Event Dates
From: Wednesday, October 29, 2025
To: Sunday, November 2, 2025
Key West Bear Weekend 2025
The Bears don’t hibernate in the Winter.. the smart ones head to Key West every November.
Key West Bear Weekend 2025
The Bears don’t hibernate in the Winter.. the smart ones head to Key West every November, for a weekend of fun and relaxation!
- Stay close to the pool parties and daytime events at Alexander’s Guest house, an adults only hotel rated “Exceptional” by guests with charming rooms and superb hosts.
The Bear Weekend
- Wednesday Oct 29th – Sunday Nov 2nd, 2025 – Events take place across Key West and are open to everyone. Some of the island’s most popular gay venues host a series of pool parties, night time events and bear gatherings.
- Island house plays host to the both the welcome event on Wednesday at 5 pm and the Farewell party on Sunday at 6 pm.
- Stay at the adults-only Porch on Frances Inn, rated “Exceptional” by guests with a perfect locations, beautiful rooms and a warm Key West welcome.
The Pool Parties
- Events kick off on Wednesday From 12 pm to 5 pm with the Bear Soup Party at Island house. Grab a swimsuit (or not!) and meet the rest of the gang with lunch poolside, cool cocktails, and new friends.
- Pool parties continue on Thursday & Friday afternoons at Island House.
- Events end on Sunday with the “Bear ASS Tea Party” described as a frisky clothing-optional shindig!
Night Time Events
- Bourbon Street Pub – New Orleans-themed gay destination for theme nights, drag shows & outdoor pool with bar & theater. The famous men only clothing optional garden pool is a true Key West experience, as are the nightly Men of Bourbon shows.
- Birdcage Cabaret – Located on Duval Street, Birdcage is a new venue, taking over the old Side Bar venue.
- Saloon 1 – Host of the infamous Saturday night Cock Shock competition. Claissic gay bar with outdoor patio and a cruisy vibe.
Where to Stay during Key West Bear Weekend?
Most of the gay bars in town are clustered along colourful Duval Street so we have found hotel that keep you close,
Duval Gardens, Truman Hotel, The Gardens Hotel, Paradise Inn
Check out out Key West Gay Guide to find the best places to dine, party and play on the island.
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 when in Key West. Great location
Official Website
For further information and advice on
Key West Bear Weekend, 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.
526, Angela Street, Key West, Monroe County, Florida, 33040
This adult-only hotel offers two outdoor pools. Duval Street is a 1-minute walk away, and Key West Butterfly and Nature Conservatory is 3 minutes’ drive from the hotel. A private balcony or patio with property views is provided in all rooms at The Gardens Hotel Key West. A flat-screen cable TV, ironing facilities, and a refrigerator
Douglas House, 419, Amelia Street, Key West, Monroe County, Florida, 33040
Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool. Free Wi-Fi is also available. A microwave, refrigerator and coffee-making facilities come standard in each room
819 Simonton StreetKey West, FL 33040
Paradise Inn - Adult Exclusive is located in Key West and features landscaped grounds with brick paths and a lotus pond with koi and tropical turtles. A complimentary continental breakfast is served in the lobby.
611 Truman AveKey West, FL 33040
This trendy Key West boutique hotel features an outdoor pool and modern rooms equipped with iPod docking stations and flat-screen TVs. South Beach - Key West is 0.8 km away from the property.
1 Duval St, Key West, FL 33040
Featuring air-conditioned accommodation with a private pool, 3 bedrooms, a TV with cable channels, an equipped kitchen with a dishwasher and a microwave, a washing machine, and 4 bathrooms with a shower.
Key West, Florida 33040
This Air conditioned holiday home includes a living room with a TV with satellite channels, a kitchen with a dishwasher and an oven, as well as a coffee machine and a washing machine. A Swimming pool & Free WiFi
Key West, Florida 33040
This Air conditioned holiday home has a living room with satellite TV, a fully equipped kitchen with an oven and a microwave, 2 bedrooms and a bathroom with shower. A swimming pool and a Barbecue. Free WiFi
Key West, Florida 33040
The holiday home includes a Living room with TV, a kitchen with a dishwasher and a coffee machine. There is a bathroom with a shower and hairdryer. A Private swimming pool and a barbecue. Free WiFi
724 Duval Street, Key West, FL 33040
The Bourbon St. Pub has been known world over for its Hot Men and Boys. And you can catch them each and every night on top of the bar for your viewing pleasure, starting at 10 PM.
The hottest men and boys come from all over the world to perform for you. Many of these hot guys want to come to the island for a vacation and while here make some extra money!
801 Duval Street Key West, FL 33040
Gay Cabaret bar, Drag shows & karaoke very popular and always busy
711 Duval Street Key West, FL 33040
Gay Night club and bar with Drag shows
801 Duval Street Key West, FL 33040Gay
Gay Male Leather & Levi Bar -with a Back Room. Everyone is welcome!
1125 Duval Street Key West, FL 330403
La Te Da, a Key West landmark with a piano bar, terrace bar, and cabaret. The best live entertainment on the island!
900 Simonton Street Key West, FL 33040Fun
Happy Hour noon till 8pm daily. Karaoke nightly from 9:30 with pool table
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.
Video of Key West Bear Weekend
Key West Bear Weekend Highlights.
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