Most Haunted Places in Key West

Posted by in US Ghost Adventures

For many, Key West is the perfect vacation destination. Located at the southernmost point of the Florida Keys, it has no shortage of sunshine, sandy beaches, and delicious seafood. There’s a rich literary history in Key West thanks to figures like Ernest Hemingway and Tennessee Williams. Key West’s sunsets are famous, and every evening is a celebration when the sun slips beneath the waves. 


Key West is just as popular with ghosts as tourists. 


Spooky Facts About Key West, FL:

  • Key West is nicknamed “The Island of Bones”. 
  • The Key West Cemetery is said to be haunted by many people who died tragic deaths wandering the grounds. There’s even a legend of The Bahamian Guardian who watches the cemetery, chasing away anyone who disrespects the dead.
  • One of the most famous spooky attractions in Key West isn’t a place—it’s a doll. Robert the Doll is said to be cursed, bringing bad luck to anyone who doesn’t treat him with respect. 


There’s plenty of otherworldly excitement waiting for you in Key West. Keep reading to discover the most haunted hotspots in Key West. See them in person on a ghost tour with Southernmost Ghosts!

The Firehouse Museum

Nestled within a historic fire station, Key West’s Firehouse Museum offers a glimpse into the unique firefighting past of the Florida Keys. Built in 1907, it originally housed both the Sunnysouth Engine Company and Tiger Hose Company No. 3 and even braved the wrath of a 1909 hurricane that ripped through the island. 


After serving the community for nearly a century, Station No. 3 finally closed its doors as a functioning firehouse in 1998. Thanks to the tireless efforts of local historian Alex Vega and the Old Firehouse Preservation Inc., the station was reborn as a museum in 2010. 


Who Haunts the Oldest Firehouse in Florida?


There is a young girl who wanders the halls with ethereal ease. No one knows who this mysterious girl is, but many believe that she is Elena Hoyos, a 22-year-old who died from tuberculosis in Key West. Hoyos lived a short life and strange death, as her body was exhumed by Carl Von Cosel, a German radiologist living in Key West, and kept in his home for seven years. 


Another intriguing story surrounds the missing fire chief, Joseph “Bum” Farto. The notorious chief was involved in the drug trade and caught dealing cocaine in 1975. He was sentenced and then promptly disappeared. Bum’s whereabouts remain unknown, but some believe his spirit hangs out at the museum. 


More Hauntings at The Firehouse Museum


  • A full-bodied ghost named Frank has been spotted in the men’s restroom at the museum. He looks so convincingly alive that others have mistaken him for a human guest. 
  • A young African American girl dressed in early 20th-century clothing appears in pictures of the firehouse. 

Old Monroe County Jail

The Old Monroe County Jail’s story begins in 1892 when it was constructed to replace inadequate jails on the site. With Key West’s booming population, the jail grew over the years before closing its doors in 1965. The harsh realities of the jail’s past – cramped cells, brutal conditions, and desperation – are believed to have left a permanent mark on the building’s energy.

Visitors often report unsettling experiences, including disembodied voices and footsteps echoing through the halls, particularly in the isolated confinement cells. Objects have been known to move inexplicably, and some have described a bone-chilling sense of being watched, a constant reminder of the countless souls who passed through the jail’s unforgiving walls.


Why is the Old Monroe County Jail Haunted? 


One story centers around the spirit of Manuel Isleño Cabeza. In 1921, Cabeza was lynched by a mob outside the jail after the Ku Klux Klan discovered his relationship with a mixed-race woman. He survived the initial attack but was killed later when mob members broke into the prison, hanged him from a palm tree, and shot him. Cabeza’s presence is said to linger near the former gallows, manifesting as anger and despair. Visitors have reported shadowy figures resembling Cabeza, and their encounters have left them shaken.  


