The Key West
Annual Headdress Ball 2026

Address: 526, Angela Street, Key West,

• Boutique hotel wrapped in tropical gardens.
• Polished rooms and private porches.
• Heated pool, koi ponds, and quiet corners.
• Self-serve wine gallery and live jazz nights.
• Steps to Duval, peaceful once inside.
• Website

Address: 419, Amelia Street, Key West

• Adults-only guesthouse in Old Town.
• Studios and suites with kitchens.
• Leafy courtyard and relaxing pool.
• Porches or balconies in many units.
• Easy walk to Duval, calm at night.
• Website

Address: 819 Simonton StreetKey West

• Adults-only inn in lush gardens.
• Historic cottages and bright rooms.
• Courtyard pool and hot tub.
• Light breakfast to start the day.
• Close to Duval, calm at night.
• Website

Address: 611 Truman AveKey West, FL 33040

• Modern boutique hotel near Duval.
• Bright rooms; patios or balconies in many.
• Palm-lined courtyard and mosaic pool.
• Light breakfast and on-site parking.
• Quiet base with easy Old Town access.
• Website

Address: 724 Duval Street, Key West, FL 33040

• Key West’s best-known gay bar complex.
• Pool, Jacuzzi, and men-only garden courtyard.
• Men-only, clothing-optional garden bar with go-go dancers.
• Go-go shows, drag, and video DJs nightly.
• Fun, friendly crowd and strong drinks.
• Open: Daily 10am–4am.
• Website

Address: 801 Duval Street Key West, FL 33040

• Iconic gay bar and cabaret on Duval Street.
• Home of the World Famous 801 Girls.
• Two drag shows nightly and karaoke nights.
• Friendly staff, strong pours, full of laughs.
• A Key West institution since the 1980s.
• Open: Daily 12pm–4am.
• Facebook

Address: 711 Duval Street Key West, FL 33040

• Iconic Duval Street drag-and-dance spot.
• Aquanettes headline polished nightly shows.
• Busy bar, fast service, upbeat crowd.
• Part of the Aquaplex with sister venues.
• Easy ticketing and multiple showtimes.
• Open: Mon–Thu 2pm–12am, Fri–Sat 2pm–2am, Sun 2pm–12am
• Website

Address: 801 Duval Street Key West, FL 33040

• Classic Key West leather/bear hangout.
• Dark room, patio, and late-night crowd.
• Strong pours, cruising vibe, themed nights.
• Men-forward space near Duval Street.
• Easy hop from Bourbon Street Pub.
• Open: Daily 5pm–4am
• Facebook

Address: 504 Angela St, Key West, FL 33040

• Intimate cabaret room inside Aquaplex.
• Live drag with vocals and variety acts.
• Clear sightlines, seated show format.
• Quick bar service, upbeat mixed crowd.
• Steps from Duval; easy venue-hopping.
• Open: Mon–Thu 2pm–12am, Fri–Sat 2pm–2am, Sun 2pm–12am
• Website

Address: 504 Angela St, Key West, FL 33040

• Whimsical martini bar with unicorn energy.
• Small room, big personality, friendly staff.
• Happy hour deals and weekly bingo.
• Perfect stop on an Aquaplex night out.
• Open: Daily 2pm–2am
• Facebook

Address: 1125 Duval Street Key West, FL 330403 

• Adults-only boutique hotel, bar, and cabaret on Duval.
  Nightly vocal-drag shows in the Crystal Room.
  Piano bar vibes and a lively terrace on the street.
  Sunday Tea Dance by the pool with resident DJs.
  Good food, strong drinks, and friendly service.
• Open: The Crystal Room from 8pm
• Sunday Tea Dance by the pool 4:pm-6:30pm
• Facebook

Address: 711 Duval St, Key West, FL 33040

• Courtyard hideaway behind Aqua on Duval.
• Casual hang, quick service, strong drinks.
• Great stop on an Aquaplex bar hop.
• Daytime specials and relaxed vibes.
• Open: Mon–Thu 2pm–12am, Fri–Sat 2pm–2am, Sun 2pm–12am
• Website

Address: 724 Duval St 2, Key West, FL 33040

• Poolside garden bar at an all-male guesthouse.
• Men-only space with clothing-optional pool.
• Late hours, DJs, and a friendly crowd.
• Easy access to Bourbon Street Pub next door.
• Right on Duval, social from day to night.
• Open: Daily 10:00am–4:00am
• Instagram

Address: 900 Simonton Street Key West, FL 33040

• Late-night karaoke bar with a friendly, mixed crowd.
• Strong pours, easy prices, and quick service.
• Simple room with a pool table and TVs.
• Locals, industry folks, and visitors blend.
• Casual singalong spot just off Duval.
• Open: 12pm–4am
• Facebook