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 here in Key West. 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 will notify all 291 Truman Annex owners of the upcoming expiration starting next month.
“The city’s online licensing system is programmed to issue pro-rated renewal fees for the period
of Oct. 1 to Dec. 22, ensuring all Truman Annex transient licenses expire uniformly on
Dec. 22, 2025,” states a Sept. 3 memo from code enforcement director Christopher Counsellor to the mayor and commissioners.
Throughout November and December, “Property owners may apply for a non-transient license to rent on a long-term (or monthly) basis post-expiration,” Counsellor wrote. “The pro-rated fee for the new non-transient license (effective Jan. 1 to Sept. 30), will be $16.65. All active transient licenses for Truman Annex properties will be automatically closed in the city’s licensing system on Dec. 22, 2025.”
Anticipating the upcoming expiration, many local vacation rental companies have been alerting visitors to their website of the upcoming changes at Truman Annex, where properties will no longer be available for weekly rentals as of Dec. 22.
But that doesn’t mean there aren’t ongoing efforts by some property owners to persuade city officials to extend their more profitable transient rental rights.
Real estate broker and Truman Annex property owner Michael Behmke recently presented a proposal to other Truman Annex property owners. Under the proposal, the owners would ask the city to extend their short-term rental rights for another 20 years. In return, Truman Annex owners would spend $750,000 a year — totaling $15 million over 20 years — “exclusively on the acquisition of market-rate, multifamily residential units within the city of Key West.”
The properties purchased would be deeded to the city of Key West to be used exclusively and in perpetuity as affordable rental housing for Key West Police and Fire Department personnel.
“We believe responsible and well-regulated short-term rentals can be part of the solution,” Behmke told the Keys Weekly in an Aug. 27 email. “By leveraging rental opportunities, we can help generate resources and identify pathways to acquire or support properties specifically for attainable housing. This could offer a direct benefit to our first responders, while maintaining the character and integrity of our neighborhood. We are committed to continuing an open and constructive dialogue with residents, city officials, and community leaders. Our goal is to collaborate on a balanced approach — one that meets the needs of our community today while helping secure its future.”
Not all city officials, when reached by the Keys Weekly, were on board with granting special rental rights to a particular group of homeowners in a particular neighborhood.
“I had received requests for meetings about this from property owners back when I was running for office and in the start of my term, but lately, I haven’t heard a word from anyone seeking to extend the transient rental rights, probably because I started from the state that I would oppose it,” commissioner Monica Haskell said. “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.”
Mayor Dee Dee Henriquez and commissioner Donie Lee both echoed Haskell’s concerns about potential lawsuits from other property owners seeking transient rental rights. The mayor added that she has said since she first ran for office that she is not in favor of extending those special transient rental licenses.
“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. “The city made clear agreements with neighbors and residents years ago, and I believe those commitments must be honored. Any attempt to expand vacation rentals in this area would face strong community opposition, and I would insist that the issue be addressed only through an open and transparent public process.”
Commissioner Aaron Castillo, whose district includes part of Truman Annex, said on Aug. 26 that he wasn’t aware of any efforts to extend the transient rentals.
