Unusual & Unique Places to Stay in Florida

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Sometimes you just want a hotel. Clean room, decent bed, job done. But every now and then, it’s nice to stay somewhere with a bit more personality. The sort of place that makes you go “oh wow” when you arrive — and makes your photos look 10x more interesting.

Florida’s full of these kinds of stays, if you know where to look. Not the usual high-rise resorts or standard villas (as great as those are). We’re talking treehouses, boats, retro motels… that kind of thing. A little bit unexpected.

Treehouses You Can Actually Sleep In

Yes — proper treehouses. Not just a cabin raised off the ground, but real-deal, leafy canopy hideaways. There’s one near Orlando that’s built around a big old oak tree, with a spiral staircase and everything. Bit of a drive out, but it’s peaceful, private, and feels miles away from the theme park madness.

You wake up to birdsong. Sit out on the deck with a coffee. Maybe not ideal for toddlers or if you’re not great with stairs, but for couples or older kids? Pretty magical.

Airstreams and Vintage Trailers

If you’re into the whole retro Americana thing, this is a fun one. All across Florida — especially around the Gulf Coast and northern parts of the state — there are places where you can stay in shiny silver Airstream trailers. Some have been done up beautifully inside, with cute kitchens and surprisingly nice bathrooms.

They’re usually part of small camp-style resorts with BBQ areas and hammocks. One near Santa Rosa Beach has a firepit circle where everyone sits around at night with drinks. Slightly hipster? Maybe. But fun, for sure.

Disney Cabins That Feel a Bit Like Wilderness

Now, this one’s technically still within Disney World. But it’s not your usual resort. The cabins at Fort Wilderness are tucked into pine trees, with wooden porches, bunk beds, and little kitchen areas. You still get the Disney perks, but it doesn’t feel like you’re right in the thick of it.

Some people stay here and don’t even go to the parks every day. They just bike around, spot deer in the mornings, roast marshmallows in the evenings. It’s not for everyone, but if you want a mix of nature and theme park magic, it’s an interesting option.

Sleep On the Water — Literally

Over in the Keys, you can rent floating cottages or houseboats. Not massive yachts, just cosy little spaces that bob about gently. Some are moored up at marinas, others are a bit more adventurous.

You’ll want to check for air-con (some don’t have it — huge mistake in July) and parking. But if you like sunsets, and the idea of waking up with water all around you, it’s a bit of a showstopper.

Old-School Florida Motels (With a Makeover)

These are a bit hit and miss — but the good ones? Worth it. You’ll find renovated motels that have kept their original neon signs and 60s layout, but inside it’s all modern touches and pastel walls.

There’s one in St. Augustine that’s got beach cruisers out front and a little coffee window round the side. Feels like you’re in a film. And way more fun than a bland chain hotel.

You don’t have to go quirky. Standard hotels are easy. But if you want to try something different, Florida’s got plenty. Some of it’s surprisingly affordable too — especially if you’re booking out of season or staying just a night or two between bigger stops.

And hey, even if you think you’re a “stick to what you know” kind of person… it might be fun to surprise yourself.

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