Most buyers start their Florida Keys home search online, but according to Sandy Tuttle, founder/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.
Marathon stands out for investment-minded buyers. It is the only community in Monroe County that issues weekly vacation rental licenses to any home without a cap on the total number of licenses. "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 atmosphere: Marathon experiences higher visitor volume and more neighborhood turnover, which appeals to some but deters others seeking tranquility.
The Lower Keys, spanning 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 constant short-term guest turnover. "In the Lower Keys, you almost do not know which houses are rentals," Tuttle said, noting that clientele tends to be longer-staying couples. Accessibility has improved with direct flights to Key West International Airport from multiple major cities, making the Lower Keys a convenient retreat.
The Upper Keys, anchored by Key Largo, function as an extension of the Miami market. Proximity to Miami International and Fort Lauderdale-Hollywood International airports attracts buyers seeking quick escapes, but density and traffic are higher. This area suits those who want a weekend getaway rather than a permanent relocation.
Key West offers a vibrant mix with rich culture, nightlife, and walkability, but short-term rental licenses are limited and attached to properties, commanding premium prices. Tuttle advises buyers to consider their daily lifestyle, boating interests, rental income goals, and retirement plans to identify the right submarket. "It is not one size fits all," she said. Exploring the different communities across the Florida Keys is a useful first step, and connecting with a local expert makes the difference.
