About Island Breeze Vacations
The scenic beauty of this chain of tropical islands has always fascinated the Island Breeze business owners, David Grego and JoAnne Grego. After purchasing a vacation home around 2003 in Key Colony Beach, they knew instantly that they had to live here. It took two years to restructure their responsibilities in Indiana before they could become full-time Florida Keys residents.
The Grego’s fully understand customer service, construction, leadership and always strive to do what is in the best interest of the customer. They have instilled these values in their team members and trust your experience in an Island Breeze vacation rental home will be nothing short of excellent!
Island Breeze Vacations is here to provide premier vacation rental properties in Marathon, Sombrero Beach and Key Colony Beach. We are centrally located in the heart of the Florida Keys, in Marathon, FL. In order to better serve you, we’d like to tell you a little bit about our team.
Joanne Grego
Joanne Grego has owned Island Breeze Vacations and built the company from the ground up starting in 2003. Over the years “Jo” has grown both her portfolio and her team, and watch out because there’s no stopping us now! Need help with decor and furniture for your new Vacation Rental Investment? Take a look at Rest-A-Shore and Casa Iguana to get a feel for her style.
Carly Herman
Reservations Coordinator
Since 2016, Carly has helped connect people with the perfect home — first in real estate and now as a dedicated booking agent. She brings that same attention to detail and client-focused care to vacation planning. Carly is here to make booking your Keys escape simple and stress-free.
Kristina Boswell
Kristina is a trusted Realtor and vacation rental property manager based in Marathon, Florida. With a deep appreciation for island living and a strong understanding of the local market, Kristina specializes in helping clients buy and sell homes while also managing short-term rental properties. She offers full-service property management, including guest communication, maintenance coordination and rental income optimization. Whether you’re looking for your dream home in the Keys or need a dependable professional to manage your investment property, Kristina brings local insight, dedication and a personal touch to every client relationship.
As you may have begun to realize, there are a lot of moving parts to this business which is why Jo has pulled together the support of an exceptional team. The service that we offer allows owners to take a few steps back and let our amazing team do what we do best: book these home and ensure guests have a positive experience that will encourage them to return for years to come.
Contact us at: [email protected]