By Tony Adams
Jeff Smead and James Braun, partners who both live and work together, love Key West for what it affords them: a life in a gay paradise. And the island loves them for what they bring: energy, renovation skills, and an appreciation of local history fused with a vision for the future, preserving and enhancing all that is good about Key West. The duo not only serves as co-general managers of Island House Key West , but are also the proprietors of the adjacent newly opened “Island Mates Manor.”
James designed and built the components of the recently renovated Island House and did the same for the property the couple acquired and transformed next door. Even though the powers-that-be in Key West know and respect the two men, having seen their work on two earlier home renovations in Key West’s Old Town, the process of transforming a very old house, and building two rental units with a secret door leading into Island House so that their guests have private access to the resort, is daunting. A high level of trust among James, Jeff, the city of Key West, and owner of Island House, Bobi Lore, was the essential element that brought their project to fruition.
The most amazing part of this project is that they brought it to dazzling completion while planning and directing the yearlong 50th anniversary of Island House with its array of fabulous events filling the calendar throughout 2026. While most come to Key West to relax, Jeff and James are supercharged.
Jeff says, “The purchase, development, and execution of Island Mates Manor has been at the forefront of the last four years for me and my husband, James. Beyond that door next to Island House Café awaits another world – an extension of the Island House ‘experience’ that delights in the roots of gay Key West. It’s like your own private Island House, directly connected to the main resort.
“James and I purchased the dilapidated Fleming Street property adjacent to Island House in June of 2022 with big dreams for this massive 7000 square foot lot. First, it meant picking up and relocating the historic triplex back to its original location at the front of the lot, correcting an error that was mysteriously made in 1960 when they moved it to the rear of the lot. After elevating the home to our current flood regulation height and pouring a new foundation, we gutted the house from a triplex of sad apartments into a grand single-family home, built a pool and jacuzzi behind it, and then with the two displaced licenses, we did a ground-up construction of the next chapter: The Villas @ Island Mates Manor. Little did James and I know how challenging it would be to take on such a huge risk, invest everything we had into it, and bring this vision into fruition.”
Island House is itself a luxury property, but Jeff and James wanted to go beyond what the resort offers. Jeff says, “The Villas are an elevated experience for gay men who want a luxurious refuge during an extended stay in paradise. They are directly connected to the resort via a private locked gate with biometric access, offering a crazy level of exclusivity. We rent each of the two Villas on a monthly basis, with many of the highly sought after months booked with guest deposits well before we even finished construction. Literally ten paces from your Villa door, you can enter the pool area and café of Island House, giving you the party atmosphere that our guests love. You can mingle with new friends at pool parties and invite them over with you to the Villas to swim, sip, and play. It really is like Narnia!”
Back at the ranch, as it were, Jeff takes a moment to reflect on the “50 Years of Fabulous” celebration at Island House. He says, “Our 50th Anniversary set a tone that I won’t soon forget. The most enjoyable part for me was on Saturday evening during the ‘Island House Awards’ session. There I was standing poolside with a microphone, being showered with love from a group of men who represent the last 50 years of Island House success. Seeing special guests hear their name get called to receive an award and share their sentiments was especially rewarding. We were surrounded by friends and confidants, all while hosting an army of gays who relished the spirit of old Key West nostalgia, shared experience, and living history. I didn’t expect to choke up when I announced Levi Poulter & Leigh Bates for their poolside award for being the ‘face’ of Island House marketing for the last few decades. Watching people be recognized by surprise is such a heartwarming experience, especially since I’ve spent so much of my career working closely with those special men. I will always remember how good that made me feel to be the steward of Island House in that moment, and of the Key West I’ve always known and loved. The next 50 years are in our sights. We have to keep polishing this resort from the structures themselves to the guest experience. Managing this place is a huge weight to carry for gay Key West, and our goal above all is to keep the Island House experience intact and ensure it stays what it is for decades to come.”
