Founder, The Dream Rentals
Sebastian founded The Dream Rentals with a simple idea: vacation homes should feel even better in person than they do online. With a focus on luxury properties and group-friendly spaces, Sebastian approaches hosting with care, attention to detail, and respect for the guest experience. From clear communication to thoughtfully prepared homes, every stay is designed to feel welcoming, seamless, and memorable.
Co-Founder & Partner, The Dream Rentals
Josh brings deep expertise in risk management and financial operations, gained from a decade of experience in commercial insurance brokerage at a top-three wholesale brokerage in the country. As Partner, he oversees all financial modeling, property launches, and strategic scaling initiatives. He has spearheaded creative property acquisitions and identified key strategic partners along the way. His analytical mindset and operational excellence were instrumental in navigating The Dream Rentals through rapid growth during COVID-19 and beyond. Josh ensures every property launch meets exacting standards, and that every financial strategy and growth project is meticulously planned and executed, maintaining the boutique service quality of The Dream Rentals.
Sebastian has talked through how we built the business on Straight Up Chicago Investor (episode 389).
Markets with homes today: Chicago (core), Forest Park, Skokie, Kansas City , Minneapolis , Jeffersonville, IN (Louisville area).
Beyond the Midwest: Texas, Arizona, Maryland, Florida, Montana, South Dakota, Los Cabos.
Cleaning is handled by our own company, Dream Cleaning.
