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  3. Loretta’s Mailbag: The Wildest Airbnb Stories Y’all Sent Me This Month

Loretta’s Mailbag: The Wildest Airbnb Stories Y’all Sent Me This Month

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Loretta May Jenkins
February 26, 2026 20 min read
A vintage mailbox overflowing with colorful letters on a Southern porch, with sweet tea and a brooch nearby

Key Takeaways

  • Well, y’all, I have been holding out on you.
  • This is not what I expected from a cabin in the woods.
  • And you, the actual property owner, had no idea any of it was happening because the middle-man had quietly folded up shop and departed.
  • The “gathering” man in Nashville?

Well, y’all, I have been holding out on you.

Two months ago, right here on this very website, I put out a little invitation. I said, honey, if you have got a wild STR story burning a hole in your heart, you send it to Loretta. I have got a sweet tea, I have got a porch, and I have got absolutely nowhere to be.

Chile, the response nearly knocked me sideways.

My inbox looked like the lost and found bin at a theme park. Hosts. Guests. Property managers. One person who described themselves as “a concerned neighbor who has seen things.” The stories came rolling in from all corners of this great nation, and I have spent the better part of three weeks sorting through them, cackling to myself, forwarding the very best ones to my friend Martha, and then cackling some more when she called me back speechless.

So. Without further ado. Welcome to the inaugural installment of Loretta’s Mailbag, a recurring monthly feature where I open up the floodgates and let the wildest Airbnb stories y’all sent me loose upon the world.

Pour yourself something cold. This is going to take a minute.


Letter #1: “The Sand People”

“Loretta, I own a beach cottage in the Outer Banks. Three-bedroom, sleeps eight, been doing this for four years without a single serious incident. Then came what I now refer to simply as The Sand People. A family of six booked for a week in peak season. When I did the checkout walkthrough, I found approximately eight hundred pounds of sand inside my house. Not tracked in on feet. Transported. There were buckets, Loretta. Empty buckets. They had been using buckets to bring sand in from the beach and pile it in the corner of the living room. There was a handmade sign that said SANDCASTLE ZONE. My vacuum has not been the same since. Signed, Still Finding Sand in February, Sheila R., North Carolina”

Lord have mercy, Sheila.

I read this letter three times. I called my cousin Darla to read it to her. Darla, who has the emotional range of a parking meter, laughed until she wheezed. I almost spilled my sweet tea on my good brooch, the one with the little enamel hummingbird.

Now I want to be fair. I want to give The Sand People the benefit of every possible doubt. Maybe they had a child who was deeply passionate about architecture. Maybe someone had a dream. Maybe there was a miscommunication about what “beachfront property” means and they thought they needed to bring the beach INSIDE with them.

But Sheila, honey. There was a sign. A handmade sign. They planned this. They packed buckets. They made multiple trips. This was an organized sand-relocation operation, and somebody in that family was the ringleader.

I hope you charged for every grain.

And for the love of all that is holy, take a peek at how to screen your guests properly before next season, because no background check in the world is going to catch “chronic indoor sand accumulator” as a red flag, but at least you can ask some pointed questions in your pre-booking message.


Letter #2: “The Party Heard Round the Neighborhood”

“Hi Loretta, big fan. I have a condo in Nashville and I installed a Minut noise monitor last spring after a situation I will not detail here but which involved a fog machine and a citation from the fire marshal. Fast forward to October. I get a Minut alert at 11:42pm on a Friday. Decibels: 94. That is louder than a lawnmower. I pull up my Ring doorbell camera and see seventeen people going into my unit. The booking was for two guests. I called the guest immediately. He told me, and I am quoting verbatim: ‘It is not a party it is a gathering.’ I told him to gather everyone out of my property within thirty minutes or I would be calling the non-emergency police line and Airbnb simultaneously. He said, quote, ‘You can’t prove anything.’ Loretta, I had seventeen people on camera, noise readings logged to the cloud, and receipts. They were gone in twenty-two minutes. Signed, Victorious, Bartholomew T., Nashville”

Bartholomew. BARTHOLOMEW. I could hug you through this screen.

“You can’t prove anything.”

Baby, this is 2026. We have CAMERAS. We have decibel monitors that log to the cloud. We have smart locks that tell us exactly when doors open and close. We have video doorbells and motion sensors and apps on our phones that ding at us from three states away. The era of plausible deniability in vacation rentals ended approximately seven years ago, and yet here is this young man, fog of war rolling in, seventeen of his closest friends crammed into a two-guest condo, telling a property owner “you can’t prove anything.”

Bless his heart. Genuinely.

The receipts, y’all! The receipts were TIMESTAMPED and CLOUD BACKED UP.

