Winter Park Luxury Vacation Rentals

Explore Luxury Lodging 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, Pet Friendly, Base Village, Private Homes, Winter Park Cabins, Vacation Condos, Ski In Ski Out, Townhome Rentals

Search Other Nearby Areas:

Fraser, Tabernash, Winter Park Highlands, Granby, Grand Lake



Properties Available 46 properties available
This Bear Crossing town home has a very spacious interior, high-end finishes throughout and multi-level floor plan. The 2,000 square feet offers more than enough space for a group of eight to spread out and take advantage of the great outdoor activities nearby.A wonderful 3 bedroom 4 bathroom town home provides guests a feeling of seclusion but st
Hot HOT 16
Bear Crossing 845
Bear Crossing 845
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 8
View Property Details
This magnificent and authentic log cabin residence boasts a wonderful wrap-around deck with breathtaking mountain and lake views and in the evenings you can enjoy the pristine Colorado night skies with tons of stars, moon and more! Our home is on one private acre yet close to the outstanding town of Grand Lake and western entrance to Rocky Mountai
Hot HOT 14
1230 Columbine Dr
1230 Columbine Dr
Private Vacation Home
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
View Property Details
Escape to the mountains at this splendid, newly constructed residence boasting unforgettable mountain and lake views with a high-end interior designed 5 bedroom home that will sleep up to 10. This extraordinary mountain home offers beatle-kill hardwood flooring on the main level, accented by hand-hewn wooded plank ceilings and custom cabinetry.On
Hot HOT 12
128 GCR 4034
128 GCR 4034
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 6
View Property Details
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 15
Leland Creek Home
Leland Creek Home
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 4.5 16
View Property Details
This magnificent custom mountain residence boasts one of the finest locations, positioned on the 8th fairway of the acclaimed Pole Creek Golf Course, offering breathtaking views of Sheep Mountain and Indian Peaks. Our home serves as a luxurious mountain sanctuary nestled on two private acres, ensuring both seclusion and stunning vistas in every dir
Hot HOT 25
144 Rainbow - Fairways at Pole Creek
144 Rainbow - Fairways at Pole Creek
Private Vacation Home - Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 4
View Property Details
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 20
133 Eisenhower Cabin
133 Eisenhower Cabin
Cabin -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 7
View Property Details
This upscale townhome in Fraser provides a tranquil rental choice while remaining conveniently positioned close to a variety of outdoor activities accessible year-round. Located at the Cabins of Porcupine Ridge, this expansive 4-bedroom unit can host up to 10 guests, featuring an open floor plan, a private patio equipped with an outdoor hot tub, a
Hot HOT 22
220 Quill Way
220 Quill Way
Private Vacation Home -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.8 9
View Property Details
Explore our brand new exquisite 2-bedroom, 2-bathroom condominium located in the center of downtown Winter Park! This flawless residence showcases top-notch contemporary aesthetics and comes fully furnished, perfect for your own use or as a vacation rental. Conveniently located near the main street, this unit provides easy access to Winter Park's d
Arrow at Winter Park Unit 202
Arrow at Winter Park Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 37
View Property Details
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 15
59 Jabberwocky Home
59 Jabberwocky Home
Private Vacation Home -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 25
View Property Details
Indulge in the opulence of this expansive and beautiful residence, which has been recently built and offers numerous amenities for you and your family to relish a delightful vacation in Fraser. This includes breathtaking mountain views, a private patio, in-floor radiant heating and a heated garage for two vehicles. Our home can accommodate up to
Hot HOT 11
74 Alder Brook
74 Alder Brook
Private Vacation Home -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 5 48
View Property Details
This recently built townhome features a three-level interior, along with two private deck and patio spaces that allow residents to appreciate the verdant forest scenery. The contemporary interior design exudes a sense of privacy, while being conveniently located just 3 ½ blocks from the main street in downtown.The primary level features a one-car
Hot HOT 16
15 Saddle Horn Way - Rendezvous
15 Saddle Horn Way - Rendezvous
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 4
View Property Details
Book your next stay slopeside with us at this lovely split-level townhome at Base Camp. Guests will enjoy easy access to the slopes, private patio with mountain views, 3 bedrooms, large windows for viewing the surrounding outdoors and 1 car garage parking. Guests also have access to the clubhouse with paid amenities - there's something to do any t
Hot HOT 11
Base Camp Townhome #106
Base Camp Townhome #106
Townhome -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 5
View Property Details

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

Copyright © 2026 • Stay Winter Park

All Rights Reserved.