The Truman Annex Nightmare: Why Buying a Home in the Annex is a Bad Idea for Vacation Rentals

I am the first person to tell you to buy–and buy asap.

But, every now and then, there are exceptions. And this one is an exception that shouldn’t be kept behind closed doors.

Buying a home in the Truman Annex neighborhood is not for you if you want to list it as a vacation rental.

Were you aware that in 2025, the 280 transient rental licenses within the annex’s gates will expire, rendering it impossible to rent these homes on a transient basis?

Chances are, you may be asking why this should matter to you while looking to purchase a transient rental. Let me explain. A transient rental is where a Unit Owner (whether directly, indirectly, through an agent, exchange service or any other means) allows for the occupancy of his or her Unit by any party not occupying the Unit with the Owner of the Unit for a period of less than thirty (30) days. So, simply put, without a transient rental license, your property cannot be utilized as a short-term vacation rental. (If you need help figuring out or understanding the few exceptions to this rule, please reach out to me and let me offer you some clarity.)

Our team has also created a helpful ‘Key West Transient Property Finder’ map for your convenience. Visit it HERE. You can use ‘search’ to find licensed transient rental locations in the city of Key West and search for locations to determine if they are located in a transient receiver zone.

As a result of a lawsuit filed against various parties (Truman Annex Master Property Owners Association, the Shipyard Condominium Association and the City of Key West) almost 20 years ago, the city handed out these transient rental licenses. The settlement resulted in the 280 transient licenses being granted in Truman Annex with their sunset provision taking place in December of 2025, quickly approaching.

Our question is: Is the real estate agent you are working with in the Keys knowledgeable in vacation rental matters? If so, why did you not know about the sunset date approaching for these licenses?

Wanting more information on what this means for you as a potential buyer? Contact Rick Haskins, Brightwild Broker, today. (305) 916–9020