Monday, March 4, 2024
InterviewsTravel

Meet the new team of Island House in Key West

Island House, the popular clothing optional resort in Key West, is now under new management!

Island House is an award-winning gay resort in Old Town Key West, set in a completely secure private compound where the choice to wear something (or nothing at all) is yours! We recently had a chat with Jeff Smead, the founder of Island House Management, to discuss what guests can look forward to is this exciting new chapter!


Kyle Jackson: Can you tell us about your management company and how it got started?

Jeff Smead: My husband James Braun and I founded Island Mates Management (IMM) in 2021. We wanted to create a hospitality management company that catered specifically to gay businesses. So many owners of gay establishments are limited to hiring their management and putting them on their own payroll.

Jeff Smead & James Braun

We wanted to be an alternative to that, in a way that allows major concerns of hospitality owners to be put as ease. Whether it’s a gay resort, a gay bar, a gay restaurant, or a gay charter company, we want to be that solution for owners of major gay brands to become our next clients.

KJ: When did you begin managing Island House and how did that come about?

JS: I had worked for Island House as Director of Marketing for 10 years up until the pandemic hit. A few months later in December of 2020, the founding owner of Island House (Jon Allen) passed away, and his surviving husband (Bobi Lore) became the sole owner of the resort.

In March of 2021, Bobi contacted me wanting to learn about how we might come together and make something work. We met for coffee the next day, and I asked him to give me roughly one week to get prepared, and that I was going to pitch a big idea to him. Bobi seemed quite open minded and very supportive, and so about a week later, James and I presented Bobi with the concept of Island Mates Management, complete with a clear understanding of what that specifically means, and how it could work to the benefit of a property as unique and special as Island House. Long story short, we got the keys to the resort on July 28th, 2021, and we’ve been full steam ahead since then!

From left: Bobi Lore, James Braun & Jeff Smead
KJ: What are some of the key events happening at Island House this year?

JS: We’re super excited about Key West Pride this year, simply because the past two years have been either cancelled completely, or only a smaller version of Pride without any of the bigger spectacle events.

So, the first week of June will be amazing for Key West Pride, with the biggest float in our history planned for the pride parade. Summer is just as popular as high season these days, and with events like Bone Island Weekend in July, Tropical Heat in August, and Labor Day Weekend in September, we have a LOT of hot naked fun planned for our guests! 

KJ: What can guests look forward to when they stay at Island House?

JS: Island House is what you make of it. You can be a social butterfly and be the life of the party, OR, you can be a total recluse and simply enjoy the sanctuary. There’s not many places where you can just walk inside and become part of an instant community, so Island House is pretty special in that sense.

We’re not the “god’s waiting room” stereotype that a lot of gay resorts get labeled. We appeal to every kind of gay man, and we love when people tell us “I didn’t expect this place to be so classy.” There really is a way to successfully pull off being all-male, clothing optional, AND classy. And Island House does that without any stretch of the imagination.

KJ: What new plans, if any, do you have for Island House?

JS: Island Mates Management has some BIG news, and we are thrilled to be able to talk about it! My husband James and I just last week went under contract to purchase the historic triplex “mansion” right next door to Island House! We close on June 3rd of this year, and we have some really big plans for the property. We will be relocating the main structure back to it’s rightful historic location to the front of 1117 Fleming St, and then converting the home to a single family unit, where James and I will live full time.

Once converted to a single family, we will utilize the other two units licensed to the property to build a brand new construction duplex building in the back yard which abuts Stickney Lane.  There will be a pool in between the two structures creating a big, shared back yard, and Island Mates Management will then brand the two monthly rentals as “Island House Villas.”

The hotel will act as the booking engine to reserve the Villas, which are perfect if you’re looking to experience Island House for an extended stay. They will be a minimum 28 day rental for these units, along with private parking, private outdoor space, a pool shared with only the Villa owners and one other Villa, and 24/7 access to Island House next door through a hidden gate. We are so excited for this next chapter for our company, especially how it has perfect partnership with Island House to only benefit the greater good of the resort.


Island House will be one of the host hotels for the return of Key West Bear Weekend this year!

The dates have been set for November 2nd through 6th, 2022 — Be ready for a HOT fall! Keep your eyes open, ears peeled and paws ready by following Key West Bear Weekend on Facebook and visiting the website to keep up with the latest news, including events, parties and more! Tickets are on sale NOW!

Kyle Jackson

Kyle Jackson is an educator, writer and actor currently spending the bulk of his time between New York, New York and London, England. He is an active member of both the bear and leather communities and is a proud member of the MidAtlantic Chapter of ONYX.

Kyle Jackson has 80 posts and counting. See all posts by Kyle Jackson

Leave a Reply

Your email address will not be published. Required fields are marked *

I accept that my given data and my IP address is sent to a server in the USA only for the purpose of spam prevention through the Akismet program.More information on Akismet and GDPR.

This site uses Akismet to reduce spam. Learn how your comment data is processed.