During one of the many post-happy hour tours of the Villas that Jeff and James are always glad to provide, Jeff continues to describe the excruciating construction process. He says, “James and I have done a number of home renovations in Key West, but we knew that a multi-family property like this one would really test our limits. Our earlier projects were small conch homes in Old Town. We learned about pulling owner-builder permits, working our full-time jobs from M-F and using each weekend to tackle our project. We lived like boy scouts camping in those homes while they were built one weekend at a time. The scope of work we dreamt up for Fleming Street didn’t allow us that luxury of living inside the mess. Not to mention, it’s rather intimidating to bite off a piece of Key West located on what’s known as ‘Millionaire’s Row.’ This is the ‘hot chick’ block of Fleming that is easily visible to anyone who drives in Old Town. It felt like four years of everyone watching our every move because the mysterious ‘Addams Family mansion’ finally had new owners with big ideas. We got to know the daily dog walkers, the delivery folks, and, of course, the hundreds of gay men traversing Fleming Street to get to the gay bars on Duval. It was far different and on a scale beyond what we were used to. As a couple I don’t think anything has tested us so much as this. Obtaining permits alone in the historic district of Key West is like an act of Congress, let alone agreeing on design aesthetics.
“ When Jame and I met in 2012 at Island House – table 3. He shared that he was fairly handy and that he took some years of furniture making back in his stomping grounds of Chicago. Then we bought our first project on Olivia Street on the Key West Cemetery, and he let it rip. With no real formal training, James has this unbelievable ability to learn how to do impossible things by scouring the internet, watching YouTube videos on repeat, and asking millions of questions. He’s fearless. Whether it was design software mastery, tools and carpentry skills, or all-around impeccable taste, he does it all so well. He had an active role in every aspect of this mammoth project, to the point that our legally required general contractors were blown away that the homeowner had this level of savvy. James was on site daily before the team even showed up, and stayed late into the morning hours – for four years. It was his passion project, the driver of his ambition, and his signature mark on Key West. I’ve never met a more productive human being than James Braun. I definitely can’t keep up with him. However, I am particularly suited to sweeping up after him in more ways than one.”
Both Villas are finished, have their certificates of occupancy, and are ready to welcome guests in their inaugural year. Each Villa has two king suites, as well as a powder room on the first floor by the pool, chef’s kitchens, expert level woodwork and millwork, and amazing levels of integrated tech. Each Villa has two covered parking spots, private entrances, and balconies off every bedroom. The split-level design with three floors, offers unparallelled privacy and luxury. They are equipped with split king beds that are motorized, thermostatic showers, TOTO Washlet bidets, full laundry, and even a dedicated office space for those working while on vacation. The finish levels were inspired by Jeff and James’ trips to Dubai, Bali, and Thailand; including Armani-inspired glossy walnut cabinetry, 3D feature walls, linear light installations. The Villas are a clothing optional paradise for gay men – the first new addition to gay Key West lodging in over 25 years.
Jeff says, “James and I are ‘lifers’ in Key West, with fierce loyalty to our market and an honest desire to share its special vibe with those who come to stay with us.
“We both tend to lean into a modern aesthetic, and that’s where the Villas shine. From the outside, they look appropriate for the historic district with full width porches and hot tin roofs. But they are built like a fortress for resiliency, made completely out of concrete with all impact windows and doors. Inside, you can tell that this was designed and built by gays, specifically for gays. Monochromatic colors with slick surfaces and leather texture. Linear lighting can be found throughout, with showstopper installations above the kitchen island, task lighting, and headboards. James went wild selecting ultra-modern fixtures with a generous level of custom walnut millwork, and Dade-county pine. Even the stair treads are made from the reclaimed Dade-county pine we pulled out of our front house during renovation. We would dumpster dive each night wearing headlamps to find the pieces we could salvage for special projects like the stairs. The effort put into those elements shows through as if it was all planned from the very beginning. The heated saltwater pool offers two ledge loungers where you can sit your butt in the pool and doze off, all while the water luminaries flow lighted rays of water effortlessly by your feet. The pool deck is picture frame Brazilian Ipe wood, enveloping the swim-up bar and six-man jacuzzi. There’s formal outside dining underneath a Pergolux mechanical pergola, and modern LED lit umbrellas that set the vibe for nighttime.
“After four years of non-stop stress, problem solving, budgeting, and endless impossible tasks, we are finally here to meet the moment. Right now, we need gay spaces like this to remind us how to enjoy our lives when the world seems always to be on fire. This project represents a loyalty to Key West and its long history with the gay community, a modern take on today’s island living, so it’s only appropriate that a gay couple from Key West that came from nothing could pull it off. You’ll see signs of our personality at every turn, as we spent countless 3AMs pining over decisions that would appear seamlessly in the final design. If you’re looking for the next big thing to discover in Key West, it’s right here.
“It’s the best gay vacation rental in the world, directly connected to the best gay resort in the world. Free daily happy hour included, and no bathing suit required.”
Post-happy hour tours available on a space-available basis