And Bartholomew, you absolute legend, they were gone in twenty-two minutes. That is faster than a pizza delivery. Those seventeen people grabbed their solo cups and their dignity (such as remained) and scattered into the Nashville night.

The fog machine incident from the spring is what really gets me though. I am going to need that story for next month’s mailbag. Please write back.


Letter #3: “The Revenge Review That Went Sideways (For the Guest)”

“Loretta, I need to tell you about a review I received last summer that nearly sent me to an early grave. I run a cabin in the Smokies. Lovely place, five stars almost always. Then a guest checked out and left me this review: ‘One star. The cabin smelled like pine. There were trees everywhere outside. I could hear owls at night. This is not what I expected from a cabin in the woods. Host is unresponsive to concerns.’ Loretta, I was never made aware of any concerns. I checked my messages. Not a single message from this guest during their stay. I had no idea what she wanted. I responded publicly. I said: ‘Thank you for your review. Our cabin is indeed located in the woods, which does contain trees, wildlife, and the naturally occurring scent of pine. We wish you well in your future search for a forest-free forest experience.’ The response got 847 upvotes on the Airbnb host Facebook group. Signed, At Peace With Nature, Cordelia B., Tennessee”

“A forest-free forest experience.”

I need everyone to stop what they are doing and appreciate Cordelia B. from Tennessee for one full moment.

This woman was subjected to a one-star review because her cabin in the woods had TREES in it and OWLS outside it and SMELLED LIKE PINE, which is what pine trees smell like, which is a thing that has been true since before recorded history, and she responded with the poise and precision of a seasoned diplomat.

“A forest-free forest experience.”

That is a whole masterclass in host communication right there. She did not get defensive. She did not explain herself. She did not argue. She simply reflected the absurdity of the situation back to the reviewer with such gentle, devastating accuracy that the entire hosting community gave her a standing ovation.

847 upvotes, Cordelia. You earned every single one.

Now listen. I do want to say something slightly serious here, because I have seen this kind of situation go very wrong when hosts fire back with anger instead of wit. The moment you type something mean or accusatory in a public review response, you have handed that guest a weapon. Cordelia understood something fundamental: the best revenge is making the reviewer look ridiculous without breaking a sweat. She let the review speak for itself, and then she added one perfect sentence that turned the whole thing into a comedy sketch.

That is an art form, y’all.


Letter #4: “Mister Gerald”

“Dear Loretta, I want to share a different kind of story. I host a small cottage in coastal Maine. Nine years ago, a retired school principal named Gerald booked for a week in September. He was the quietest, most respectful guest I have ever had. He left a handwritten thank you note and a box of chocolates on the kitchen table. He booked again the following September. And the September after that. Every year without fail, like the tides, Gerald comes back to his cottage. I know how he takes his coffee now. I leave a pot of his favorite blend waiting when he arrives. His wife passed three years ago, and the September after that he sat on the porch and cried for a while, and I brought him a piece of pie and we talked about her for an hour. Gerald has been here nine times now. He is turning seventy-five this year. I have already started planning a little surprise for him. This job gives me that. Signed, Grateful for Gerald, Patricia H., Maine”

Okay. I need a moment.

I am not crying. I am not. I am just…my eyes are leaking a little bit in sympathy for Patricia’s beautiful letter and it is absolutely the pollen in the air right now.

Y’all, this is why I do what I do. This is why I talk about this industry the way I do. Because for all the sand buckets and unauthorized gatherings and one-star reviews because of owls, there is also this. There is a retired schoolteacher named Gerald who found a place that feels like home when home is lonelier than it used to be. There is a host named Patricia who noticed, who cared, who set out a pot of coffee and a piece of pie at exactly the right moment.

There is something that happened on that porch in Maine three years ago, a woman bringing a grieving old man a slice of pie and sitting with him for an hour, that no platform rating system will ever fully capture. No five-star review can hold it. No algorithm can measure it.

But it happened. And it matters. And Mister Gerald comes back every September because it matters.

I hope his seventy-fifth birthday is absolutely wonderful, Patricia. Please write and tell me how it goes.


Letter #5: “The Property Manager Who Vanished Into the Ether”

“Loretta, I hired a property management company for my mountain condo two years ago. Twenty-eight percent fee. They handled everything, or so I was told. Six months in, I drove up to check on things and found my lockbox was empty, my spare key was missing, the last cleaning log showed a date four months prior, and there was a note from a guest tucked under the door mat that said ‘I stayed here last weekend, the hot tub was broken and smelled terrible, I have been trying to reach someone for a refund for three weeks.’ I had received zero communication from my PM about any of this. When I called them, the number had been disconnected. Their website was still up. Their Facebook page still showed glowing testimonials from 2022. They had evaporated, Loretta. With my twenty-eight percent. Signed, Still Furious in February, Rhonda K., Colorado”

Rhonda, honey, I am so sorry.

