“They’ve had a good deal for 20 years and now it’s over. I’ve stuck with that since before I was elected.”
That was Key West Mayor Dee Dee Henriquez, speaking on Dec. 16 about the ending next week of short-term rentals inside the gated Truman Annex neighborhood.
As of Monday, Dec. 22, property owners in Truman Annex are no longer allowed to rent their properties for any period shorter than a month. The deadline is the result of a legal settlement that was agreed upon back in 2005.
Twenty years felt like some far-off date in the future back in 2005. It was the year of Hurricane Katrina in New Orleans and Hurricane Wilma in the Keys. An online video platform called YouTube had just launched and the world was picking sides in the “Brangelina” relationship.
In Key West, 2005 also brought an end to years of lawsuits and appeals, with a settlement agreement granting property owners in the Truman Annex neighborhood 20 years of transient rental rights.
Owners could offer their units for weekly rentals, which are significantly more lucrative than the monthly vacation rentals allowed at most properties in town without a pricey transient rental license.
That special transient rental license, granted only to the 300 or so Truman Annex property owners, and only for 20 years, expires Dec. 22.
City officials sent a letter on Dec. 5 notifying all Truman Annex owners of the upcoming expiration.
“In accordance with the 2005 Truman Annex Settlement Agreement, all transient licenses associated with the affected properties will be placed into inactive status and void on Dec. 22, 2025,” the letter states. “As of that date, the property will no longer be authorized to advertise or operate as a short-term rental.
“Additionally, the city-issued medallion currently affixed to your property must be returned to the City of Key West Licensing Division no later than Feb. 1, 2026.”
Property owners and property managers may apply for a non-transient license to rent on a long-term (or monthly) basis from now on. Non-transient licenses cost $16.65.
“All active transient licenses for Truman Annex properties will be automatically closed in the city’s licensing system on Dec. 22, 2025,” states a September letter from the city, meaning those transient licenses will not be circulated and available for purchase by property owners in other parts of town.
Anticipating the expiration, many local vacation rental companies have been alerting visitors to their website of the upcoming changes at Truman Annex.
But that doesn’t mean there haven’t been ongoing efforts by some property owners to persuade city officials to extend their more profitable transient rental rights. Recent discussions have raised the possibility of the Truman Annex owners hiring an attorney to try to reclaim short-term rental rights.
As of September, city officials reached by the Keys Weekly were not on board with granting special rental rights to a group of homeowners in a particular neighborhood.
“I stated from the start of my term that I would oppose it,” commissioner Monica Haskell told the Keys Weekly in September. “Any investor down there had adequate notice of the date these rentals would end. People can still rent their units out for a month at a time, as they can nearly anywhere in the city. But if we gave Truman Annex new transient licenses, we’d likely be subject to multiple lawsuits from every other property owner who wants permission to offer transient rentals. The city has made a lot of mistakes with Truman Annex in the past, such as when it tried and failed to develop the property into housing but was unable, and ended up selling it to a private developer. But there’s no reason we need to continue to perpetuate those mistakes.”
Henriquez and commissioner Donie Lee echoed Haskell’s concerns about potential lawsuits from other property owners seeking transient rental rights. “When I first got into office, I met with the folks who were interested in extending the rentals and were offering the city money or housing for workforce housing,” Lee said. “But the reason I don’t support that is because I was advised by our former city attorney that if we did that for Truman Annex, then we’d have to offer transient rental rights to everyone who wants them and that would be a Pandora’s box that I’m not willing to open.”
“I am not aware of any proposal to extend transient vacation rentals in the Truman Annex, and I would not support such an expansion,’ commissioner Sam Kaufman said in September. “The city made clear agreements with neighbors and residents years ago, and I believe those commitments must be honored.”
