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A Lesson in LGBTQ History with Key West's Legendary Gay Resort

Island House Entrance

How Island House helped transofrm Key West into the Wild West of gay getaways. 

Since 1976, the Island House has long been a secluded retreat for gay men to be themselves. At a time when homosexuality was not accepted in the mainstream, the resort proved to be a sanctuary for the gay community. Throughout 40+ years, the resort remains an integral part of the LGBTQ experience in Key West.

Situated on Fleming Street in the heart of this tropical gay mecca, the Island House is one of the oldest operating gay resorts. Whether you're looking for a relaxed and quiet weekend away or a fun-filled, debaucherous night out, this clothing-optional retreat has something for all. Be sure to book fast, With 39 rooms, this cozy resort fills up fast. As one of this year's Stoli Key West Cocktail Classic featured partners, we took a dive into its past and the importance of the Key West gay community with Jeffrey Smead, Marketing Director with the Island House:

OUT: Let's start with Jon Allen and Martin Kay, who purchased Island House back in 1999. Did the two of them live in Key West prior to acquiring the resort?

Jeffrey Smead: Yes, they met in London where Martin was born and raised, and lived in Indonesia while working in the fashion industry. Then the couple came to Key West in search of a completely different lifestyle in the iconic gay community. As it happens, the Island House was on the market and at the time, what's the polite way to put this, it was a sh*t hole! Simply terrible!

Had the Island House been functioning as a resort prior to the purchase?

Yes, we are on record as the longest gay owned and operated all-male guest house in the world. Island House has been open since 1976.


How did Key West become such an important destination for our community, and what do you think the Island House's role was in that history?

Well it started well before Island House. Before we saw marriage equality, Key West was the original gay and lesbian destination. There was something special about being secluded on the end of the road and being able to create your own community that appealed to the younger gays of the 1970's. Prior to that, Key West was pretty much a dust bowl. All of the historic houses we see today were in shambles. As the gay population moved, they began to purchase and restore the beauty to these old, historic homes. Pretty soon we had over 20 all male guest houses on a 2x4 mile island. It was the center of it all, the wild west of gay getaways.

And even though the 2017 version of Key West is much different, the Island House is still standing. Moreso, it is growing. 2016 and 2017 are proving to be the best years in our history in terms of occupancy and our ability to attract the community to Key West, more than 40 years after it opened.

We know you guys aren't strangers to a good party at the Island House, especially during Pride season. Is there anything special that stands out to you about the relationship between Island House and the Stoli Key West Cocktail Classic?

Absolutely, let me give you a little back story. In 2013, Andrew Christian had invited me to join him in LA for the taping of the Ru Paul's Drag Race Season 5 Finale. Throughout the finale, I was seated next to Patrik Gallineaux, National LGBT Ambassador at Stoli. After talking for a while at the event, the topic of the Cocktail Classic came up and, because so many of the gay bars in Key West had become iconic in the queer community, we thought Key West would be the perfect setting for this competition.

After that meeting in LA, we brought Patrik to Island House and he immediately hit the ground running, meeting with our gay and lesbian business guild and several local businesses, and the process to start the first annual Key West Cocktail Classic began. It has become an integral part of Key West Pride.


Do you have a favorite among the group of talented bartenders participating this year?

I'm here to cheer EVERYONE on and to make sure they enjoy their visit to Key West. I want all of our Pride visitors to think the Island House is the greatest gay resort in the world and want to come back, which has proven very successful!

As a veteran to the competition, do you have any advice for the bartenders going into the final stage of this year's Cocktail Classic?

Showmanship is everything. Not only do you need to create a tasty drink, but the judges are looking for a performance. They need to create a drink with a connection to the Key West community while remaining true to themselves and the respective cities they represent. Bring your personality and your passion!

I'm confident the bartenders participating in this year's Stoli Key West Cocktail Classic will put on an incredible show. Thank you so much for chatting with us, especially during Pride season.

I hope to see everyone at the Island House in Key West for Pride!

To keep up with all of the action in the 4th Annual Stoli Key West Cocktail Classic, visit

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