Lord have mercy, this is a story I hear more than I would like to. Property managers who walk off with the fees and leave the property to fend for itself. And twenty-eight percent is not a small number, y’all. On a busy mountain property, that adds up to real money disappearing into thin air along with whoever was supposed to be managing the situation.

The hot tub, Rhonda. THE HOT TUB. That poor guest was sitting in a broken, funky hot tub and then could not get a refund for three weeks because the management company was in the process of evaporating. And you, the actual property owner, had no idea any of it was happening because the middle-man had quietly folded up shop and departed.

This is not a rare story, and I want every single person reading this to go read what you need to know about property management fees and what you are actually paying for, because the fee percentage is only the beginning of the conversation. Who is answering the phone at 2am? Who is checking on the property? What does the contract say about accountability? What are the red flags that your PM has gone rogue?

Get your documentation in order. Know what you are paying for. And maybe drive by every so often just to confirm the hot tub is not smelling up the neighborhood.

Rhonda, I hope you have since found someone trustworthy. If not, write back and we will talk.


Letter #6: “Two Families, One Condo, Zero Good Outcomes”

“Loretta, I need to confess something. I am the host who double-booked. I had a family of four from Ohio booked for the Fourth of July weekend at my beach condo. I also, somehow, through a channel syncing error that I still do not fully understand, had a family of five from Georgia booked for the exact same weekend. I did not realize this until the Ohio family called me from the parking lot on the afternoon of July third to say they could not get into the unit. The Georgia family was already inside. They had been there for two hours. I would like to say I handled this with grace. Loretta, I did not. I hyperventilated into a paper bag, called my husband three times, and ultimately had to comp the Ohio family three nights at a nearby hotel, refund them fully, and give them a future stay credit. The Georgia family stayed but left three stars because they, quote, felt the energy was weird. Loretta, the energy was weird because I had a meltdown on the phone in front of them while their children watched television. Signed, Humbled and Now Using a Channel Manager, Douglas F., Florida”

Douglas. Oh, Douglas, honey.

“The energy was weird.”

It was! It absolutely was! The energy was two families in the same condo, a hyperventilating host on the phone, and a Fourth of July weekend that was not going the way anyone had planned. The energy was EXTREMELY weird and three stars is frankly generous under the circumstances.

Now I am not going to pile on Douglas because Douglas has clearly suffered enough. He has confessed his sins publicly. He has paid his penance in hotel bills and future stay credits and a three-star review referencing the ambient energy of his vacation property. He has learned. He now uses a channel manager. He has grown as a person and as a host.

But let me tell you something, because the Fourth of July weekend double-booking is practically a rite of passage in this industry and it should not be. If you are listing on multiple platforms, you need a channel manager that syncs your calendar in real time, and you need to test it before peak season, not discover it is broken when an Ohio family is standing in a parking lot in the July heat calling you from a number you do not recognize.

Douglas, we salute your honesty. And your paper bag. And the Georgia family for their mercy.


Letter #7: “The Unreasonable Request Hall of Fame”

“Loretta, I have been hosting for six years and I keep a list. The list is called ‘Things Guests Have Actually Said to Me With Their Whole Chests.’ I would like to share a few entries. Entry one: A guest requested a refund because there was a spider outside on the deck. Entry two: A guest complained that the sunrise was ‘too early and too bright’ and asked if I could adjust it. Entry three: A guest left a two-star review stating, and I quote, ‘the house smelled like someone had been cooking in it.’ Entry four: A guest called at midnight to report that they could hear frogs and asked me to ‘do something about the frogs.’ Entry five: A guest asked me, three weeks before their arrival, whether I could ‘arrange for good weather.’ These are real. I have kept this list as a coping mechanism. Signed, It Keeps Me Sane, Beverly Ann W., South Carolina”

Beverly Ann. BEVERLY ANN. You have been carrying the weight of this list for six years and I need you to know that sharing it with the world is a public service.

“The house smelled like someone had been cooking in it.”

Well. Yes. It is a kitchen. A kitchen is a room specifically designed for the purpose of cooking things in it. The smell you are detecting is the lingering evidence of hot meals prepared by actual humans using the equipment provided. This is a feature, not a bug.

And the frogs. The FROGS. I want to paint a picture here. Beverly Ann, somewhere in South Carolina, at midnight, is being asked to resolve a frog situation. What does one do? Does one go outside with a flashlight and have a firm conversation with the local amphibian community? Does one post a notice in the wetlands? Does one explain to the frogs that there has been a complaint?

