This was the recurring "life" question I often thought about before I started my vacation rental business over a decade ago. Growing up in different resort communities and working in a family owned property management business, I became very familiar with the housing market and tourist trends. As an emerging entrepreneur, I was seeking different ways to invest my time, knowledge and skills in a career that was somewhat untraditional, flexible, and financially sustainable. At the same time, I was interested in becoming a homeowner within my local resort town, but did not want to feel constrained by the commitment to live there for years to come. This was the point of conflict that opened my eyes to the window of opportunity before me -the epiphany of starting a vacation rental business. In this moment, I knew this was investment that would afford me with time and income to pursue new learning opportunities and passions. Ten years later, the passive income generated from the vacation rental industry, led to a pathway of freedom - the freedom to organize my time and resources to simultaneously manage a successful business from any virtual location. My intention in writing this book is to share this message of freedom by illustrating practical and effective ways to start your own vacation rental business. As you read, you will encounter a variety of ideas to guide your success such as: - Jake Miller has over a decade of experience in the vacation rental industry. Owning multiple vacation homes that are each financially profitable, he has the freedom to pay for college, expand his business, travel, and give back to his communities through charitable foundations.