The Gay Guesthouse Goes 21st Century: Key West's Island House

The country's longest-running gay guesthouse and resort, Island House first opened in 1976, the 39-room Island House continues to be an oasis of freedom and clothing-optional fun for gay male travelers of all generations thanks to utterly modern 21st century upgrades, amenities and services that best any resort (and no "resort fee"!). These include a daily open bar from 5 p.m. - 6:30 p.m., free parking, complimentary WiFi, Starbucks coffee and TAZO tea, Aveda bath products, custom sarongs, and, for frisky alone (or not-so-alone) room time, three 24/7 channels of all-male adult films.

Island House's Director of Marketing, Jeffrey Smead, first experienced the property as a guest in 2005, fell in love with it, and joined its team in 2011. Here he delves into the history of the "gay guesthouse and resort" concept, changes over the years (there have been five owners, with the most recent changing of hands in 1999), and what makes Island House perfect for gay millennial newcomers and longtime visitors alike.

How would you describe a gay guesthouse and resort?
The concept has grown since the 1980s. It's gay-owned and operated, that's the main prerogative. Guests come here for vacation and want everything they'd typically get in Florida, but also appreciate that it's clothing-optional, an all-male clientele, and a laid back, relaxed environment.

Island House offers that sanctuary feeling that this is your special place and getaway. A sauna, video room, massage pavilion, indoor and outdoor hot tubs -- what everyone wants with a gay twist on it. Since 2016, people are trying to escape the news, too. It's had such an effect on everyone's psyche. The fact that it's gay-owned and operated is the number one thing, though.

How does Island House fit into Key West's LGBTQ history?
We've been coined the "original LGBT destination" and we're a product of people's sensibilities in the 70s and 80s, which had a snowball effect in the following decades.

Key West was somewhat isolated and undeveloped in the sense that there wasn't the tourism boom like we've seen over recent years, as the gay community started moving here and buying these old houses built by shipbuilders. It started out as inexpensive and bohemian - come to Key West and have a crazy time with gay people! The AIDS crisis played a huge part, too. A lot of people were told they didn't have much time left, so they thought, "If this is the end for me, I'm going to do it in a place people love me." In the 80s and 90s, there were nearly thirty gay guesthouses in Key West, most of which were all male.

Are millennials coming to Island House, and what's attracting them to a gay guest house versus a mainstream hotel or Airbnb?
If you've never stayed at an all-male lodging establishment, you have to try it at least once. I challenge anyone to find a place that has these three things: full bar, full restaurant, and nudity. You really can't find this anywhere else as far as licensure.

There's a magic that you have to experience. I've seen millennials come through the door and they're often shyer and don't want to get naked. After they relax a bit things unfold naturally and they wonder what they worried about, and they're like, "I get it now."

Island House has managed to be contemporary yet retain the elements that keep people coming back over the decades. What can you say about that?
You can't rely on a rainbow sticker anymore. You have to be good as well as gay. We're always working on things to be in the best condition, but you also have guests who say "please don't change that."

We have new Philippe Starck barstools. You won't see any wicker around here! It's not an old-time, ancient establishment. Everything is very sleek and well thought out. And we're not going to offer a cellophane-wrapped muffin for breakfast. We have a restaurant -- do you want lobster benedict or shrimp and grits?

What's this about a group of Andrew Christian models getting a firsthand Island House experience?
They shot one of the first videos here for Pablo Hernandez and Murray Swanby, two of the more well-known AC models that made a real name for themselves. In 2013 we had 18 Andrew Christian models, all between 21 and 23 years old, and none had been here before.

When they arrived from L.A. on a redeye, they were like, "What's so great about this place?" It took about six hours before everything changed and they thought, "Oh my gosh this is an adult playground." It disarmed them. When in Rome or Key West, get on the bandwagon. It was a funny transformation of them thinking they had to keep up that WeHo image to "Alright, this is going to be like summer camp for five days" and they were into it.

Ready to plan your own Island House getaway? Visit IslandHouseKeyWest.com.

Sponsored content.