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Short Term Rental Winter
January 22-23, 2026
JW Marriott Miami TurnberryAventura, FL

Michael Friedman
CEO at Simple Life Rentals
Speaker

Profile

Michael Friedman is a nationally recognized leader in the vacation rental and hospitality industry, currently serving as CEO of Simple Life Hospitality, a rapidly growing, Wisconsin-based property management company operating across key Midwest markets. With over a decade of experience building brands at the intersection of travel, real estate, and technology, Michael has become a trusted voice on topics ranging from revenue optimization and operational scale to homeowner engagement and AI integration.

As a former senior executive at Onefinestay and a current board member of both Vacation Rental University (VRU) and VRNation’s Education Committee, Michael brings a unique blend of high-touch luxury hospitality experience and cutting-edge short-term rental innovation. Under his leadership, Simple Life Hospitality has doubled down on its foundational “3 Cs” — Cash, Care, and Communication — while pioneering partnerships with platforms like Airbnb, Expedia, and Booking.com, and leveraging tools like dynamic pricing, predictive AI, and noise monitoring for both guest satisfaction and portfolio performance.

Michael is a sought-after speaker, consultant, and dealmaker—currently leading acquisition negotiations, developing franchise-alternative growth models, and mentoring a new generation of property managers across the U.S. He’s also known for weaving personal stories of gratitude, family, and legacy into his professional journey, offering audiences both practical insight and heartfelt perspective.

Whether he's guiding a room of investors, educating operators at a national summit, or reflecting on leadership with fellow CEOs, Michael’s message is grounded in value creation, relationship-building, and a relentless pursuit of excellence in hospitality.