Most buyers start their Florida Keys home search online, but according to Sandy Tuttle, founder and owner of Island Welcome Real Estate, a boutique firm based in the Lower Florida Keys with 22 years in the market, the first question should be about which part of the Keys they are actually looking for. The four main submarkets—the Lower Keys, Marathon, the Upper Keys, and Key West—are genuinely different places with different 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 with no 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, which suits some buyers but pushes others elsewhere.
The Lower Keys, running from just south of the Seven Mile Bridge to Key West, still feels like the old Keys. Monroe County requires a 30-day minimum rental term for 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. Accessibility has improved with direct flights to Key West International Airport from cities like Dallas, Charlotte, and New York. From anywhere in the Lower Keys, the airport is no more than 40 to 45 minutes away.
The Upper Keys, anchored by Key Largo, is an extension of the Miami market, capturing day-trippers and weekend visitors. Proximity to Miami International Airport and Fort Lauderdale-Hollywood International is a draw for those still working in South Florida, but the trade-off is higher density and traffic. The buyer profile tends to skew toward those seeking a quick getaway rather than permanent relocation.
Key West offers a mix of opportunities with rich culture and nightlife, but short-term rental licenses are limited and rarely available, commanding premium prices when sold. Tuttle runs through consistent questions with buyers: daily life goals, boating interests, rental income needs, 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, then connecting with a local expert makes the difference.
