Most buyers begin their Florida Keys home search online, but according to Sandy Tuttle, founder and owner of Island Welcome Real Estate, knowing you want to buy "somewhere in the Keys" is not a useful starting point. 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.
For investment-minded buyers, Marathon stands out as the only community in Monroe County that issues weekly vacation rental licenses to any home without a cap on total licenses. "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 higher volume of visitors and a more active environment, which may not suit buyers seeking tranquility.
In contrast, the Lower Keys, stretching from Big Pine Key to Key West, offer old Keys character with less traffic. Monroe County requires a 30-day minimum rental term in most unincorporated areas, reducing turnover. "In the Lower Keys, you almost do not know which houses are rentals," Tuttle noted, as clientele tend to stay longer and treat homes respectfully. Accessibility has improved with direct flights to Key West International Airport from major cities, making the Lower Keys a convenient retreat. The airport is no more than 40 to 45 minutes away by car.
The Upper Keys, anchored by Key Largo, function as an extension of the Miami market. Proximity to Miami International Airport and Fort Lauderdale-Hollywood International attracts buyers seeking quick getaways, but also brings higher density and traffic. Key West offers a vibrant mix of culture, nightlife, and walkability, with limited short-term rental licenses that command premium prices when available.
Tuttle advises buyers to consider daily lifestyle, boating needs, rental income goals, and long-term plans. "It is not one size fits all," she 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.
