Isaac D. Pestana

Isaac is a passionate entrepreneur known for his integrity and pioneering excellence in the short-term rental market. As the founder of Good Stay, he has built a brand that redefines the vacation rental experience by delivering curated, consistent, and high-performing properties that blend luxury, comfort, and innovative design.

With a strong foundation in real estate brokerage and investment strategy, Isaac has led multi-million-dollar acquisitions and structured unique investor partnerships that generate both cash flow and long-term equity. His work is driven by a deep understanding of market dynamics, guest experience, and the power of smart design to drive ROI.

Isaac’s leadership style is rooted in creativity, boldness, vision, and hands-on execution. His diverse background—from property analysis, to group travel hosting, and deal structuring to furnishing and marketing vacation homes—equips him to create value at every step of the real estate lifecycle. Whether raising capital, managing renovations, or optimizing listings, Isaac consistently delivers results for investors and unforgettable stays for guests.