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Key West Historic Inns
Key West has always belonged to those who see life a little differently. Across five historic inns in Old Town, Key West Historic Inns captures that same independent spirit, each offering its own way to experience the island. Walk to Duval Street, wander toward the water, spend the afternoon by the pool, or follow the day wherever it leads. Choose your adventure, choose your inn, and discover a Key West that goes well beyond the postcard.
Five boutique hotels.
Five distinct personalities.
One unforgettable Key West.
Eat & Drink
Good food has a way of bringing people together. Across the Key West Historic Inns collection, every stay is just a short stroll from Isabel’s and The Bungalow Bar, where poolside lunches, tropical cocktails, and easy afternoons are always on the menu.
Gather & Celebrate
Some trips are better shared. From milestone birthdays and family reunions to wedding weekends, celebrations, and long-overdue getaways with friends, Key West Historic Inns gives your group a place to make the island your own. Choose from five distinct Old Town inns, each with its own personality, gathering spaces, and easy access to Duval Street and the best of Key West.
Exclusive Offers
First Timers Guide to Key West
There’s more to Key West than Duval Street. Get to know the island through the places, flavors, stories, and traditions that give it its character, with a few of our favorite ways to experience Key West like you’ve been coming here for years.
See What's Happening
Rum, Lime, and Sunshine
Buy One, Get One Margaritas & Mojitos
🌴 Bungalow Bar at Winslow’s Bungalows
🌴 Isabel’s at Lighthouse Hotel- 2:00 PM to 4:00 PM
Paradise, Poured
Cypress Sangria
Mallory Square Sunset
A nightly Key West tradition of sunsets and waterfront entertainment.
🌴 Mallory Square
- 4:00 PM to 7:00 PM
Happy Hour
A daily Key West tradition.
🌴 Bungalow Bar at Winslow's Bungalows
🌴 Isabel's at Lighthouse Hotel- 4:00 PM to 6:00 PM
Greatest Hits Pool Party
Greatest Hits Pool Party takes center stage during Fantasy Fest.
🌴 Winslow's Bungalows
- 12:00 PM to 4:00 PM
Sam Carlson
Wine Down Wednesday
Throwback Thursday
Farmer’s Market
Shop local produce, artisan foods, and handmade goods.
🌴Truman Waterfront Park
- 1:00 PM to 6:00 PM
Jamie Sellers
Sam Carlson
Flocktail Friday
Aaron Luka
Wavy Davy
Toko Irie
Nina Newton
Gi & Rolando
Trop Rock’N Duval
Trop Rock’N Duval
Trop Rock’N Duval
Live music and poolside fun with Reggie Starrett.
🌴 Winslow's Bungalows
- 2:00 PM to 5:00 PM
Wichita Jack
Nina Newton
Trop Rock’N Duval
Live music and poolside fun with Dave Freeman & Friends.
🌴 Lighthouse Hotel
- 4:00 PM to 7:00 PM
Drag Me To Lighthouse
World’s Fastest Boat Parade
The excitement of offshore racing brought to the heart of Old Town.
🌴 Duval Street
- 4:00 PM to 5:00 PM
Race World Offshore World Championship
Bringing the world's fastest offshore powerboats to the Key West waters,
🌴 Various Locations in Key West
- All Day
Lighting of the Bight
Watch the Historic Seaport come alive with twinkling lights and nautical Christmas displays.
🌴 Historic Seaport
- All Day
Holiday Parade
Christmas takes to the streets as the annual Key West Holiday Parade.
🌴 Duval Street
- All Day
Holiday Boat Parade
Beautifully decorated boats illuminate the Historic Seaport.
🌴 Historic Seaport
- 6:00 PM to 12:00 AM
New Year’s Eve Events
Ring in 2027 with Key West's legendary New Year's Eve drops.
🌴Various Locations in Key West
- All Day
Literary Seminar
Celebrate Key West’s literary legacy with acclaimed authors.
🌴Various Locations in Key West.
- All Day
Half Marathon & Runfest
Four races and a full weekend of island celebrations.
🌴Various Locations in Key West
- All Day
Mile 0 Fest
Five days of Red Dirt, Americana, sunshine, and island energy.
🌴Various Locations in Key West
- All Day
Food & Wine Festival
Five continents, incredible wines, and celebrated chefs.
🌴 Various Locations in Key West
- All Day
Seafood Festival
Conch Republic Independence Celebration
