For buyers beginning their Florida Keys home search, the first question should not be about budget or bedrooms but about which part of the Keys they are actually looking for, according to Sandy Tuttle, founder and owner of Island Welcome Real Estate. With 22 years in the market, Tuttle emphasizes that the four main submarkets—the Lower Keys, Marathon, the Upper Keys, and Key West—are genuinely different places with distinct personalities, rules, and trade-offs.
Marathon stands out for investment-minded buyers because it is the only community in Monroe County that issues weekly vacation rental licenses to any home without a cap on the total number. “If someone is investment-minded and wants a better income return, we are absolutely going to suggest we explore Marathon,” Tuttle said. The trade-off is a higher volume of weekend visitors and more neighborhood turnover, creating a more active environment that appeals to some but not others.
The Lower Keys, stretching from Big Pine Key to Key West’s edge, retain an old Keys character with less traffic. Monroe County requires a 30-day minimum rental term in most unincorporated areas, so the Lower Keys lacks constant short-term rental turnover. “In the Lower Keys, you almost do not know which houses are rentals,” Tuttle said, noting that clientele tends to be couples staying for a month or two. Accessibility has improved with direct flights to Key West International Airport from multiple major cities, making the Lower Keys a convenient choice for those seeking a laid-back, residential feel.
The Upper Keys, anchored by Key Largo, function as an extension of the Miami market due to proximity to Miami International and Fort Lauderdale-Hollywood airports. This area captures high volumes of day-trippers and weekend visitors, resulting in more density and traffic. It suits buyers looking for a quick getaway from South Florida rather than a permanent relocation.
Key West offers a mix of opportunities with rich culture, nightlife, and walkability, but short-term rental licenses are limited and attached to properties, fetching premium prices. Tuttle guides buyers through a consistent set of questions: daily lifestyle preferences, boating interests, rental income goals, and retirement plans. “It is not one size fits all,” she said. Exploring the different communities across the Florida Keys is a useful first step, followed by connecting with a local expert who knows each submarket intimately.
