Skyler Davis

Skyler is the data engine behind the success of the Five Star Properties portfolio. He analyzes competitive sets, local demand, market trends, seasonality, and dynamic pricing to ensure every home achieves top ADR and strong occupancy year-round.

His background in short-term rental revenue analytics — combined with his role as a licensed real estate agent specializing in short-term rental and cash-flow investment properties — makes him one of the most unique and valuable STR pricing strategists in the region. His real estate expertise allows him to evaluate properties not only from a revenue standpoint, but also from an acquisition, positioning, and long-term performance perspective.

Beyond revenue optimization, Skyler plays a key role in Five Star’s Estate Management and Home Watch programs, helping tailor service plans for high-value homes and absentee owners. He also assists with new client relationships, working closely with prospective owners to evaluate performance potential, explain strategy, and guide them through the onboarding process.

Skyler’s ability to blend data-driven decision making, real estate expertise, and client-facing communication helps ensure every owner partnership is built on transparency, performance, and long-term success.