For many buyers, the dream of owning a home in the Florida Keys begins with an online search. But according to Sandy Tuttle, founder and owner of Island Welcome Real Estate, knowing you want to buy "somewhere in the Keys" is not enough. The four main submarkets—the Lower Keys, Marathon, the Upper Keys, and Key West—offer vastly different experiences, regulations, and trade-offs.
Marathon stands out for investment-minded buyers. It is the only community in Monroe County that allows weekly vacation rentals on any home, with no cap on licenses. This makes it a prime choice for generating rental income. "If someone is investment-minded and wants a better income return, we are absolutely going to suggest we explore Marathon," Tuttle said. However, the trade-off is a busier atmosphere with higher turnover and more visitors.
The Lower Keys, stretching from Big Pine Key to Key West, offer a quieter, more residential feel. Monroe County requires a 30-day minimum rental term in most unincorporated areas, reducing short-term turnover. "In the Lower Keys, you almost do not know which houses are rentals," Tuttle noted. Accessibility has improved with Key West International Airport offering direct flights from major cities, making it easy to reach. From anywhere in the Lower Keys, the airport is 40 to 45 minutes away.
The Upper Keys, anchored by Key Largo, are an extension of the Miami market. Proximity to Miami International Airport and Fort Lauderdale-Hollywood International attracts buyers seeking quick getaways. However, this comes with higher density and traffic. The buyer profile here tends to be those wanting a weekend escape rather than a permanent relocation.
Key West offers a vibrant mix of culture, nightlife, and walkability. Properties with short-term rental licenses exist but are rare and command premium prices. The city does not issue new licenses, making existing ones valuable.
Tuttle emphasizes that the right choice depends on individual priorities. Key questions include: What do you want your daily life to look like? Are you focused on boating or walkability? Do you want rental income, or is this for personal use? Answers typically point to one submarket. For maximum rental income, look at Marathon. For a laid-back, low-traffic neighborhood, choose the Lower Keys. For Miami access and weekend escapes, consider the Upper Keys.
"It is not one size fits all," Tuttle said. "Things vary quite a bit, and we have to focus on a case-by-case basis to really identify properties." Exploring the different communities across the Florida Keys is a useful first step, followed by consulting a local expert who knows each submarket intimately.
