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Posted on: December 14, 2019

Tavernier woman accused of vacation-rental tax theft

This is Dessirree Bennett

PLANTATION KEY, December 14, 2019 – A Tavernier woman accused of failing to remit taxes on a condominium she rents out has been charged with felony theft.

Dessiree Bennett, 54, was arrested on a warrant a little before midnight December 11, charged with theft of sales tax more than $300, less than $20,000; and a misdemeanor count of failing to obtain a certificate of registration. State Attorney’s Office Investigator Chris Weber investigated the case with the Monroe County Tax Collector’s Office and prepared the arrest affidavit.

Monroe County requires owners of rentals of six months or less to open a tourist development tax account with the Tax Collector’s Office. Owners of such rentals must remit a 5 percent tax on those rentals to the Tax Collector’s Office.

Bennett owns a condo in the Moon Bay complex at mile marker 104.3 in Key Largo. The Tax Collector’s Office received a tip it was being illegally rented out so an employee checked and saw it advertised for short-term rental on the Airbnb and Vrbo websites. The condo does not have a rental tax account associated with it.

When the Tax Collector’s Office informed Bennett of the tax responsibilities for a rental, she provided the office with documentation showing Aibnb paid her $34,820.09 for rentals at the condo in 2018 and 2019. However, Bennett still didn’t register the condo and never paid the $1,177.72 in taxes owed based on the amount Airbnb paid.

Bennett still owes the tax liability, plus penalties and interest and possibly more in past taxes.

In 2015, the Monroe County Commission requested the Tax Collector’s Office to make auditing and enforcing such taxes a priority and allowed the office to search rental websites to find illegal rentals in an effort to bring them into compliance

“Everyone has to be compliant,” Tax Collector Danise Henriquez said. “It doesn’t matter the amount, whether it is a homeowner or hotel. Everyone needs to be compliant.”

“This is something that has been demanded not only by the commission but the taxpayers of Monroe County,” said Pam Sellers, the office’s senior tourist development tax auditor. “There are people who pay their taxes.”

Tips about possible illegal rentals can be sent to or called into 1-855-422-4540.

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