Only 10 Properties
Your home is never buried in a large corporate portfolio.
Founder-led flat-fee luxury management
Full-service vacation rental management for a predictable $3,000 flat monthly fee. No percentage commissions. No cutting corners. Just a dedicated on-mountain team capped at 10 premium properties.
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Compare a traditional percentage-based management commission against Five Star Big Sky's flat annual fee.
Exclusivity
Five Star intentionally limits its Big Sky portfolio to exactly 10 premium properties so every owner receives direct attention, disciplined oversight, and a higher standard of care.
This is not discounted management. It is selective management. A smaller portfolio protects the time, communication, and accountability required to maximize performance while protecting the physical asset.
Your home is never buried in a large corporate portfolio.
You work with leadership, not a rotating support queue.
Fewer homes means stronger accountability and more consistent care.
We are built to be the most focused, not the biggest.

Our Services
One accountable team. One predictable fee. One uncompromising operating standard.
Pricing, channel mix, direct booking strategy, and reporting.
Responsive communication, arrival readiness, stay support, and issue resolution.
Turn readiness, vendor coordination, preventative checks, and owner peace of mind.
Transparent reporting, direct access, vendor accountability, and asset stewardship.
If we do not deliver on either side of our service - vacation rental management or asset management - we will make it right. If you are still not satisfied, we will refund up to that month's $1,500 fee for the service that missed the mark.
Our Team
A remote algorithm cannot protect your home during a winter freeze. You need experienced leadership, a trusted local partner, and a dependable on-mountain team.

Founder
Paul brings decades of hospitality and vacation rental leadership, including executive oversight in Big Sky. He leads pricing strategy, revenue optimization, owner communication, and the flat-fee model.

Local Partner & Property Manager
A licensed Montana property manager, Siobhan brings luxury portfolio experience, design sensibility, and trusted relationships with owners and vendors.

Meet the Founder
My career in vacation rental management began in Key West in 1999, when I founded and built my first management company from the ground up. What started with zero properties grew to 66 vacation rentals before I sold the business in 2007.
Since then, I have spent more than 25 years leading vacation rental, resort, and luxury residential operations. I helped launch residential operations at the Yellowstone Club, oversaw lodging operations for more than 1,500 units at Sunriver Resort, and managed portfolios of nearly 300 homes in Big Sky. Most recently, I served as General Manager for two of Big Sky's largest vacation rental management companies.
Throughout my career, I have developed deep experience in hospitality operations, revenue management, financial performance, owner relations, and the long-term care of valuable real estate assets. I have also seen firsthand where the traditional property management model falls short - particularly when rapid growth, corporate turnover, and high commissions begin taking priority over the homeowner.
I created Five Star Big Sky to offer something better: experienced, highly personal management built around stewardship, transparency, and measurable financial performance.
A Better Model
We do not believe homeowners should automatically surrender 25% to 40% of their rental revenue simply because that has become the industry standard.
Five Star Big Sky offers an alternative: a flat-fee management model designed for high-performing vacation homes. For properties generating $200,000 or more in annual rental revenue, this structure can put tens of thousands of dollars back into the owner's account each year.
But our difference goes far beyond the fee.
Large management companies are often focused on adding more inventory. General managers and property managers come and go, homes are passed between team members, and owners can begin to feel like property numbers rather than clients. Five Star Big Sky was intentionally designed to operate differently.
We manage only 10 select homes. This allows us to maintain a laser focus on every property, every guest experience, and every owner relationship. Each home is supported by an established local property manager with more than a decade of Big Sky experience and a trusted housekeeping team known for exceptional standards and meticulous attention to detail.
When you select Five Star Big Sky, you become part of a small, carefully managed collection backed by decades of experience in vacation rental management, hospitality, revenue strategy, financial performance, and asset management.
Everything we do is guided by one defining principle: stewardship. We are entrusted with your home, your guest experience, and the performance of your investment - and we take that responsibility personally.
Request a free revenue and savings assessment to see exactly how much profit you may be leaving on the table under your current commission structure.