The Middleman is Getting Rich Off Your Room Tax
And you don’t even know who’s supplying your destination Imagine someone showed up at your house, threw a pile of money on your porch, and s…
The Lodging Desk
It's no secret that I'm dating STRs. There's an economic and branding gap between the destination and the STR, and that makes my brain curly and obsessed.
It's no secret that I'm dating STRs.
There's an economic and branding gap between the destination and the STR, and that makes my brain curly and obsessed. How did we get here, the obvious gap, the players that benefit from the disconnect, the local resistance, and the traveler's insatiable appetite with STRs keep me up at night and, honestly, invigorated.
Let's get into it.
Most short-term rentals are doing the most to make visitors feel at home.
There’s the branded welcome mat. The seven-step coffee ritual. The decorative ladder that serves no functional purpose, but damn if it doesn’t say “I host.”
And still… something’s missing.
Because if your property isn’t connected to the story of the destination, you’re not in hospitality. You’re in real estate with laundry.
It’s not shade. It’s a strategic gap.
What guests actually remember isn’t how fast you texted back or how fluffy the robes were. It’s how the place made them feel about the place.
We’re at a strange crossroads right now:
STRs are outpacing hotels in local bookings
Hosts are becoming the only human interaction some travelers have
Most destinations still don’t know who their local hosts are
And most hosts don't know if they have a DMO, TDC, CVB, chamber, or some other wildly niche creature.
This week alone, we heard chamber like 17 times (and there are some that are DMOs, but that's rare). Someone else thought the DMO was just the city council. Another guessed it was “like a travel blogger for the town?”
It’s not ignorance. It’s a language barrier. A visibility gap. A trust issue. It’s the Host Gap.
(Yep, we’re naming it. Yep, we’re solving it. No, not today. But soon.)
They just launched ads for services: private chefs, massage therapists, curated in-home experiences. You can book an entire lifestyle now, not just a listing.
This isn’t a glow-up. It’s a land grab.
If you don't think that's dangerous, call me. I'll tell you a little story about how OTAs almost didn't exist without the DMO. But policy + private sector have differing appetites for risk.
Airbnb is unapologetically trying to be the destination: digitally branded, algorithmically optimized, and fully removed from any actual neighborhood soul. I cannot blame them for meeting guest demand. And they're not going to magically invite DMOs to the conversation. Per usual, we'll have to insert ourselves, loudly, and with authority.
And while Airbnb builds its experience empire?
Hosts and destinations? Still trying to figure out who the hell each other even are.
That’s not a people problem. It’s a systems problem.
You don’t need to rebrand or remodel. You need to realign.
Here’s where to start:
Would a guest know where they are just by walking in the door? Or could this listing be anywhere from Tampa to Toledo?
Your guests don’t need another coffee chain or cookie-cutter listicle. Point them to the breakfast burrito in the gas station that changed your life.
The real one. Why do you host here? What do you love about it? Guests feel that. Algorithms don’t.
If you’re a host, you’re not crazy, you are doing the work of a brand. If you’re a destination, you’re not wrong, there is a quality gap, and you’re tired of tiptoeing around it.
But no one wins if we stay on opposite sides of the story.
The best STRs are trying to build belonging. The best DMOs are trying to protect a sense of place. They’re trying to do the same thing. Just not together. Yet.
And if you’re us?
We’re working on it. We’re solving the “mystery host” problem. We’re designing a way to connect the dots without burning the whole thing down.
Wanna join my coven..errr...cohort? You know where to find me.
xo, Jenn
Originally published on LinkedIn, Sep 2025. This is its home now.
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