I swear on my mama’s fried chicken recipe, if I ever get a call about frogs I am going to tell the guest that the frogs are complimentary local wildlife and if they would like frog-free accommodations I will happily send them the link to a hotel in downtown wherever they are.

Beverly Ann, your coping mechanism is excellent. Please keep the list. I want to see all future entries. This mailbag will always be open to you.


Loretta’s Takeaways (Because She Cannot Help Herself)

Now look. I told myself this was just going to be a fun little roundup and I was not going to turn it into a lesson. And then I turned it into a lesson because that is who I am as a person and I have made peace with it.

Here is what these seven letters tell me about this industry in 2026:

  1. The guests who write the best villain stories are almost never actually villains. The Sand People? They probably thought they were being creative. The “gathering” man in Nashville? He is twenty-three and did not think anyone was watching. They are not evil. They are just people who needed more guardrails and clearer house rules.
  2. Technology is a host’s best friend. Bartholomew’s Minut monitor saved his condo and his sanity. Douglas’s pain could have been entirely avoided with a channel manager. Tools exist. Use the tools.
  3. The public review response is the host’s most underused superpower. Cordelia understood this. It is not about defending yourself. It is about showing future guests who you are.
  4. Not all property managers are created equal. Rhonda’s story is a cautionary tale I hear too often. Do your homework. Know your contract. Drive by occasionally.
  5. Gerald exists. In every market, in every season, there is a Mister Gerald out there looking for a place that feels like home. Build the kind of place he keeps coming back to.

Now honey, we do our best to keep the tea fresh and accurate, but these are composite stories inspired by real experiences shared in host communities, and Loretta always says to double-check the details before making any big moves. The stories are real in spirit even when the names are made up to protect the innocent (and the guilty).

And if this whole wild mess has got you curious about what the STR market actually looks like in your part of the world, the smart folks at StaySTRA have the real numbers. I will stick to the stories.

Allegedly. But also absolutely.

Where is the lie?


Send Me Your Stories for Next Month’s Mailbag

Y’all, the mailbag is staying open. If you have got a story burning a hole in your heart, a guest situation that defies explanation, a host clap-back for the ages, a property manager who ghosted you, or a Mister Gerald of your very own, I want to hear it. Write to me at the address below, keep it real, and sign off any way you like. I will protect the innocent and roast the guilty with love and excellent grammar.

Next month’s mailbag drops March 26. Send your stories, darlings. Loretta is listening.

Frequently Asked Questions

Who is Loretta on the StaySTRA blog?

Loretta is a beloved voice on the StaySTRA blog who shares stories, advice, and commentary about the short-term rental industry with her signature Southern charm. Her posts blend humor with practical hosting insights, making complex industry topics approachable and entertaining. She has become a favorite among the StaySTRA community for her candid storytelling.

What topics does Loretta cover on StaySTRA?

Loretta writes about everything from wild guest stories and hosting mishaps to tax strategies and industry news. She is known for her reader mailbag columns, humorous takes on hosting challenges, and ability to make even dry regulatory topics engaging. Her Southern style brings warmth and personality to the short-term rental conversation.

Do I need a permit to operate a short-term rental?

Most cities and counties require some form of permit, license, or registration to operate a short-term rental legally. Requirements vary significantly by jurisdiction, so check your local government website or contact your city clerk before listing your property. Operating without required permits can result in fines ranging from several hundred to several thousand dollars per violation.

How do I find the STR regulations for my area?

Start by searching your city or county government website for short-term rental or vacation rental ordinances. Many municipalities have a dedicated STR registration page with application forms and requirements. You can also contact your local planning department directly or consult with a real estate attorney who practices in your area.

What safety features does my Airbnb need?

At minimum, every STR needs working smoke detectors in each bedroom and hallway, a carbon monoxide detector on each floor, a fire extinguisher in the kitchen, and a clearly posted emergency exit plan. Many jurisdictions also require exterior lighting, handrails on all stairs, and pool fencing if applicable. Airbnb requires hosts to confirm safety equipment in their listing.

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Loretta May Jenkins

Loretta May Jenkins

Gossip Columnist & STR Storyteller

Former church secretary turned internet-famous STR storyteller. I write the stories hosts whisper about and guests hope nobody finds out. If it happened in a short-term rental, I probably already know.

Writes about: Gossip Hot Topics Airbnb Stories Editorial Uncategorized
15 articles · Writing since Jul 2023
Previous Article Building Your Direct Booking Channel: The Data Behind Reducing OTA Dependence Next Article Nashville Short-Term Rental Laws: Permits, Zones, and What Hosts Need to Know in 2026

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