About Island Breeze Vacations


The tropical beauty of the Florida Keys captivated the owners of Island Breeze, David and Joanne Grego when they purchased a vacation home in Key Colony Beach in 2003—and they knew they had to live here!  After two years of transitioning from Indiana, they became full-time Keys residents.


With extensive experience in customer service, construction and leadership, the Gregos instill these values in their team to ensure every Island Breeze vacation rental exceeds expectations—always putting the customer’s best interests first.


Centrally located in Marathon, FL, Island Breeze Vacations offers premier vacation homes throughout Marathon and Key Colony Beach. Here’s a little more about our dedicated team and how we serve you.

Joanne Grego

Owner

Joanne Grego has been at the helm of Island Breeze Vacations since 2003, building the company from the ground up. Over the years, “Jo” has expanded both her portfolio and her talented team—and there’s no slowing down now! Looking for expert guidance on décor and furnishings for your new vacation rental investment? Check out La Casa Iguana to get a feel for her style!

Carly Herman

Reservationist

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

Vacation Rental Property Manager/Realtor

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.