The History of the Key West Jail

The Old Key West Jail

The 1892 jail had been specifically designed to mimic the Monroe County Courthouse, built just two years earlier. Both the Key West Jail and Monroe Courthouse were symbols of Monroe County’s position as the most populous city in Florida at that time with the U.S. Census showing more than 18,000 citizens in Key West.

The 1892 jail was the fifth jail built at the historic Jackson Square. In 1907, a 10-foot-high concrete wall was built around the jail and in 1910 the jail was expanded to increase capacity with a two-story concrete cell block.

In 1952, the front of the old jail was demolished and replaced with a new jail and office for the Monroe County Sheriff. In 1965, the sheriff’s office was replaced with a courthouse annex. This annex was expanded in the 1980s. At that time, the north section of the 1907 wall was removed. Today, only the rear portion of the 1892 building remains, along with the entire 1910 addition and the 1910 cell block.


Monroe County Project Management will start the restoration of the 1892 Key West Jail in early 2020. The first phase includes roof replacement, door and window restoration, and spalling repairs. In the second phase, non-historic features of the building will be removed and fire protection, required ADA access, restrooms, and museum facilities will be added. The tentative opening date is summer 2021.

A small section of the original 1892 building and the entire 1910 addition remain. The goal of the project is to save the original structure and remodel a portion of the building to operate as a museum.

“This project will be a celebration of law enforcement and the Florida Keys’ unique history with the early jail system,” said Cary Knight, Director of Project Management. “There has been a considerable amount of research to make it a historical experience for our residents and visitors to Key West.”

Earlier this year the Key West Art and Historical Society (KWAHS) submitted a proposal to operate and maintain the museum that was accepted by the Board of County Commissioners. The KWAHS also manages the County-owned Fort East Martello and the Key West Lighthouse.

“This has been a long effort to preserve this special piece of Monroe County history,” said Michael Gieda, Executive Director of KWAHS. “This partnership with the County has been a win-win for historic preservation and education.”

Monroe County commissioned a full historical structure report with a Historic Preservation Grant in 2018. The project will be funded through a Tourist Development Council’s bricks and mortar grant and a Florida Division of Historic Resources special category grant.

How to Bond out of the Key West Jail.

Key West Bail Bonds

The Town

            The Florida Keys in Monroe County, Florida attracts up to five million visitors a year from all over the world. A good portion of these tourists end up in Key West which is known for its care free, island lifestyle, and the world-famous downtown party zone “Duval Street”. Duval Street is just over a mile long, runs north to south, and houses the largest collection of eateries, saloons, and niche stores in town. A small portion of those visitors may end up needing the services of a Key West Bail Bondsman.

Although Key West, Florida is well known as a party town that does not mean it is free of laws or law enforcement. The Key West Police Department, the Monroe County Sheriff’s Office, and The Florida Fish and Wildlife Conservation are just a few of the active law enforcement agencies in town. Locally, law enforcement is supported and proactive in nature. Unfortunately, sometimes people make mistakes and situations occur where some is placed under arrest.

After Arrest

When someone is arrested within Key West, they will be transported to the Monroe County Jail Key West Facility for processing. The Monroe County Key West Jail is located at 5501 College Road, Key West, Florida, 33040.

Once the arrestee arrives at the Monroe County Key West Jail, it will usually take several hours for the arrestee’s charges and bond amount to become available. This delay is because that information is not accessible until after the arresting Key West Police Officer or Monroe County Sheriff’s Deputy finishes writing the arrest affidavit. The arrest affidavit contains the narrative of the probable cause for arrest and list of charges.

There are several different kinds of arrests with a few being a bench warrant, a capias, a probable cause arrest, and a writ.

If an arrestee is in custody on a warrant arrest which includes Violation of Probation, Failure to Appear, Violation of Pre-trial Services, etc. their bond will already be set and they will be able to bond out at that time unless it was set as  No Bond Allowed by a Key West judge.

If the inmate of the Key West Jail is being charged with any Probable Cause Felony arrest and most misdemeanors, they will not have a bond right away. They will first have to attend a first appearance hearing with a Monroe County, Key West Judge. There is a first appearance hearing scheduled every day of the week and all year round. There is only one first appearance hearing each day. If you are arrested too late in the day, and miss that days hearing you will be required to spend the night inside of the Key West Jail and attend first appearance the next day.

During the hearing the Key West Judge will review the arrest affidavit and decide if there is probable cause for the arrest. If the Key West Judge decides there is probable cause for the arrest, he will then decide to set cash or surety bond (secured) for each charge or grant the arrestee Pre-trial release (release without secured bond). The arrestee will then be provided an arraignment date to return to court at a later date.

If the judge decides there is not sufficient probable cause for the arrest, they may in essence drop the charge on the spot.

If the arrestee was given Pre-Trial Release, they will be released from the Key West Jail, usually within a few hours.

Bonding Out

            If the Key West Judge gave the arrestee a $5,000 Bond (just for example). You then have two options, Cash, or Surety.

Cash – You will go directly to the Jail with $5,000 in cash and secure the arrestee release. If you do not wish to post cash at the Jail you can call (305)451-2593.

We will provide you with a Key West Jail Surety bail bond. A Bail Bond can only be provided by a licensed Florida Bail Bondsman. A licensed Florida Bail Bonds will charge you a 10% of the total amount of the bond, with a minimum of $100 per charge plus security for the total amount of the bond. The security may be as simple as a co-signer signature depending on the specific situation.

            We will then secure the release of the inmate by providing the total bond to the Key West Jail. The arrestee will then be released from the Key West Jail within hours. After being released from the Key West Jail, the arrestee must attend all court hearings, or have an attorney appear, until the case is completed.