Jackson Hole Vacation Rentals

Annie Jackson, as the Managing Director, spearheads the committed and locally-based Outpost team, driven by a mission to deliver unparalleled service, attention, and respect to both guests and homeowners. The company takes immense pride in its distinctive culture, which places a paramount focus on prioritizing employees' well-being, motivating them to consistently exceed expectations in all their endeavors.

At Outpost, what began as a single home in 2014, has grown to be the premier vacation rental company in Jackson, voted Best Property Management Company for five consecutive years. Within their inventory of 250 properties (and counting) – a third of the professionally-managed homes in the area – Outpost strives to be a home base for everyone, from young couples saving up for a weekend away to ultra-luxe homes for discerning guests.

With the goal of always providing a best-in-class experience, Annie’s team values and nurtures partnerships within the Jackson Hole community, providing a tremendous benefit to guests and homeowners. From a partnership with JH Air that enables seamless delivery of lift tickets to facilitating gear rentals, organizing private chefs, and welcoming guests with their own coffee and handmade donut holes, Annie’s team provides the warmest welcome to every single guest.

Through its portfolio of local businesses, Outpost extends beyond vacation rentals to include cleaning, landscaping, snow removal, coffee roasting, catering, private chefs, and a cafe – brands that truly set them apart. While each business thrives on its own, they also support one another to ensure guests, homeowners, customers, clients, and partners all have a unique and memorable experience in Jackson Hole.