Trusted Montana Vacation Home Management
Welcome to Big Sky Estates, where elevated hospitality meets trusted Montana experience. As a Montana-based vacation home management company serving Big Sky, we help homeowners protect their investment, deliver exceptional guest stays, and feel confident their property is being cared for with professionalism and attention to detail.
Backed by proven short-term rental experience in the Montana market, our team brings a hands-on, high-touch approach to vacation home management. Through Payton O’Reilly’s work building and operating BozemanBnB, we have seen firsthand what it takes to run high-performing rentals, care for homes well, and create a seamless experience for both owners and guests.
Our Mission
Big Sky Estates was created for homeowners who want more than basic oversight. We provide full-service vacation home management designed to support well-run rentals, memorable guest experiences, and the kind of dependable property care owners can trust from afar.
We believe comfort, quality, and safety should define every stay. From thoughtful home presentation and responsive communication to operations, vendor coordination, and day-to-day oversight, our goal is to ensure each property is cared for to a high standard while giving owners confidence that their home and their investment are in good hands.
We are a family-first organization, and that perspective shapes how we approach hospitality. We know that for many guests, a trip to Big Sky is about time together, tradition, and lasting memories, and we take pride in helping create the kind of stay that brings people back year after year.
Meet the Team
Big Sky Estates was founded by Payton O’Reilly and Morgan Sturm, two hospitality-driven operators with a shared passion for vacation rentals, homeowner trust, and exceptional guest experiences. Together, they combine Montana market knowledge, business expertise, and hands-on operational experience to deliver a higher standard of vacation home management in Big Sky.
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Payton O'Reilly, co-founder of Big Sky Estates, brings a strong financial background and a deep connection to Montana’s hospitality industry. Born and raised in Montana, Payton is a Certified Public Accountant (CPA) and a former Big 4 consultant, giving him the expertise to optimize property performance, manage finances, and drive strategic growth. His analytical approach, combined with a passion for creating exceptional guest experiences, helps Big Sky Estates deliver top-tier service while maximizing returns for property owners.
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Morgan Sturm, co-founder of Big Sky Estates, brings a blend of hospitality, strategic business thinking, and hands-on operations to every property she manages. After starting her career in fast-paced, data-driven sales environments, she co-founded and scaled a short- and mid-term rental company and has spent the past three years actively operating vacation rentals. Originally from Roanoke, Virginia and a former Division I field hockey player at Miami University, she now lives in Bozeman, Montana. Morgan specializes in owner communication, systems, revenue support, and vendor coordination, and holds a Breezeway Safety certification that reflects her focus on property care and guest experience.