Uncover the Island’s Haunted History on a Key West Ghost Tour

Beyond Key West’s breathtaking white sand beaches lies a world unknown to most- one of eerie tales and ghostly encounters. Embark on a Key West ghost tour and explore one of the country’s most haunted cities this Halloween season. From the terrifying legends of Robert the Doll at Fort East Martello to the Lady in Blue that still roams the halls of Captain Tony’s Saloon, endless ghost stories are waiting to be uncovered. Stay with Rent Key West Vacations and visit the island’s most haunted bars, restaurants, hotels, and cemeteries on one of these ghost tours:

Ghosts & Gravestones Tour

Sign up for a Ghosts & Gravestones Tour and explore the island’s haunted history with a Ghost Host. These eccentric hosts guide you through the evening on the Trolley of the Doomed, taking you through the historic Old Town to hear tales of murder, disease, and misfortune. Along the way, you will hear the story of Robert the Doll and pass haunted sites like Captain Tony’s Saloon. Then, you will disembark at the Key West Shipwreck Museum and learn about the cursed silver bar from a shipwreck!

Ghost Key West

Get up close and personal with the island’s most famous haunted resident, Robert the Doll, at Fort East Martello. Join Ghost Key West on the Fort East Martello Ghost Tour and learn about the haunted artifacts of the fort before sitting down for a lockdown with Robert the Doll. Want to do some ghost hunting during your visit? Sign up for the VIP ticket and gain access to ghost-hunting equipment and an additional hour at the fort. Explore the fort with your flashlight and try to capture evidence of the supernatural!

Key West Ghost Hunt

Key West Ghost Hunt is the island’s longest-running ghost tour, providing exclusive access to areas not visited by any other tour. Join local experts on a ghost tour around town with equipment like dowsing rods, K-II meters, spirit boards, and spirit boxes.

Key West Ghost & Mysteries Tour

Explore the haunted history of Old Town on foot with the Key West Ghost & Mysteries Tour. Get off the beaten path and walk past mansions, graveyards, and pubs while hearing first-hand ghost stories from your tour guide.

Reserve Your Key West Vacation Rental

Get off the beaten path and discover the city’s haunted history on a Key West ghost tour. Book one of our homes in the historic district and immerse yourself in the charm of Old Town. Every home has its own distinct architecture and history, from the grand Victorian mansions to the cozy conch cottages. Book with us today and experience the paranormal in the Florida Keys!

Experience Frights and Fantasy During the Key West Halloween Season

Rent Key West Vacations invites you to experience Halloween island-style in the southernmost city. Plan your visit during the Key’s spookiest season and experience the perfect blend of mild weather, seasonal events, and haunted attractions. The season’s highlight is the annual Fantasy Fest, bringing ten days of costumes, parades, and libations to our island paradise. Immerse yourself in the excitement of Fantasy Fest while enjoying everything the Key West Halloween season has to offer:

Fantasy Fest

Started in 1979 to increase fall tourism on the island, today Fantast Fest is Key West’s most popular event of the year. This ten-day festival welcomes as many as 75,000 visitors each year. Join the party and attend dozens of adult-oriented events, including costumed marches, street fairs, parades, and glamorous balls. Check out the 2024 schedule of events and experience the island’s biggest party this October.

Ghosts and Gravestones Tour

Uncover the island’s haunted history on a Ghost and Gravestones Tour this Halloween. Each tour is guided by a Ghost Host who will take you through the historic streets of Old Town aboard the Trolley of the Doomed. Pass the island’s most haunted sites and learn about tales of murder, lost tombs, strange dolls, and the Lady in Blue. Sign up for their Halloween Sights and Lights Tour for the ultimate outing!

Screaming Green Halloween

If you are looking for family-friendly fun, we recommend planning your visit around Screaming Green Halloween at Key West Tropical Forest & Botanical Garden. Learn fun ways to save the environment while enjoying kid-friendly activities like arts, crafts, games, and costume competitions.

