Book direct with Southern Diversion Properties · No third-party booking fees
Islamorada · Key Largo · Marathon

Your own
Florida Keys.

Oceanfront stays with room to gather, space to unwind, and the water just beyond your door.

Explore our properties
Choose a property below
Tell us when you'd like to come
Personal help from our team
Send an inquiry  ↗
A small collection, thoughtfully kept

Room to come together. Space to find your own quiet.

From the Village of Islamorada to the open-water edge of Key Largo, each Southern Diversion home pairs privacy and generous outdoor living with the easy pleasures of the Keys. Tell us where you’d like to stay and when—we’ll help with the rest.

A celebration by the water

Your Dream Wedding, Where the Ocean Meets the Sky.

Explore Weddings & Events

Gather the people you love for a wedding weekend, an intimate celebration, or a special family occasion in the Florida Keys. Share your plans with us and we’ll discuss whether one of our private waterfront estates is a fit.

Choose your hideaway

Three ways to unwind.

Ask us directly about dates, rates, and your stay.

Beyond the front door

Three ways to find your Keys.

Local color, water views, and room to slow down.

One stay, many day trips

Explore more of the Keys.

Our three homes are about an hour apart, making it easy to enjoy the character of different islands during your stay. Wherever you settle in, consider a day on the water, a fishing charter, snorkeling or diving, a scenic drive along Overseas Highway, and a stop for local seafood or a sunset view.

Boating & fishingReef trips & divingWildlife & natureScenic drives & local dining
The feeling we hope you take home
“The best days here are the ones with nowhere else you need to be.”
Southern Diversion Properties · Florida Keys
Direct booking inquiry

Tell Terri what you’re planning.

Share your dates, group size, and a few details. Your inquiry will be sent directly to Terri Melilli.

Your inquiry will be sent securely to Terri Melilli.