Property Management Blog

Go The Distance Caballero Pushes Long-Term Rentals

System - Wednesday, December 14, 2016

By Terry Shmida

Key West real estate broker and property manager Jaime Caballero has a message for her colleagues: Please educate clients on the benefits of renting their properties for the long term, rather than as vacation rentals.

Caballero, who was born and raised in the Southernmost City, is the president-elect of the Florida chapter of the National Association of Residential Property Managers, and a board member of the Key West Association of Realtors.

It is in her capacity as a licensed real estate broker with Key West Residential Property Management that Caballero, who has been involved in property management since 1989, is hoping to convince other property managers, real estate agents, and investment property purchasers themselves to consider the benefits of longer term rentals to themselves – and the town in general.

“First of all, let me be clear, I’m not trying to reach those people who own or manage properties with transient rental licenses,” she said. “Nobody should ever give up a nightly rental to long term rental. What I’m concerned about is the growing number of non transient short-term rentals. There’s a shortage of housing here. And what’s been happening a lot lately is that homebuyers, sometimes on the advice of the agent that sold them their property, are renting it out by the month as a vacation rental, for a few months of the year, during season, rather than seeking annual long-term tenants. That practice may bring in higher monthly income for those three or so months, but leaves the owner in the position of taking their chances on finding more short-term tenants during the slower months, or only being able to offer a potential long-term tenant a nine month rental.”

The former problem, that of finding short-term tenants outside of tourist season, is a problem for the homeowner. The latter issue, that of the lack of full-year rentals, is undermining her hometown, Caballero said.

“I’ve spoken to people in the military and the service industry who are moving here and can’t find a landlord willing to rent them a home or apartment year-round,” Caballero said. “That leaves them unable to find somewhere to live because they don’t want to have to move after nine months. These people are our city’s workforce. Ultimately it’s not good for any of us to be in this situation.”

Besides the peace of mind and more money that lower but steadier long-term rent collection can bring to residential property owners, there is another benefit, according to Caballero: Lower commissions payable to property managers such as herself, since long term commissions are lower than vacation rental commissions. “You don’t have an expense of utilities while the property isn’t being rented,” she said. “Obviously, paying fewer expenses and making more income is a better way for property owners to go.”

Caballero worked for the Spottswood Family Trust for 14 years, in accounting and property management. In 2003, she obtained her real estate license and went to work for Century 21 Prestige Realty Group for the next six years. Her portfolio consisted of 100 or so properties that were a mixture of long term rentals and vacation rentals.

In 2009, Caballero became a real estate broker and founded Key West Vacation Properties & Realty. Later that same year she opened Key West Housekeeping Services to better serve her clients.

In 2012 she opened Key West Residential Property Management in order to expand her long term property rental pool.

She can be reached at 305-296-6667, 305-797-5252, or at and

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