Haunted Places in Key West

Key West is considered one of the most haunted cities in the country. Pay a visit to our most haunted places this Halloween season:

Audubon House and Gardens
Marrero’s Guest Mansion
Fort Zachary Taylor
East Martello Museum
Captain Tony’s Saloon

Plan an Unforgettable Key West Halloween Getaway

Pack your costumes and get ready for a frightful Key West Halloween getaway. Whether you are visiting for Fantasy Fest or want to soak up the sun on our beautiful beaches, we have an experience for everyone this fall. Visit the island with Rent Key West Vacations and find the perfect home away from home with our collection of over 140 vacation rentals.

7 Unique Things to Do in Key West

Beyond the famous Duval Street and Ernest Hemingway Home, Key West offers a wealth of unique experiences. Rent Key West Vacations invites you to venture off the beaten path and discover all the unique things to do in Key West. From haunted history tours to hidden gem restaurants and one-of-a-kind neighborhoods, our island has something to pique everyone’s curiosity. Head to Key West and discover the quirky island of the Florida Keys:

Stop at the Hellings Curry Museum for a free tour and explore one of the few brick structures on the island. Stroll through the building and learn about the history of this 19th-century mansion.
Pay a visit to Nancy Forester’s Secret Garden and visit the orphaned parrots at this educational sanctuary. Learn about Nancy’s mission to rescue, rehome, and train these parrots during your visit, and stop in for storytime from 10-11 daily.
Wander the streets of historic Old Town with Ghost & Gravestones and learn the haunted history of Key West. Follow your Ghost Host as you hear tales of murder, disease, and misfortune.
Stroll the unique and intriguing Key West Cemetery and use this map to learn about the island’s diverse heritage. Join the Historic Florida Keys Foundation walking tours twice a week.
Experience the Key’s Caribbean heritage at the historic Bahama Village Neighborhood. Stroll the streets and admire the Bahamian architecture, visit the Village Market for souvenirs, and stop for tapas at Santiago’s Bodega.
Learn all about Key West history at our newest museum: Sails to Rails Museum. Visit Key West Bight and stroll through exhibits featuring raw footage, unique artifacts, and a scale model of Fort Jefferson.
Discover the natural beauty of Key West on a Fury Cat Eco Tour. Board a catamaran and head to a backcountry sandbar for snorkeling, kayaking, watching wildlife, and relaxing.

Hidden Gem Restaurants in Key West

If you are looking for some delicious food off the beaten path, we have you covered. Stop at Garbo’s Grill at Hank’s Hair of the Dog Saloon for seasonal specialties like New England lobster rolls and poke bowls. And if you are looking for bars off the beaten path, we recommend going to Berlin’s behind A&B Lobster House. Settle into a cozy leather chair, order a drink from the speakeasy-style cocktail bar, and listen to jazz music as you sip on your cocktail.

Book Unique Lodging in Key West with RKW

Skip the hustle and bustle and check out all the unique things to do in Key West during your getaway with Rent Key West Vacations. Find unique lodging, like our 1840’s 11-bedroom Watson House Grand Estate, and stay in a piece of Key West history. Whether you want to stay in the historic district or near the beach, we have the perfect Key West vacation rental for your Florida getaway!

Where to Attend a Drag Show in Key West

As an internationally known LGBTQ+ travel destination, Key West Florida is celebrated for its inclusivity and openness. Among its many treasures, Key West boasts a dazzling drag show scene that is not to be missed. Attend a drag show in Key West and experience a night of comedy, glamour, costumes, entertainment, and laughter at Aquaplex, 801 Bourbon Bar, Mangoes, or La Te Da. Come as you are in and stay with Rent Key West Vacations, a proud Key West Business Guild member, a nonprofit organization promoting LGBTQ+ travel in the Keys!

Aquaplex Key West

Aquaplex offers drag shows every night in Key West! Attend a show at Aqua Bar and Night Club and witness the Aquanette’s showstopping drag performance. Aquaplex is also home to the island’s newest live act, The Birdcage Cabaret. See drag icon Christopher Peterson take the stage and show off impersonations while singing and lipsyncing with various local performers, female singers, and jugglers.

