Private aviation, boating, and vacation-rental-zoned waterfront property are shaping a different kind of luxury opportunity in Marathon
For decades, buying a home in the Florida Keys was largely a lifestyle decision: a place to keep the boat, escape winter, spend weekends on the water, and eventually pass down to the next generation.
But a different type of buyer is increasingly looking at the Keys through an investment lens. Instead of asking only, What will this property cost me to own? Sophisticated buyers are asking a more interesting question:
Can I put capital into an asset I actually want to own, use it when I choose, and operate it as a licensed vacation rental when I am somewhere else?
That question is particularly relevant in Marathon, where private aviation, direct boating access, a well-established vacation-rental market, and limited island real estate converge. One property currently on the market illustrates that idea particularly well.
At 2394 Coco Plum Drive in Marathon, Florida, an $11 million offering packages three neighboring luxury waterfront residences into a single acquisition, creating an unusual combination of personal-use real estate, licensed vacation-rental use, and waterfront lifestyle.
The New Luxury Isn’t Just a Second Home
For high-net-worth buyers, the traditional vacation-home equation can be inefficient. A multimillion-dollar residence may be used for several weeks or months each year while continuing to incur taxes, insurance, maintenance, and management expenses during the remainder.
Properties zoned for licensed vacation rental use change that equation. Rather than simply parking capital in a second residence, buyers can consider homes capable of serving two purposes: a residence for their own enjoyment and a property that can be legally rented to guests when they are away.
That distinction is particularly important in Marathon, Florida.
The City of Marathon has an established regulatory framework for licensed vacation rentals, including annual licensing requirements. Current city standards permit qualifying vacation rentals for stays between seven and 28 nights, subject to licensing and other requirements.
That creates a fundamentally different ownership proposition from markets where short-term rentals are prohibited or restricted to considerably longer stays. For buyers, the attraction isn’t simply owning a home in the Florida Keys. It’s owning an asset in a destination where vacation demand and luxury lifestyle intersect.
A Three-Residence Waterfront Portfolio
2394 Coco Plum Drive expands the concept into a rare three-residence portfolio.
The offering includes three designer homes built by D’Asign Source in 2019, totaling approximately 12,198 square feet and 18 bedrooms.
Each residence is about 4,066 square feet with six bedrooms, 6.5 bathrooms, furnished interiors, and spacious living areas.
Outside, each home features its own pool, tiki hut, and deep-water dock with direct ocean access, creating three fully independent waterfront vacation properties rather than a single estate.
Why Three Homes Can Be More Interesting Than One $11 Million Estate
At the ultra-luxury level, bigger isn’t always more flexible.
An $11 million single-family estate generally has one use at a time. The owner occupies it, rents the entire property, or leaves it vacant. Three neighboring residences create more possibilities. An owner could reserve one residence for personal use while operating the others as licensed vacation rentals. A multigenerational family could occupy all three while maintaining privacy between households. A company could use the collection as an executive retreat. A buyer could approach the properties as a luxury vacation-rental portfolio.
Or the entire collection could function as something increasingly difficult to recreate in the Florida Keys: a private waterfront compound consisting of multiple independent homes.
That optionality is part of the value. So is the fact that the homes already exist.
Building in the Florida Keys is fundamentally different from developing in many mainland markets. Available land is constrained, construction is highly regulated, and creating three neighboring waterfront residences with individual pools and dockage is not a simple proposition. For certain buyers, acquiring an existing collection can be more attractive than spending years attempting to recreate one.
Private Aviation Is Changing the Marathon Conversation
Accessibility has also become an increasingly important part of the luxury real estate equation. Florida Keys Marathon International Airport places private aviation directly in the Middle Keys, eliminating the need for many private travelers to land elsewhere and complete a lengthy drive to Marathon.