There’s another legend that says Angel, the mixed-race woman that Cabeza was involved with, put a curse on the white supremacists who murdered her lover using Voodoo magic. Every single one of the men engaged in Cabeza’s death met an untimely end. One drowned at sea; another was blown up; one mysteriously disappeared, and another was killed in a boating accident. The police officer who let the men into the jail was also killed in a fishing accident. Perhaps it was all coincidental – or maybe they all succumbed to Carribean witchcraft. 

House of Captain Watlington (AKA the Oldest House)

The House of Captain Watlington, known as the Oldest House Museum, was built in 1829 by a skilled ship carpenter named Richard Cussans. Captain Francis Watlington, a prominent figure in Key West, acquired the house and expanded it to accommodate his wife Emeline and their nine daughters. The Oldest House became a social center of sorts, a place where the Watlingtons hosted gatherings and embraced the growing community spirit of Key West.


Who Haunts the Oldest House in Key West? 


The Oldest House in Key West, also known as the House of Captain Watlington, is rumored to be haunted by its former residents. The most prominent spirit is believed to be Captain Watlington himself. Visitors have reported feelings of being watched and disembodied footsteps, particularly in areas that the Captain frequented during his life.

The Porter Mansion

Constructed in 1838, it began as a two-story residence believed to have been built by Judge James Webb. It wasn’t until Dr. Joseph Yates Porter purchased the property in 1845 that it became forever associated with the Porter name. Dr. Porter was a prominent figure who served as Florida’s first Public Health Officer. One of his most notable contributions was understanding how mosquitoes transmit yellow fever.

Dr. Porter resided in the mansion for his entire life, dying in the same room where he was born. Over the years, the mansion underwent renovations, transforming from a simple structure to a three-story architectural marvel that incorporated Bahamian, New England, and French influences. 


Who Haunts The Porter Mansion in Key West? 


The Porter Mansion in Key West is rumored to be haunted by its most famous resident, Dr. Joseph Yates Porter himself. Sightings of a full-bodied apparition resembling Dr. Porter have been reported, while others have experienced disembodied voices and strange occurrences. Residents and occupants have shared stories of objects being moved inexplicably, coins appearing out of nowhere, and even the faint strains of classical music. He has also been known to throw wine glasses across the first-floor bar.

Marrero’s Guest Mansion

Originally a stately Victorian home built in 1890-1891 by Francisco Marrero, a prominent local cigar maker, the mansion has transformed into a captivating boutique hotel.  Meticulously restored, the architecture retains its historic character, featuring intricate details and original millwork.  


It’s a great place to stay if you’re interested in the unearthly. Legend has it that Francisco Marrero built the home for his second wife, Enriqueta, and their children. Sadly, Marrero then died, and his first wife promptly evicted Enriqueta and her family from the home. Enriqueta left but vowed to always remain at the home in spirit. 


Nowadays, visitors swear they can see and feel Enriqueta’s presence at the stunning resort. A few rooms are associated with her, the most prominent being Room 18. Enriqueta will also sway the chandelier in the lobby if a guest checks in with a poor attitude.

Captain Tony’s Saloon

Steeped in history and fueled by legend, Captain Tony’s Saloon in Key West, Florida, is more than just a watering hole. The building dates back to 1851, serving various purposes throughout the years that offer a glimpse into Key West’s wild past. The transformation into a saloon came in the early 20th century, and it wasn’t long before Captain Tony, a colorful character who embodied Key West’s adventurous spirit, took the helm. Tony, a suspected rumrunner and one-time mayor, became synonymous with the bar and successfully created a welcoming atmosphere that attracted a motley crew of locals and visitors.


Captain Tony’s Saloon quickly became a magnet for creative energy. Ernest Hemingway was a regular, and Jimmy Buffett found a home for his growing music career on the saloon’s stage. Poet Shel Silverstein likely penned some of his verses while perched on a barstool. These famous faces and countless others helped solidify Captain Tony’s Saloon as a legendary Key West hangout.


Who is Buried at Captain Tony’s in Key West? 


You’ve been to haunted bars, but have you ever been to one with a gravestone embedded in its floor? Elvira was a former bar patron with a penchant for gambling and lively company. She spent a lot of time at the bar, which could explain why the folks at Captain Tony’s felt the need to bury her there. 