801 Bourbon Bar

Visit 801 Bourbon Bar and attend the longest-running drag show in Key West at 9 pm or 11 pm nightly. Meet the 801 Girls and expect a night of beauty and comedy with a variety of talented entertainers!

Mangoes

Mangoes hosts a special Sunday Drunken Drag Brunch once a month that is not to be missed. Plan your getaway around one of these fabulous brunches and experience Drag Queen performances, a live DJ, bottomless mimosas, specialty cocktails, and a la carte brunch food. Purchase tickets for upcoming events and proceeds will be donated to local charities.

La Te Da

Make your way to the La Te Da hotel and attend the Randy Roberts Live Cabaret show during your time in Key West. With over three decades of experience, Randy Roberts presents a classic drag show with live vocals, stunning costumes, and impersonations. Purchase tickets to the Tuesday, Friday, Saturday, or Sunday shows starting at 8 pm!

Welcoming Everyone to Our Key West Vacation Rentals

Check out the bustling nightlife scene during your visit and purchase tickets to one of the drag shows in Key West. Book your getaway with Rent Key West Vacations and find the perfect Key West vacation rental for your unique needs. For assistance customizing your Key West vacation, please contact us at 1-800-833-7368.

The Best Bars in Key West to Visit on Vacation

Key West is famous for its sunsets, turquoise waters, white sand beaches, rich history, and lively nightlife. Escape to the southernmost point in the U.S. with Rent Key West Vacations and check out the island’s top attractions during your visit. Make your way to Duvall Street and discover the best bars in Key West, offering refreshing cocktails, live music, happy hours, and local history. Whether you want to grab a drink at Ernest Hemingway’s favorite watering hole or catch the sunset at a bar along Mallory Square, there is a destination for everyone:

Sloppy Joe’s

Visiting the historic Sloppy Joe’s is a must during your Key West vacation. This bar has been a Key West tradition since 1933 and is famous for being Ernest Hemingway’s favorite watering hole. Hang out in a piece of Key West history and grab a drink at Joe’s Tap Room, serving craft beer and tasty cocktails. Joe’s also offers one of the best parties in town, with live music daily from noon to 2 a.m.

Green Parrot Bar

Another Key West icon, the building of the Green Parrot Bar, started as a grocery store in the 1890s, turned into a dive bar after WWII, and was renovated in the 1970s as the Green Parrot Bar. Today, the bar is a favorite destination for live music on the island, with live local musicians taking the stage multiple times daily.

Irish Kevin’s

Visit Irish Kevin’s on Duval Street for a classic Irish pub experience in the Keys. Enjoy unique cocktails like the world-famous Green Gator, featuring lemon rum, blue curacao, oj, sour mix, and 151 floaters in a souvenir glass. Stop in for live music, drinks, burgers, sandwiches, and delicious Key Lime pie!

Captain Tony’s Saloon

Captain Tony’s Saloon was the original location of Sloppy Joe’s Bar, located directly across the street. This historic saloon was the favorite watering hole for celebrities like Ernest Hemingway, Truman Capote, Tennessee Williams, and Jimmy Buffet. Unique pieces of Key West history are found all over the bar, including the stools painted with famous visitors’ names.

Sunset Pier

If you are looking for a Key West bar to watch the sunset over the water, we recommend visiting Sunset Pier near Mallory Square. Enjoy live music, tropical drinks, breathtaking sunset views, and delicious seafood.

Key West Vacation Rentals near Duval Street

Book your getaway with Rent Key West Vacations and stay close to the action with our vacation rentals in Old Town. Properties like Ann Street Cottage, Tranquility, and Namaste put you minutes away from the best bars in Key West. Stay within one block of Duval Street and two blocks from famous bars like Sloppy Joe’s, The Bull, and Hog’s Breath. To customize your vacation, please call our reservation specialists at 1-800-833-7368.