The Airbnb Hosts Who Are THRIVING While Everyone Else Is Crying

Now honey, I don’t like to start trouble, but I am about to say something that is going to upset a whole lot of people in the STR Facebook groups I moderate, and I want you to know I mean it with love.

Some of y’all are out here absolutely CRUSHING it. And the rest of y’all are watching them do it and wondering why the world is so unfair.

Lord have mercy, where do I even begin.

It was a Tuesday when I got the call from my dear friend Patrice — she runs a little host meetup down in Savannah every third Saturday, bless her heart, and she called me up sounding absolutely defeated. “Loretta,” she said, “I have had three cancellations this month and my calendar looks like a Swiss cheese. Something has GOT to change.”

I told Patrice what I am about to tell all of you, which is: honey, the market didn’t break. The market SORTED. And if you are sitting there with a beige bedroom and a Walmart shower curtain wondering why the bookings aren’t coming, I need you to sit down because Loretta is about to give you some hard truths wrapped in sweet tea and Southern charm.

The Situation, As Loretta Understands It

Now I leave the number-crunching to the smart folks over at StaySTRA, but I will tell you what I have been HEARING — and honey, I hear things. The short-term rental market has gotten CROWDED. Like, your cousin Herb’s pickup truck at an all-you-can-eat buffet parking lot kind of crowded. There are listings everywhere, in every little suburb and cul-de-sac, and the average guest has options that would make their grandmama’s head spin.

My colleague Edna Stewart — the one who actually reads spreadsheets for fun, bless her — wrote a whole piece about the state of short-term rentals in 2026 that will tell you exactly what the data says. And there’s another one about whether the market is really oversaturated or just overhyped that is very informative if you are the type who likes actual facts.

I prefer gossip. But the gossip and the facts are telling the same story this time, and that story is: the beige are struggling and the BOLD are thriving.

The Shipping Container Above a Waterfall

Chile, y’all are NOT going to believe this one.

So there is a place called the Ellwood Box Hop in Rockbridge, Ohio, and I need you to picture this with me. Someone — and I want to shake their hand — took a SHIPPING CONTAINER. A regular old industrial shipping container, the kind that holds actual freight on actual cargo ships. And they suspended it. Above a waterfall. With a GLASS FLOOR.

You can look straight down through the floor at the water rushing underneath you while you eat your breakfast.

I swear on my mama’s fried chicken recipe, I am not making this up.

Now when I heard this, I called my book club friend Deborah, who has very conventional taste in vacation rentals (she favors hotels with turndown service and mints on the pillow, God love her), and even Deborah said “Well Loretta, I would absolutely book that.” And Deborah once called a place “too rustic” because the bathrobes were terry cloth instead of waffle-weave.

The Ellwood Box Hop is booked. Consistently. Repeatedly. By people who found it on the internet, showed their spouse, and said “we are GOING HERE.”

That is the power of being genuinely, gloriously, uncompromisingly weird.

The Oregon Treehouse That Lives in an Octagon

Up in Dallas, Oregon — yes, there is a Dallas, Oregon, and before you ask, I have no idea if it is anything like the Texas one, though I suspect the vibe is quite different — there is an octagonal treehouse with windows that look out in every direction into the forest.

Eight sides. All windows. Suspended in actual trees.

Now I have been to a few treehouses in my time. My cousin’s ex-husband Herb built what he called a “treehouse” that was really just a platform nailed to an oak with a camping chair on it, and he charged his nephews five dollars to use it, and I will say that was a different experience entirely.

This treehouse is not that. This treehouse has deck space and campfire amenities and the kind of Instagram opportunities that make people book twelve months in advance.

The host of this property did not accidentally become successful. They made CHOICES. Every single design choice was a choice about who their guest would be and what story that guest would tell when they got home. And the story their guests are telling is “I slept in a beautiful octagonal treehouse in the Oregon forest and I need to go back immediately.”

Where is the lie?

Meanwhile, In a Cave…

Honey, we are not done with the unique properties tour.

Over in Houston, Alabama — not Texas, Alabama, yes it exists, I had to look it up too — there is a vacation rental built INTO ACTUAL ROCK on Smith Lake. Not near the lake. Not with a lake view. Built into the rock itself, on the lake, like someone decided the mountain was just living space that hadn’t been realized yet.

People on the internet have called it one of the craziest and coolest Airbnbs in existence. I believe them.

Now I want you to think about the host of this property. I don’t know their name but I have constructed an entire personality for them in my head — let’s call her Donna. Donna looked at a rock face on a lake and saw a vacation rental. While the rest of us would have seen: a rock. Donna saw: a booking calendar so full you’d cry.

Donna is THRIVING.

The Canadian Treehouse With the Highland Cattle

Oh, this one is my favorite because of the cattle.

