About Island Breeze Vacations

Welcome to Island Breeze Vacations

~ from Tiki (left), Reef (right) and our Vacation Rental team

You premier vacation rental property management company, centrally located in the heart of the Florida Keys, Marathon, FL.


With that said, we have increased our staff to better serve you as homeowners as well as enhance our guest experience: 

JoAnne "Jo" Grego: The BO$$ Lady - Need help with decor and furniture for your new Vacation Rental Investment Property? Take a look at Hook, Wine & Sinker and Casa Iguana to browse some of Jo's design skills.

Kasey: is Jo's assistant and our on-site property manager that will be taking guest calls, organizing the team for check-in’s, making sure you are notified when there is an issue and will be working with Jo to make your experience as homeowners as pleasant as we can. 

Sandy: as always is our "bada$$" booking agent: she is focused on making all the guest reservations. 

Crystal: is our marketing goddess, she joined our team in January of 2018 and is doing very well getting our properties in front of thousands of potential guests. She is also a licensed Realtor in the Florida Keys.

Jenn: Bookkeeper, the person you want to talk to about your owner statements down to the last cent.

Wendy: is going on year 2 with us and she is our weekend warrior; she is on deck every weekend to be sure that cleanings and guest arrivals go smoothly.

There are a lot of moving parts to this business and it looks like we have them all covered. Jo has the support of her exceptional team. Owners, you can take a few steps back and let our amazing team do what we have been trained to do.... take care of your homes and our guests together.

A little background on the Island Breeze Realty, LLC Boutique Brokerage: The scenic beauty of this chain of tropical islands has always fascinated the Island Breeze business owners, David Grego and JoAnne "Jo" Grego along with the vast array of water activities that they can enjoy year round. 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. It is actually funny that David Grego became a Broker with his own real estate company because in his construction days he was often annoyed by some of the pushy Realtors. The Gregos fully understand customer service, construction, leadership and always strive to do what is in the best interest of our 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!

Contact us at: [email protected]