seeking a relaxing getaway in downtown Winter Park. With 3 bedrooms, it can accommodate up to 10 guests, providing stunning views and a private hot tub for a truly memorable vacation experience.The lower level features a private garage with space for 2 cars parked in tand
Hot HOT 20
Arrow at Winter Park Unit 276
Arrow at Winter Park Unit 276
Townhome - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.7 4
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Experience a beautifully renovated cabin in the heart of downtown Fraser, offering all the amenities for an ideal family retreat. This location is conveniently within walking distance to various restaurants, breweries and shops. Additionally, the property is accessible via the complimentary town shuttle, providing effortless transportation to the
Hot HOT 33
133 Eisenhower
133 Eisenhower
Cabin -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 1
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This residence is ideally suited for several families or small groups seeking both privacy and a convenient location for their skiing or summer holiday. Notable features of this Winter Park home include stunning mountain views of the Continental Divide and Byers Peak, along with the added benefit of three master suites for enhanced privacy. We bel
Hot HOT 18
Leland Creek Home
Leland Creek Home
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 4.3 10
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The cozy and inviting interior of this pet-friendly home features hardwood floors, a stone fireplace, and plush carpeting in the open floor plan. The spacious kitchen boasts stainless steel appliances and granite countertops, while the dining room and living room provide ample space for your family to relax. Outside, the deck with a gas grill offe
Hot HOT 19
55 Campfire - Rendezvous
55 Campfire - Rendezvous
Private Vacation Home - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.8 17
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This vacation rental boasts an ultra-contemporary design and elegant furnishings, featuring 1,764 square feet of living space across two levels. Numerous expansive windows allow guests to admire the stunning mountain views. The expansive living room boasts a southern exposure, offering breathtaking views of stunning sunsets. It provides direct ac
Hot HOT 24
47 Lookout Point - Rendezvous
47 Lookout Point - Rendezvous
Private Vacation Home -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 10
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This residence is located in the serene residential area of Fraser, just 6 miles away from the Winter Park Ski Resort. Situated on a 0.8-acre lot, it offers convenient access to the free town shuttle, which stops right across the street.The property has been transformed into a luxurious, high-end themed vacation home, featuring 1,752 square feet of
Hot HOT 20
59 Jabberwocky Home
59 Jabberwocky Home
Private Vacation Home -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 11
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