Get to know us

Leo and Ella, a dedicated family-owned property investment firm, specialize in holiday homes and short-term vacation rentals. Their mission is to provide clients with the foundation to create lifelong memories while offering the opportunity to own holiday homes in unique locations that beautifully blend history, culture, and distinctive lifestyle benefits.

a narrow alley way with a bed on a balcony
a narrow alley way with a bed on a balcony

Our mission

We're on a mission to change the way the housing market works. Rather than offering one service or another, we want to combine as many and make our clients' lives easy and carefree. Our goal is to match our clients with the perfect properties that fit their tastes, needs, and budgets.

Our vision

We want to live in a world where people can buy homes that match their needs rather than having to find a compromise and settle on the second-best option. That's why we take a lot of time and care in getting to know our clients from the moment they reach out to us and ask for our help.

white and gray concrete house under blue sky during daytime
white and gray concrete house under blue sky during daytime
Bobby Caldwell

CEO/Owner

Hello, my name is Bobby Caldwell, the CEO and Owner of Leo and Ella, LLC. For 15 years, I managed operations for a major Fortune 500 retail company in the United States, overseeing millions of dollars in assets and driving significant profitability for the company’s bottom line. In 2021, I decided to combine my passion for travel with my business acumen gained over a 15-year career and embark on my own entrepreneurial journey. With this vision, I opened Leo and Ella, a property investment firm focused on emerging markets within the tourism industry, particularly in Puglia, Italy. My personal experiences owning and purchasing a family holiday home in Puglia inspired me to share the unique lifestyle and investment opportunities that this region offers with others.