The 5 Best Vacation Rental Companies Around Grand County

Whether it’s a ski getaway in Winter Park or a lakeside weekend in Grand Lake, the short-term rental scene in Grand County has become a key part of the local travel economy. But managing a vacation home at 9,000 feet is no small feat. From frozen pipes to late-night check-ins, it takes an experienced team to deliver both property protection and guest satisfaction. The companies featured in this year’s Best of Grand contest make it all look easy — offering local knowledge, real-time support, and homes that keep visitors coming back season after season.

SkyRun Vacation Rentals

SkyRun Vacation Rentals brings a hybrid model to the market: the power of a national brand paired with a locally owned Winter Park office. Their services include 24/7 guest support, dynamic pricing tools, homeowner dashboards, and flexible management plans. SkyRun promotes no long-term contracts and an owner-first mindset, allowing property owners to customize their level of involvement. With a portfolio ranging from slope-side condos to luxury homes, they focus on tech-enabled service without losing the personal touch.

Grand Mountain Rentals

Grand Mountain Rentals has been a Grand Lake mainstay for over 30 years, offering homes, cabins, and condos throughout the area. Their team emphasizes customer service and hands-on reservation support, with booking handled directly through their office or website. The company’s Facebook page showcases seasonal specials and insider tips, giving guests a friendly intro to the Grand Lake experience. Their longevity and consistent visibility in the community speak to a business that’s built to last — and trusted by both guests and homeowners alike.

Winter Park Escapes

Winter Park Escapes curates a broad collection of mountain-modern homes, ski condos, and luxury retreats, all with a heavy focus on guest experience and visual marketing. Their listings feature professional photography, virtual tours, and detailed amenity breakdowns, while homeowners benefit from revenue management tools and direct booking strategies. The site also promotes concierge offerings — everything from grocery delivery to outdoor equipment rentals — positioning Winter Park Escapes as both a lodging provider and a hospitality brand.

Stay Winter Park

Stay Winter Park is one of the largest vacation rental providers in the Fraser Valley, with a portfolio that spans condos, townhomes, and private homes. The company offers full-service management that includes housekeeping, maintenance, front desk service, and marketing. Their site highlights real-time availability, pet-friendly options, and seasonal deals. For property owners, Stay Winter Park provides detailed performance reporting and broad platform distribution, including Airbnb, Vrbo, and their own high-traffic site.

Winter Park Lodging Co.

Winter Park Lodging Co. promotes itself as a locally owned and operated company with a focus on personalized service for both guests and homeowners. Their offerings include premium bedding, curated welcome gifts, and real-time guest communication through text and app-based platforms. For property owners, they emphasize transparent reporting, dynamic pricing, and a team-based approach to care. Their site showcases a strong visual brand and guest-first design, which mirrors their full-service philosophy.

Thanks, ChatGPT.