Event Dates
From: Awaiting dates
To: Awaiting dates
The Key West
Annual Headdress Ball 2026
The premier gay and lesbian event of the Fantasy Fest celebration proudly returns with an epic night of costumes and prizes.
The Key West Annual Headdress Ball 2026
The Key West Headdress Ball is the premier gay and lesbian event of the Fantasy Fest celebration.
- Visiting for the event? If you are looking for a last minute deal or want a larger hotel with great amenities, check out the Key West Marriott Beachside. Alternatively try Alexander’s Guesthouse for a unique gay escape.
The 2026 Annual Headdress Ball
- Next edition – Awaiting dates, Typically the Thursday of Fantasy Fest.
- The ball begins at 8 PM. The event is held at the Coffee Butler amphitheater at Truman Waterfront Park, a 4 minute drive from the bars along Duval street.
- First Place prize is $3,000; Second Place is $1000, and Third Place is $ 500 for the best Headdresses, judged from the shoulders up.
- Proceeds from the Headdress Ball go to promote LBGTQ+ Tourism to Key West. Following the show there will be a special Happy Hour Disco Dance at the Aqua Sidebar.
- Host, djs, performers and guests to be confirmed.
The Competition
- This unusual competition allows contestants to go “head to head” to impress the audience with what they’ve got from the shoulders up!
- Over twenty five contestants will parade their Headdress creations to vie for the $3,000 first prize.
History of the event
- Over three decades ago a group of Key West business people gathered together to form the Key West Business Guild, the nation’s oldest LGBT Chamber of Commerce.
- Only a few years later during the fledgling years of Fantasy Fest, that same group started the Headdress Ball. The Ball served then, as it does now, as a major fundraiser for the Guild.
Gay Key West – Where to stay?
Most of the gay bars in town are clustered along colourful Duval Street. Check out our Gay Guide to Key West.
The following hotels are close to the gay bars and beaches:
Duval Gardens, Truman Hotel, The Gardens Hotel, Paradise Inn
Recommended Hotels
Where to stay close to all the gay bars
Our top 4 selections with the best rates.
Where we stay!
The Paradise Inn is our favourite place to
stay in Key West. Great location & service
Official Website
For further information and advice on
The Headdress Ball, visit The Website
Gay Map of Key West
Most of the gay bars in town are clustered along colorful Duval Street, in the historic district, which is also home to dozens of fun shops and inviting restaurants.
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.
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
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
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
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
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
Recommended Hotels in Key West By Booking
Book with confidence. Get the best Prices from our partner Booking.com
We have chosen hotels in Key West that keep you close to all the shops, restaurants, bars & fun
The Gardens Hotel
4 Star, adults-only
- 4 Star, Adults-Only with Two Outdoor Pools
- Close to the gay district
- Balcony or patio, flat-screen TV
- Adults-only, two pools, one-minute walk from Duval Street, rooms with balconies or patios.
Paradise Inn
3 Star, Adult Only
- 3 Star, Landscaped Grounds with Koi Pond
- Close to the gay district
- Sitting area, cable TV, microwave
- Adults-only, landscaped grounds, complimentary breakfast, suites with sitting areas and kitchen.
Douglas House
3 Star, Adult Only
- 3 Star, Near Ernest Hemingway Home
- Close to the gay district
- Microwave, refrigerator, free Wi-Fi
- Adults-only, minutes from Ernest Hemingway Home, offers free parking, pool, & microwaves.
Truman Hotel 3 Star
Trendy Boutique
- 3 Star, Trendy Boutique with Outdoor Pool
- Close to the gay district
- iPod dock, flat-screen TV
- Trendy boutique hotel, outdoor pool, modern rooms with iPod docking stations, and refrigerators.
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