Buying a Vacation Rental Property in the Florida Keys: What to Know About Regulations

If you’ve been dreaming of owning a piece of paradise in the Florida Keys, chances are you’ve also thought about renting it out as a vacation rental when you’re not using it. After all, what could be better than a home that not only pays for itself but also welcomes you back to the island lifestyle whenever you want?

Before you start counting rental income, it’s important to understand how vacation rentals work in the Keys. Regulations, location, and property features all play a huge role in whether your home will be a successful rental—or sit empty waiting for guests.

Not All Properties Make Good Vacation Rentals

One of the first questions buyers often ask me is: “How much can I make by renting this home out?”

Here’s the reality: not every property in the Keys is a strong vacation rental.

• Dry lot homes (those not on the water) are typically harder to rent. Visitors come to the Keys for fishing, boating, and waterfront views, so they naturally gravitate toward properties with water access.

• Homes directly on the open water or on a canal with quick access to the ocean or bay are in much higher demand.

• A swimming pool is another must-have for most renters. After a day on the water, vacationers love having a pool to relax by.

Understanding Rental Regulations

Vacation rental rules vary by community, so it’s essential to know what applies to the property you’re considering.

• Most single-family neighborhoods in the Keys have a 28-day minimum rental period. This means you can’t simply rent your home out by the week (with one big exception below).

• Marathon is the exception to the rule. The City of Marathon has a much more relaxed approach, allowing shorter-term rentals. That’s why Marathon is such a hotspot for investors looking to maximize vacation rental income.

• Neighborhood and HOA rules may also restrict rentals. Some subdivisions don’t allow them at all, while others may have specific requirements.

What This Means for Buyers

If your goal is to generate rental income, focus on homes that:

✅ Are on the water (open water or quick canal access)
✅ Include a pool
✅ Fall within an area or municipality that allows short-term rentals (like Marathon)
✅ Don’t have restrictive HOA rules against vacation rentals

The good news is, once you find the right property, demand is strong! The Florida Keys remain one of the most desirable vacation destinations in the U.S., and renters are willing to pay top dollar for the right home.

Final Thoughts

Buying a home in the Keys can be both a lifestyle choice and an investment. The key (no pun intended!) is knowing the local rules and choosing a property that truly appeals to vacationers. With the right property and the right location, you can enjoy your own slice of paradise—and let it work for you when you’re not here.