Elvira’s gravestone is embedded in the saloon’s floor, a constant reminder of her presence. Guests and staff have reported feelings of being watched or chills near the gravestone, and some even claim to have seen her ghostly apparition flitting about the bar.

More Hauntings at Captain Tony’s

  • The Lady in Blue was sentenced to death by hanging on the tree next to Captain Tony’s bar. She was found guilty of murdering her family and now is believed to haunt the bar that’s located so close to her final resting place.
  • Captain Tony’s Saloon has a ghost cat named Clementine. A beloved feline who once frequented the saloon, Clementine still likes to keep an eye on the place. Patrons have seen glasses move on their own and felt a phantom feline brush against their leg. 
  • A young woman is believed to reside forever near the bar bathroom. An old legend says that the woman once came to the bar in search of her husband. When she found him flirting with another woman at the bar, she left her baby in the bathroom. While it’s unknown what happened to the woman, visitors feel a strange energy in the women’s bathroom, and some have reported seeing the bathroom door open on its own. 

Hemingway House

Built in 1851, the Spanish Colonial-style house was originally a two-story residence. In 1931, renowned author Ernest Hemingway and his wife Pauline purchased the property. The Hemingways significantly renovated the house, transforming it into their Key West haven for the next eight years. During this time, Hemingway penned some of his most acclaimed works, including “For Whom the Bell Tolls” and “Death in the Afternoon.”


Why Does Hemingway Haunt the House? 


Unfortunately, Hemingway died by suicide in 1961. But if you visit the Hemingway House, you might believe he’s alive and well. Visitors have reported sightings of a shadowy figure resembling Hemingway, particularly on the second-floor balcony where he was known to write. Others have described a feeling of being watched or his presence in his former workspace.


Two neighbors described a particularly disorienting experience when passing the Hemingway House in the early 1960s. They waved at what they believed to be Hemingway sitting at his typewriter near a window. They later learned of Hemingway’s death and couldn’t believe what they had witnessed. 

East Martello Fort and Museum

The history of the East Martello Fort and Museum blends military might with cultural preservation. Construction of the fort began in 1862 during the Civil War when it was intended to defend the island from potential Confederate attacks. However, the Union victory in the Civil War rendered the fort largely obsolete before it was finally completed.


In 1950, the Key West Art & Historical Society transformed it into the island’s first museum.  Today, the fort is a popular tourist destination, showcasing Key West’s vibrant history through engaging exhibits. Some, however, are more intriguing than others.


Robert the Doll 


Among the many intriguing exhibits at the East Martello Fort and Museum, Robert the Doll stands out as a local legend. According to lore, Robert belonged to a young boy named Eugene Otto in the early 1900s. Strange occurrences plagued the household whenever Robert was separated from Eugene, leading some to believe the doll was cursed.


Today, Robert resides in a glass display case at the museum. Legends claim that failing to show respect to Robert, like neglecting to ask permission before taking a photo, can result in misfortune. Museum staff anecdotally report strange occurrences around Robert, and some visitors have shared their experiences of feeling uneasy or ill after encountering the doll. 


The Curse of Robert the Doll

  • There are many stories about the misfortunes that strike those who disrespect Robert. Some stories mention car accidents, broken bones, job loss, or relationship troubles striking those who take his picture without permission or treat him with disdain.  
  • Some people have captured EVP recordings near Robert’s case. These EVPs can be interpreted as whispers or disembodied voices.
  • Museum staff swears that they have seen Robert’s facial expression change. Items near Robert’s case sometimes move on their own, as well.

Haunted Key West

Key West will thrill you with its beautiful beaches, great dining and nightlife, and endless opportunities for ghost hunting. From old hotels to museums and more, there are many haunted places in Key West, and they’re all waiting for you to explore them! 


If you want to explore the most haunted places in Key West, book a Key West ghost tour with Southernmost Ghosts. Check out our blog for more macabre tales of America’s most haunted!