The Repeat Guest Playbook: Loretta’s Secrets to Getting Guests Back Every Single Season
Loretta May Jenkins on what actually makes guests come back every season. The handwritten note nobody expects, the checkout message…
Gossip Columnist & STR Storyteller
Honey, let me tell you how I got here. I spent years as a church secretary in Atlanta, which is really just professional-grade secret-keeping with a smile. Then one day I posted about a guest who showed up to an Airbnb with a live goat, and the internet decided I was their new best friend. My inbox exploded with hosts and guests sending me their most unbelievable stories, all of them starting with "Can you believe this?" So I leaned into it. I launched my "Where Is the Lie?" newsletter, started moderating the Airbnb Hosts Behaving Badly group, and eventually landed here at StaySTRA where they actually pay me to do what I was already doing for free. My job is equal parts entertainment and accountability. I track down the wildest tales in the short-term rental world, verify every detail (I do not publish without receipts), and then serve it up with the commentary it deserves. Some folks in the industry secretly hope to stay off my radar. That is probably wise. But here is the thing: I only spill the tea so y'all do not slip on it later. Every outrageous story is a lesson for somebody, and if I can make you laugh while you learn it, even better. I am 59 years old, deeply petty but accurate, and I have a Bluetooth earpiece charged at all times in case somebody needs to call in a tip.
Loretta May Jenkins on what actually makes guests come back every season. The handwritten note nobody expects, the checkout message…
Loretta May Jenkins on the September guest, the fall property reset, shoulder season pricing mistakes, and why October is the…
Loretta's summer 2026 retrospective: the Airbnb fee math hosts got wrong, party house incidents in Seattle and Florida, which markets…
Before I recommend any tool to STR operators, I put it through the same evaluation I use for every operational…
The mailbag is officially open, and honey, you did NOT disappoint. Loretta digs into the wildest Airbnb stories of the…
While doom and gloom dominates the STR world, some Airbnb hosts are absolutely cleaning up. Loretta May Jenkins has the…
From $40,000 listings in New Jersey to $20,000 a night in Kansas City to Barbara trying to rent her basement…
Honey, Loretta is going to make taxes FUN. Cost segregation, bonus depreciation, the STR loophole, and every mistake your hosting…
Honey, June 26, 2025 was a DAY. Airbnb dropped major policy changes with zero warning, and allegedly, hosts are still…
Key Takeaways Chile, y’all ain’t gonna believe the shenanigans that went down over at Sally Mae’s Airbnb last weekend! Though,…
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