Jason Caraway


Island Sky Investments is a private equity firm specializing in luxury vacation and resort-style real estate. We invest in ground-up development and the acquisition of existing properties in both the United States and foreign tropical destinations, offering our clients a comprehensive range of opportunities.

These investments involve specialized skills, knowledge, and a strong team. We are a team of experienced professionals with a strong understanding of real estate and finance. We utilize our expertise to evaluate and rigorously pursue only the most promising opportunities.

“At Island Sky Investments, our core values of honesty, integrity, and transparency serve as the foundation of our decision-making process and guide the choices we make as a company. We are committed to operating with the highest ethical standards, and building long-lasting relationships based on trust with our clients and partners.”