Up in Chilliwack, British Columbia — which is a real place and a name that makes me happy every single time I say it — there is a Nordic-inspired forest treehouse. It has a sleeping loft. It has a modern kitchen. It has an outdoor hot tub, because of course it does.

And it is surrounded by Highland cattle.

Not, like, cattle in a distant field that you might glimpse through the trees. HIGHLAND CATTLE. The fluffy ones with the long hair and the horns and the faces that look like they belong on a tea towel. Right there. Looking at you.

My friend Martha — the one who manages check-ins at my Vail condo — she called me from this property last fall and said, “Loretta, I am drinking wine in a hot tub and there is a cow looking at me through the trees and I have never felt more at peace in my entire life.”

Martha is not easily impressed. Martha has opinions about thread count. Martha gave this treehouse five stars and is planning to go back.

The host of that Canadian treehouse understood something that a lot of people have missed: people do not just want to rent a space. They want a STORY to tell at their next dinner party.

The Secret Weapon: Shameless Self-Promotion

Now here is where it gets really interesting, because it is not JUST about having a unique property. There is another ingredient, and it is the part that makes a lot of introverted property owners deeply uncomfortable.

You have to TELL PEOPLE ABOUT IT.

I moderate the “Airbnb Hosts Behaving Badly” Facebook group — don’t ask, it’s a whole thing — and I also follow a lot of host accounts on the socials, and let me tell you: the hosts who are winning right now are not shy. They are posting videos of their properties. They are walking through every room with a camera. They are showing the waterfall under the glass floor. They are posting the cow looking through the treehouse window.

And people are watching. Honey, people are WATCHING.

Travel videos have seen absolutely explosive growth on the social platforms, and when someone sees your vacation rental and goes “I need to be HERE,” they do not close the app and forget about it. They screenshot it. They send it to their partner. They book it.

The Colorado property that became one of the most-loved Airbnb listings on social media recently was, I am told, quite simple inside. What made it go viral was ONE unusual feature — a roll-out bed situation that was genuinely unexpected — and a host who was not afraid to show it off.

One unusual thing. Shown proudly. That is the formula.

The Hosts Who Are Using Every Advantage

Now I have been known to wave my hand at technology and say “I leave that to the young folks,” but I will tell you that even Loretta has noticed that the hosts who are doing the best right now are using their tools.

There’s a whole piece on this site about how AI is running the operations of the majority of STR businesses now that my colleague wrote, and while I don’t fully understand all the particulars, I understand the gist: the hosts who are not using smart tools to price their properties and manage their calendars are leaving money on the table while other people scoop it up.

The market rewards the prepared. Always has, always will.

What Patrice Is Doing About It

I’ll tell you how my conversation with Patrice ended, because it has a happy ending and I do love a happy ending.

After I talked to her for about forty minutes — which I will admit is unusually short for one of our conversations — Patrice got quiet and then said, “Loretta, my guest room has a normal bed and a reading chair and a picture of a lighthouse.”

I said, “Patrice, is the lighthouse picture nice?”

She said, “It’s from HomeGoods.”

Chile.

Now Patrice is a resourceful woman. Within two weeks she had repainted that room a deep, dramatic teal. She had found a local artist to paint a REAL piece of art for the wall — paid her a reasonable amount, supporting local talent, love to see it. She added a rainfall shower head to the bathroom and a robe so fluffy it could double as a small dog. She took photos herself, walking through the room with her phone, talking about every detail like she was showing a friend.

She posted it. She promoted it. She waited.

Her calendar filled up.

Allegedly. But I was on the phone with her when she was screaming about it, so I would say: also absolutely.

The Lesson, Such As It Is

Here is what I have learned from watching this whole drama play out in real time, from my perch at the Piggly Wiggly checkout line and my seat at book club and my Facebook group and my very extensive network of people who tell me things:

The STR market is not dying. It is SORTING.

The generic is getting crushed. The remarkable is getting rewarded. The host who built something beautiful and strange and then had the nerve to tell the world about it — that host is looking at a full calendar and a very satisfying bank statement.

The host who bought a condo, put a bed in it, and waited for bookings to roll in — that host is calling me on a Tuesday sounding sad.

Be Donna. Be the person who saw the rock face and saw a rental. Be the treehouse host. Be the woman who put Highland cattle next to a hot tub and called it a feature.

The guests are out there, honey. They are ready to book something that will make them gasp. Give them something to gasp about.

Now honey, I do my best to keep the tea fresh and accurate, but things change and lord knows I am only human. Always double-check the details before making any big moves in the STR world.

And if this whole saga has got you curious about what your market actually looks like right now, the folks over at StaySTRA can show you the real numbers. I will stick to the stories.

Allegedly. But also absolutely.

Don’t Miss the Next Story

Honey, if you enjoyed this, you are going to love what comes next. Join the StaySTRA Insider newsletter and I will make sure you never miss the good stuff.