Richard Meets… Island House Key West’s Jon Allen

Jon Allen is the owner of Key West’s most famous gay resort, Island House. He purchased the hotel 20 years ago, taking a somewhat decrepit building and renovating it to bring us what we now know and love today.

I had the opportunity to talk with Jon as he and the team celebrate this amazing milestone and achievement.

Jon Allen

Richard Jones: Hi Jon, it’s great to meet you. I wanted to start by asking you what makes Key West so amazing? What was it that captured your imagination back in 1999?

John Allen: We were struck by the complete gay-friendliness of Key West, the tropical weather, and the openness of the local government to our operating a business like Island House… the concept of sex, booze, and nudity all in one place seemed perfectly reasonable to the officials we spoke to! Plus, the idea of living in Key West was very appealing!

Island House 20 years ago

RJ: What was the main reason for buying a hotel back then?

JA: We felt that we had a concept for a resort for gay men that would be very successful if we could find a suitable property.

RJ: Were there any major challenges to opening Island House?

JA: The biggest challenge was the decrepit condition of the buildings. The previous owners had not been doing necessary maintenance, so a complete renovation was needed. New plumbing, new roofs, and so much more. All of that ending up costing more than $5 million. Fortunately, we found a local bank that was willing to give us a construction loan, which we’re still paying on!

Old Island House poolside

RJ: What has been the biggest change you have seen in Key West/Island House over the years?

JA: Key West has become much less isolated due to the introduction of high-speed internet, reliable cell phone service and non-stop jet flights to major cities including Atlanta, Miami, New York, Charlotte, Chicago, and Dallas.

RJ: What is the secret to the success of Island House?

JA: The concept of the business itself is very appealing to gay men. But the real secret to our success is our outstanding customer service.

RJ: Do you have any favorite stories from all the years… that you can share?!

JA: I have many, but one I can share is from the early days, when I was answering the reservation phone line and was surprised to find a woman on the other end of the call. I explained politely that Island House was a male-only property and that we would not be able to let her stay. She said “I know that honey, I’m calling to make a reservation for my husband. We have an arrangement. He treats me right and he gets two trips a year to Island House. We’re both very happy.” It made me happy that Island House was a factor in their happy relationship.

RJ: You’re entering your 20th year of operations. What do the next 20 years look like for Island House?

JA: I’m committed to Island House surviving me as a successful clothing optional resort for men. My husband Bobi Lo Re, who is 19 years younger than I am and in good health, will continue to own the resort and is committed to operating Island House as it has been, with our present outstanding senior management team carrying on with what they do so well.

If you have never been to Island House, make sure you make a trip. It’s perfect any time of the year, head to to book now

Don’t forget we are also sponsoring Key West Bear Weekend, and Island House is the host hotel, so if a bear filled key west trip sounds like fun then head to

Key West Bear Weekend 2017

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Richard Jones

Richard is the Co-Founder of Gray Jones Media, the parent company of Bear World Magazine, and was the magazine's creator and editor for its first three and half years. He is busy developing the business in many other directions, but loves coming back to contribute when he can.