Key West

At one point or another, you’ll see the bits of nearly every guest at Island House. After all, it’s a men-only gay hotel with a clothing-optional policy designed to free you of that tacky tropical wear you thought would be the norm in Florida. So while you won’t necessarily get lucky with anyone, you’ll definitely be treated to some eye candy. As one regular visitor told me, “you’ll attract more attention if you aren’t naked at Island House.”

Island House is an icon of Key West’s popularity as a gay men’s destination; its clothes-free attitude is a reflection of the similarly relaxed vibe at some bars on and around Duvall Street, and proof that this once-secessionist little island is one of the most permissive gay destinations in the United States.

Since flights into Key West’s airport are limited, my partner Angel and I flew into Miami International Airport and rented a car, making the nearly 130 mile scenic drive south along the Overseas Highway, with a couple quick stops for gas, photo opportunities and refreshments. Upon arrival, a friendly reception clerk checked us in and gave us a quick tour of the hotel while two guys took our bags to the room.

Open since 1976, Island House bills itself as the longest continuously-operating men’s guesthouse, and the current owners — a gay couple who bought the property in 1999 — have spent an estimated $2.5 million on renovations over the past decade, introducing high-quality mattresses, flat-screen televisions, digital cable service (which includes three free porn channels), free WiFi and custom-made furniture. The adult video lounge — which has a back room and a hall of mirrors — is the most recent to undergo renovation. All guest rooms are air-conditioned and equipped with rather upscale amenities.

The architecture of the property is classic 1890s Key West style. Over the years, the buildings that make up this compound-like property have served as private residences, a boarding house, a laundromat and even a cigar factory — a nod to the island’s once-tight cultural links with nearby Cuba. Today, the hotel is home to a variety of modern features, including a small but well-equipped gym with shower area and indoor Jacuzzi, with vaguely Greco-Roman wall murals as well as a sauna and steam room.


Near our room, men of various ages — in various stages of dress — bobbed about the large, palm-fringed swimming pool, chatting and making quick dashes to the poolside bar and restaurant, which is open 24 hours a day. The disco ball hanging innocuously above the pool was another unsubtle hint that this was a gay hotel.

“Be sure to go to the bar at happy hour,” the clerk advised as he dropped us off at our room. Our accommodations were in the KP2 Pool category — a deluxe poolside room with private bath, two queen beds, a desk and a wet bar/kitchenette with mini-fridge, microwave and coffee maker. The earth-toned décor was soothing and tasteful, with lots of throw pillows. Compared to my last clothing-optional hotel experience, this was like staying at the Westin.

A pair of artistically coiled sarongs lay on one bed, ready to become our resort wear while on the property. We grabbed the hotel’s Aveda bath amenities and took quick showers before changing clothes and heading downstairs for the first of the nightly happy hours — Angel in sexy Speedo-style swimwear, and I in my puffy Walmart finest and an unflattering aquatic shirt, to protect my pasty, redheaded-vampire skin from the sun.

Happy hours are big draws for many bars and hotels, and at Island House it’s an especially attractive proposition, since it includes an open bar with a variety of alcoholic beverages for both hotel guests and visitors who’ve paid for a daily or weekly pass. From 5:30 to 7pm every night, the bar, café and pool area are packed with happy, socialising vacationers and locals. That first day, we divided our time between the bar area and the bathtub-warm waters of the swimming pool, where blue noodle flotation devices and floating lounge chairs made it easier to stay in the deep end while imbibing.

We quickly noticed that Island House attracts a variety of gay men — for the most part, a mish-mash of US types from around the nation, with some visitors from other countries as well. Ages varied widely, and the ambiance was more jovial and festive than cruise-y (although several repeat visitors advised us that the video lounge, as well as the hot tub in the other courtyard, were the cruising areas of the hotel).

We spoke with a variety of friendly types: a South Asian guy in a red, box-cut bikini who was raised in Scotland, taught college in Ithaca and now served as a professor of religion and sex in south Florida. “I needed to get away alone, get away from work,” he explained as he sipped a cocktail. “I was a bit nervous when I arrived, so I said to myself, ‘let me have a drink,’ and now I feel fine.”


Indeed, Key West’s friendliness and randiness is fuelled to a certain extent by booze, and its nudist leanings are part hippie-style freedom of expression and acceptance and part cruise-y, in-your-face sexuality, as evidenced by the guy at the bar who enjoyed pulling my boyfriend’s Speedos down every time he walked by.

We also spoke with a trio of transplants from Syracuse, Buffalo and somewhere in Michigan, whose stories I honestly can’t remember due to the two and a half hour open bar. I do recall, however, that they explained why locals love Island House: the membership and day passes. “You can pay one fee and use the gym, the pool and even enjoy the happy hour with free drinks,” one guy explained. Happy hour at Island House also serves as an opportunity to find out about local nightlife; just after our conversation, two tall drag queens teetered in to distribute flyers, promoting a drag show that night at a nearby gay bar.

Happy hour segued into dinner, and I nursed a giant Kahlua with milk, accompanied by a tasty Angus beef burger while Angel guzzled a Red Stripe and nibbled at a plate of Buffalo wings. The food was better than we expected, and the strong (and free) WiFi allowed me to catch up with some work just steps away from cavorting nudists.

That night, we took a 15-minute walk to go bar-hopping, and came back to find the after-dark pool scene considerably quieter, with the disco ball glistening over the warm waters as a few men quietly chatted. We changed in our room and went to the pool for a nightcap, while striking up conversations with several guys, including a couple visiting from the northeast who’d never been to a gay hotel before. “I’ve been working out for months just so I could go naked while I’m here,” he told us. The following night, we’d join them for dinner onsite, with two members of our party dining in the nude.

On our final day, we took one last dip in the pool and spoke with a guy we’d seen the night before receiving a blow job at a bar called Saloon. He was nude again today, but solitary, relaxing in the pool and wearing a hat he told us he’d fashioned after one worn by a homeless guy with whom he used to have an ongoing sexual relationship. When we told him we were about to drive back to the airport in Miami, he advised us: “You MUST come back for Fantasy Fest. It makes Mardi Gras in New Orleans look like kid stuff.”  

GT stayed Island House, Fleming Street, Key West, Florida,

Words Mark Chesnut 



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