Now, the airport’s private-aviation offering is getting another luxury upgrade. Million Air Florida Keys is operating at Marathon International Airport, with a new facility planned. Million Air’s Marathon operation offers private aviation services from a centrally located airport with a 5,008-foot runway and substantial ramp space, positioning Marathon as a convenient private-aircraft gateway between Key Largo and Key West. For affluent homeowners traveling from South Florida and other major markets, that matters.
The value of a second home isn’t determined only by the house itself. Ease of access determines how often it gets used. A waterfront home that requires complicated travel logistics may become a once-or-twice-a-year destination. Private aviation into the same island community changes the equation.
Land the aircraft in Marathon, reach the residence within minutes, and trade the runway for the water. For a buyer who already organizes life around private aviation, boating, and multiple residences, that convenience can be more valuable than another bedroom or another thousand square feet.
In Marathon, the Boat May Matter as Much as the House
Luxury in the Florida Keys also operates differently from luxury in Miami, Palm Beach or Naples.
Here, the waterfront isn’t simply a view. It is infrastructure.
Dockage, water depth, bridge clearance, and access to open water can materially change how a property functions.
At Coco Plum, each residence has its own dock with deep-water, direct ocean access. That gives owners and guests the ability to move from the house to the Atlantic without treating boating as a separate excursion. Fishing, diving, sandbars and days on the water become part of daily life. That is an important distinction for buyers comparing luxury properties across South Florida. In the Keys, the pool may be beautiful. But for the serious boating buyer, the dock can be just as important as the house.
Tourism Gives the Investment Thesis a Real Economic Foundation
The lifestyle story would mean considerably less without underlying visitor demand.
Recent Florida Keys tourism data provides useful context.
In May 2026, Keys hotel occupancy reached 78.8%, up 4.9% year over year, while average daily rates climbed to $343.30. Revenue per available room increased 9.7% year over year.
Short-term rentals remained an important part of the destination’s accommodation market as well. Those numbers don’t indicate the performance of any individual vacation rental. Property quality, management, pricing, seasonality, operating expenses, and competition all matter. However, they demonstrate something important about the market:
The Florida Keys are not simply a collection of second homes. They are a tourism economy with sustained demand for places to stay. For an owner of a high-end vacation property, that context matters when weighing how a home might be used during the periods when it would otherwise sit closed.
Parking Capital Somewhere You Actually Want to Be
There is a broader shift among affluent real estate buyers. The question is no longer investment property versus lifestyle property, but whether one asset can serve as both.
An investor can place $11 million into a purely financial asset, or into a vacation home that stays closed for most of the year. Properties like Coco Plum sit between those extremes.
Owners gain waterfront living, private dockage, and personal use, while also having the option to operate within Marathon’s licensed vacation-rental framework.
This is not a passive or risk-free purchase. Buyers must evaluate expenses, insurance, management, taxes, licensing, and booking logistics. But it offers a clear alternative: a luxury home that does not have to sit closed when the owner is elsewhere.
An Asset That Doesn’t Have to Sit Empty
That may be the strongest case for flexible-use luxury real estate in the Florida Keys.
2394 Coco Plum Drive is not just three waterfront homes listed for $11 million. It is three assets in one: a luxury waterfront compound, a vacation-rental portfolio, and a private gateway to the Florida Keys. For some buyers, it can function as all three.
As private aviation in Marathon expands and luxury buyers look beyond traditional South Florida markets, the Middle Keys offer a clear proposition: own the destination, access it easily, enjoy it personally, and rent it to guests under a city license when you’re away.
For buyers who think about their real estate holdings in more than lifestyle terms, that may be a more interesting definition of a second home.
2394 Coco Plum Drive is currently offered at $11,000,000 in Marathon, Florida. The portfolio includes three residences totaling approximately 12,198 square feet and 18 bedrooms, with private pools, tiki huts, and deep-water dockage. The residences are zoned for weekly vacation rental use and are currently operating as licensed weekly rentals.
Additional property details, listing information, and the opportunity to learn more about 2394 Coco Plum Drive are available through kelseycaputorealtor.com.
