Gay World Travelers Have It Right. Island House Resort Is What We Need

It’s been a hot minute since I had an amazingly gay vacation. Christmas with the family in Maine and then a “straight” Caribbean cruise with friends in March were the last two times I escaped the walls of my Florida home. Granted, yes, the area where I live, Wilton Manors / Fort Lauderdale, I’m already in one of gayest of gay meccas out there.

But you need to get away and when it comes to leaving a gay mecca because you’re looking to be in an even more gay and accepting environment, some place where you really want to embrace your sexuality, your sex, your s.e.x., where the hell do you go? I point the car south and head to Key West and The Island House.

How do you get comfortable at a place like the Island House?

The Island House Resort Key West proclaims that it is –THE BEST GAY RESORT IN THE WORLD. It’s a clothing optional all-men’s resort where you are who you are. Big, small, fat, tall, old, new, renewed, hairy, smooth, masculine, femme, hung, not, cut, uncut, pierced, tattooed, and, they’ll all be there and they all were last week. And they all were accepted. You do you, you be you, you do whomever you want to, be done by them, or do no one. 

Screen capture from Island House home page

Do you have to go naked there? Well, I’m not one to go naked in clothing optional places, that’s just me, but bravo for the ones that choose to do so. And many many went nude and others had a fashion show each day with a new suit … and then they took it off. 

What is the atmosphere like at the Island House?

I’m also not one to get excited and involved with someone else where people are going to see, but bravo for the ones that do. It’s a judge free zone as long as safety and cleanliness are maintained and other guests are respected.

With all of that said, with balls flopping around and ass cracks and Prince Alberts all over and penises in all stages of engorgement … what a fucking relaxing time! When you’re at the Island House, it’s like there is zero stress remaining in your life. You’re almost in a constant exhale for the duration of your stay.


With the immaculate and amazingly clean rooms, health club and spa, video lounge, pool and jacuzzi, and the bar and café areas, and even the sidewalks around the resort are kept swept and cleaned (we saw that attention to detail many times), Island House is so well maintained. I know I’m not the only gay that notices all the little things out of place, well, you won’t see that, I never did. 

I don’t think I captured a peen

How do you take pictures at the Island House?

It seems there is always someone naked at the Island House and maybe that helps to desensitize you to it all. Of course, some you really want to look at as they get you giddy, and others you just have to say, bravo, look at his “courage”. But there’s always peens or ass crack everywhere. So instead I took pictures of my masseuse Dave and some of the many strawberry daiquiris we ingested. Ps: the massage was great as the client is usually naked on the table with the breeze blowing through the poolside cabana. Dave used massage creams instead of oils and that was a treat!


The drinks do flow very easily and guests of the resort are able to have four (4) free alcoholic beverages during the daily happy hour. 


This was the second time I visited the Island House Resort. My first trip was a couple years ago (Travel Thursday: Visiting the Best Gay Resort In The World. The Things We Do For Our Readers) and I was more in photographer mode as well as in awe mode then. This trip was a birthday celebration and I was very grateful for my time there.  

How do you say goodbye to a place like the Island House?

After you’ve been there for 3 or 4 days, charging everything to your room, meeting new friends from all over the nation and world, it’s sobering to put more than one layer of clothing on and get in the car and drive away. 

But the best way to say goodbye to the Island House, after you’ve signed your room bill and turned in your key, the best way to say goodbye is with no regrets and maybe a plan for next time you visit. If you didn’t do all that (or who) you wanted to do, realize that everything else was amazing and the Island House will be there when you are ready to return. 

Related Post: TRAVEL THURSDAY: Trips To The Keys Are What You Make Them


And maybe, before you go, plan your next stay. You’re going to have to talk to a real person any time you book so why not right then and there. Some like to book a room on the pool deck so they can be close for swimming or for leaving their shades open to invite eyes in to watch… or maybe by the jacuzzi so shades or doors could be left invitingly open… or off to the side where you may have a little more privacy… or whatever room is open and make it work. Our 2 bedroom apartment this trip was perfect. 

How do you write about a place like the Island House? 

No, I’m not going to share everything I saw (or did) at the Island House. I’m not going to describe the other guests, who they were, what they did or didn’t do.  Some things need to stay there or stay in my memories. The joys were embraced and adulting did occur. 

But there are some bits of advice I would share:

  • Eat the amazing food. Some of the best food I’ve had in the Keys is here. The kitchen is open 24/7 and the quality is there every.single.time. Yes, the meatloaf will be the best you had, breakfast is wonderful, and the value is unbelievable. Because the food is so good, you’ll find yourself having no reason to leave. 
  • Visit all parts of the resort. You may see that some men don’t come to the pool side of the resort so you’ll miss out on meeting the sauna, gym, shower, indoor jacuzzi, outdoor jacuzzi boys. The video room has its visitors, too that may not be seen in other parts of the resort. 
  • Say hello to everyone as everyone is there for the same reason, to have a good time.  And you won’t know what level of “good times” they are looking for unless you chat. And keep talking to them as their “good times” chart may change as their stay goes on. 

Thanks again Island House and your guests, your staff, your existence. You offer a respite from the world, an escape from the norm, a celebration of us. The environment you create for your travelers is one that we all must experience to realize that we all need to be us, to be pampered, and to be happy.


Here are a couple more pictures about the Island House.

As mentioned, the meatloaf was a great choice and you can mix the sides up if desired. This pic was from my first visit.

We did head into town a handful of times, Ubers work well at around $12 for an XL and the town is great to visit, but it was hard to pull yourself away from the resort as all was there. 


This time, there were three of us so we lodged in one of the apartments at the Island House.  Here is the description of the apartment and pictures from the Island House website.


2 bedroom/1 bath apartment, located across the lane from our main entrance, and features a private entrance and dedicated off-street parking. This ground-floor luxury unit nestled inside this delightful historic home has a King bed in one bedroom and a Queen bed in the 2nd bedroom, full kitchen with island seating, and a deluxe leather sectional couch. A full sized private front porch is around the corner on the Front side of your unit, and is the perfect lodging choice for those who want some extra space, as well as the ability to travel with multiple friends on vacation.


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