My friend and fellow historian Joey Vars and I recently gave a talk about historic hotels in Florida where people can book a room and spend the night. The talk proved popular, garnering an encore performance at OLLI at Eckerd College. That second session also filled up fairly quickly, and I promised those who attended I’d list the hotels and their booking information in a post they could reference.
Below you’ll find a list of Florida’s historic hotels still welcoming overnight visitors. The year next to each hotel denotes the year the hotel opened for business.
Right next door to tourist-swollen Kissimmee, you’ll find St. Cloud, where filmmakers made this delightfully bad film — from which 10,000 Maniacs got its name — in 15 days. Stop by St. Cloud, an area with some fascinating history, and don’t forget to eat at The Catfish Place. Watch the trailer.
Take one mad scientist, a catfish, and a human, and what do you get? ZAAT. Filmedin Green Cove Springs, a small town on the St. Johns River well worth a visit. It’s a beautiful Florida town that evokes whispers of yesteryear. It’s changing rapidly, though, so go see it now. At Christmas, they have an annual Parade of Trees, a mailbox with a direct line to Santa, and Christmas on Walnut Street. Watch the trailer.
Grew up in Florida in the 1980s? This is so your movie. Seriously. Hungry? Go grab a bite to eat at one of Orlando’s amazing restaurants. Rick suggests Hot Dog Heaven, which opened around the time the film hit theaters. Watch the trailer
To call Stock Island “the Key West you never knew” may sound dramatic, but it’s the way I’ve always pictured Key West before, as my husband likes to say, Dunkin’ Donuts came to town.
Don’t get me wrong, there’s a lot to love about Key West (its history, art, and architecture come to mind) — but there’s also a lot I cannot abide (the Duval Crawl, the cruise ships, and the drunken smell that tends to linger well after the bars close, to start).
However, right before you get to Key West, there’s an overlooked key that has all the trappings of a truly special place: Stock Island. With not too many places to stay but a lot of gritty reality — not to mention some fantastic artists who live and work there, Stock Island’s easily one of my favorite places in the Florida Keys.
I’ve read several accounts of the origin of the island’s name, but the only Florida Keys historian I trust — Brad Bertelli — tells me the island gets its name from the one-time practice of keeping livestock penned on the island. Brad has a wildly popular Facebook group devoted to Florida Keys history. He posts about history throughout the Keys, and has a few posts showing historic images from Stock Island.
In more recent history, Stock Island has some interesting lore. In popular culture, it gets a bad rep as a place to dump a body. The late Tom Corcoran placed at least one body there (in his books, not in real life), and he’s not the only one. Compared to Key West, Stock Island isn’t pretty — at least, not in the conventional sense.
But, as Key West fell victim to its own popularity and the slices of genuine Keys life grew smaller and smaller, something happened on Stock Island: it took up where Key West left off. I have no idea whether this is a well-planned marketing campaign, something organic, or a little bit of both.
And you know what? I don’t care. While I realize this isn’t 100% true, Stock Island reminds me of the Key West that once was. Maybe it’s more accurate to call it the Key West that could have been.
What to Expect When You Visit Stock Island
If you visit expecting a smaller, less-crowded version of Key West, you will be disappointed. While the island has no shortage of things for tourists to experience, it’s largely populated by working class people. In the lower Keys — especially close to Key West — working class lifestyles look nothing like working class lifestyles in the rest of the country.
Most of the homes here are mobile homes with little or no yard.
Real estate costs money and money isn’t something the people serving your food, making your bed, and selling you t-shirts have in abundance. (Consider that the next time you tip, too — will it really hurt you to leave 25%?) If you really want to pull back the veil on what living in the Florida Keys looks like for the average person, take a look at the neighborhoods on Stock Island (but remember, this isn’t Disney World — these are people’s homes. Show respect and don’t walk onto anyone’s property or take a bunch of photos.)
You might think some of the neighborhoods look like a third-world country. They aren’t.
Odds are, many people reading this can’t afford to rent one of these trailers on what they make (2023 rates hover around $3,000/month for a one or two bedroom). Even when you do own, when you know it could get washed away every August, you don’t have a lot of incentive to go full Property Brothers.
The tourist areas don’t look like tourist areas.
Case in point: one of the best restaurants on the island, Hogfish Bar and Grill, is right by a bunch of those trailers that may make some people clasp their pearls, swoon, and double-check the locks on their Lincoln Navigators. El Siboney — one of my favorite places to eat here — has a sign that looks as though it could be one of the first neon signs, anywhere, ever. And, while The Perry and adjacent marina don’t look like most of the rest of the island, the drive to get there is decidedly un-touristy. This is what makes Stock Island worth the visit. This is pure Florida Keys, warts and all — and remember, every home you pass is someone’s iteration of paradise.
But hey, you want to see the real Florida Keys, right?
This is it, baby. Stock Island is as real as it gets. Soak it in. It could be gone before you know it.
Walk behind Hogfish to meet the locals (and see some great art)
Take your morning run through the neighborhood, where you can see how locals without a gazillion dollars really afford to live in the Florida Keys
Places to Eat
El Siboney. This place has fantastic puerco asado, among other things. They have a full liquor bar, plenty of seating, and a cadre of locals who eat here.
Hogfish Grill. If they have kingfish and grits on the menu, get it. Trust me.
Matt’s Kitchen. The only bad thing about this is that it’s a fantastic restaurant in a hotel, so, yes, it’s a little more tourist-oriented. But the marina at The Perry has liveaboards aplenty, so you’ll still get local flavor here.
Places to Stay
The Perry’s one of the nicest, newest hotels on the island, and I love staying here.
Boyd’s Key West Campground is popular (including with fellow road tripper, Jon Kile) for its proximity to Key West. If you don’t mind a lot of people in a relatively small space, this may be a great option. It comes at a price, though: Camping shouldn’t cost this much. Ever.