Key West Historic Inns

The Studios of Key West is a historic Old Town arts center offering sunset rooftop happy hours, rotating art exhibitions, performances, film screenings, workshops, and unique spaces for meetings and events bringing together local and visitors in an inspired island setting.

Enjoy Tito's drink specials all day at The Bungalow Bar, located at Winslow's Bungalows. From your first afternoon cocktail to an evening nightcap, discover refreshing Tito's favorites served throughout the day in the heart of Old Town.

Join us each afternoon at Ella's Cottages for a complimentary glass of Roseblood Rosé, offered daily from 3:00 PM to 4:00 PM.

Gather at Ridley House each afternoon for a complimentary glass of our signature Cypress Sangria, thoughtfully crafted in-house and served daily from 3:00 PM to 4:00 PM.

Sip, relax and unwind with drink specials served daily at Isabel's at The Lighthouse Hotel.

Join us for an extended daily local favorite with half off select libations from 4 – 6 PM.

Sip, relax and unwind with drink specials served daily at Bungalow Bar at Winslow’s Bungalows.

Join us for an extended daily local favorite with half off select libations from 4 – 6 PM.

A nightly festival and community tradition held right on the waterfront at Mallory Square. Every evening, locals and visitors gather to watch the sun sink into the Gulf of America while soaking up a lively arts-festival atmosphere.

Ease into the island’s rhythm with live music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

Midweek is the perfect time to slow the pace and enjoy a glass of wine in the heart of Old Town. Every Wednesday from 6:00 PM until close, join us at The Bungalow Bar for half off wines.

Raise a glass to the classics every Thursday at The Bungalow Bar. Enjoy $10 classic cocktails all day, featuring timeless favorites served in the relaxed setting of Winslow's Bungalows.

Key West Farmers Market brings local vendors together every Thursday from 1–6 PM at Truman Waterfront Park, featuring fresh produce, artisan foods, native plants, handmade goods, and local crafts. A perfect way to shop by the sea and experience the island community.

Ease into the island’s rhythm with live music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

Ease into the island’s rhythm with live music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

Think pink and join us for Flocktail Fridays at Isabel's Lighthouse. Wear your favorite pink attire, tag @KeyWestHistoricInns in your social post, and receive 10% off your bar tab from open to close.

Spend the afternoon with live music from Wavy Davy at The Bungalow Bar at Winslow's Bungalows. Find a spot by the pool, enjoy a refreshing drink, and let the laid-back sounds of the island carry you through the day.

Kick off your Friday with live music from Aaron Luka at Isabel's Lighthouse. Blending acoustic favorites with an easygoing island style, Aaron's performances set the tone for a relaxed afternoon in the heart of Old Town.

Start your Saturday with the sounds of reggae as Toko Irie performs live at The Bungalow Bar. Known for his smooth rhythms and uplifting island sound, Toko Irie brings an authentic reggae performance to the heart of Old Town, creating the perfect backdrop for a leisurely morning.

Enjoy an afternoon of live piano music with Nina Newton at Isabel's Bar.

Blending island-inspired melodies with acoustic favorites, their performances provide the perfect backdrop for a leisurely relaxing breakfast at Lighthouse.

Kick off the week with a refreshing favorite. Every Monday from 2:00 PM to 4:00 PM, enjoy Buy One, Get One Margaritas and Mojitos at Isabel's Lighthouse and The Bungalow Bar.

Celebrating all things fantastical, this legendary Key West party lasts for 10 days and dates back to 1979. This year's theme is Musical Icons & Iconic Musicals.

Ease into the island’s rhythm with live jazz and folk music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

Celebrate Key West’s Bahamian heritage with Caribbean music, Junkanoo traditions, island flavors, arts, and community spirit at the lively Goombay Festival in Bahama Village.

Ease into the island’s rhythm with live jazz and folk music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

Shop local art and handcrafted finds, enjoy food, drinks, and live music at the Key West Artisan Market’s Fantasy Fest edition near Higgs Beach.

Greatest Hits Pool Party takes center stage during Fantasy Fest at Winslow's Bungalows. Come dressed as your favorite music icon, sing your favorite hits during poolside karaoke, dance to live DJ sets, and compete for Best Dressed and Best Performance.

Kick off Trop Rock N' Duval with Mick Fury as he brings his signature blend of rock, blues, Americana, and island favorites to Winslow's Bungalows for an unforgettable afternoon of live music.

Spend the afternoon with Reggie Starrett as he brings a mix of acoustic favorites, easygoing melodies, and island-inspired sounds to Winslow's Bungalows during Trop Rock N' Duval.

Join Ricky Lamb for an afternoon of original music, classic hits from the '60s through the '90s, and the laid-back Trop Rock sound that captures the spirit of Key West.

Start your morning with live music from Wichita Jack at Isabel's Lighthouse. A solo musician based in Key West, Wichita Jack brings a laid-back blend of rock and roll inspired by artists including Eric Clapton, Tom Petty, Pink Floyd, Paul Simon, Jim Croce, Bob Dylan, and more.

Enjoy an afternoon of live piano music with Nina Newton at The Bungalow Bar at Winslow's Bungalows. Blending timeless melodies with contemporary favorites, Nina's performances create a relaxed backdrop for a leisurely afternoon in the heart of Old Town.

Close out Trop Rock N' Duval with Dave Freeman & Friends as they perform a lively mix of original music, coastal favorites, and classic hits that capture the easygoing spirit of Key West.

Keep the party going after Mangoes Brunch 'Drag Royale' with Drag Me to the Lighthouse, a lively meet-the-queens afterparty at Isabel’s Bar from 3–5 PM.

The World's Fastest Boat Parade brings the excitement of offshore racing to the heart of Old Town as race teams and their powerboats make their way down Duval Street during the Race World Offshore Key West World Championships.

The Race World Offshore Key West World Championship returns to Truman Waterfront Park, bringing the world's fastest offshore powerboats to the waters surrounding Key West for the final race of the national series.

Celebrate the season as beautifully decorated boats illuminate the Historic Seaport during one of Key West's favorite holiday traditions.

Celebrate Key West’s literary legacy with acclaimed authors, engaging conversations, readings, and writers’ workshops at the annual Key West Literary Seminar.

Trade winter for sunshine and ocean views at the 2027 Key West Half Marathon & Runfest, featuring four races and a full weekend of island celebrations.

Five days of Red Dirt, Americana, sunshine, and island energy come together for Mile 0 Fest Key West, celebrating its 10th anniversary in 2027.

Five continents, incredible wines, celebrated chefs, and global flavors come together for five unforgettable days at the 2027 Key West Food & Wine Festival.

Taste the Florida Keys at this waterfront celebration of fresh local seafood, live music, island culture, and the community behind the catch.

Declare your FUN-dependence during 10 days of parades, pirates, live music, waterfront celebrations, and wonderfully Key West traditions.