HOW TO CRAFT A MESSAGE THAT STICKS WITH EVERY GUEST
When I arrived in Los Angeles at 20 years old, I didn’t know that my first career in film advertising would end up shaping how I see travel.
I was writing and producing movie trailers—two-minute stories designed to make you feel something fast. Those trailers had to pull you in, give you goosebumps, and convince you, within seconds, that this movie was worth the watch.
Now, years later, I find myself doing something surprisingly similar—only instead of movie trailers, I help hosts tell the story of their stays.
At its core, short-term rental marketing is storytelling.
When done right, it’s emotional architecture. And , it doesn’t just sell an overnight stay—it creates belonging, memory, and connection that last long after checkout.
Short-term rental marketing is storytelling. When done right, it’s emotional architecture.
GIVING YOUR GUEST A STORY-DRIVEN EXPERIENCE
6 ESSENTIALS THAT WILL CARRY THE STORY OF YOUR STAY
Like the word “experience,” the term “story” has become a buzz word in the travel industry, especially in short term rentals. But actually delivering a story experience in a cohesive, compelling way takes strategy and attention to detail.
Olive Jar client property: The Sideline Club (Photo Credit: Kristina Holman)
Must-Have #1: Give Them More Than a Vibe—Send a Message
Do you remember all those “Live, Laugh, Love” signs from the nineties? Somewhere along the way, they evolved into neon signs like: “Good Vibes Only,” “Stay Awhile,” or “Rosé All Day.” Hosts put these lines on display because they’re trying to set a mood, to give guests a sense of energy. And there’s nothing wrong with that instinct.
But what’s often missing is the depth behind the vibe.
Those signs are shorthand for something hosts genuinely want to communicate: “This space is about joy,” “This stay is about slowing down,” “This place is for you.” The trouble is, when the message becomes too surface-level, guests can sense its just decoration. The whole picture experience lacks real emotion.
Branding, at its best, is vibe creation with meaning.
Meaning is found in touch points that expand the basic, ordinary and cookie cutter formulas like:
Host Correspondence: Automated information vs. Active listening responses that reflect back your traveler’s words
Design Scaffolding: A basic bookshelf of books vs. Implementing decor detail that peak curiosity and pair with those titles
Interactive Amenities with Feeling: A pickleball court vs. a pickleball court with a “humble brag” scoreboard that boosts confidence & camaraderie
At The Olive Jar, we like to ask: What will your guests say about your stay?
Cue Must-Have #2.
Brand Refresh inspiration for Olive Jar client: Mountain Mama Ranch
Must-Have #2: Clarity Creates Connection & Trust
Branding, at its essence, is about creating clarity. The story of your stay should be so distinct that your guests can walk out the door and tell someone else about it in like TWO sentences—and the person on the other side gets it.
That clarity doesn’t happen by accident. It happens by design.
When we work with hosts, our first step is always a Brand Story Guide.
It’s not just a logo or a color palette—it’s the narrative spine of the entire experience.
For one of our clients with a 200-acre ranch, we asked the question, What IF Jane Austen met John Denver on a modern day ranch?
We uncover what you want your guests to feel, what you want them to remember, and how you want them to describe you when you’re not in the room.
Because the truth is, people don’t talk about five-star amenities. They talk about how they felt.
That clarity builds connection—between your design choices, your messaging, your media, and your traveler’s story. AND, it builds trust in YOU. Cohesively communicates that you know what you’re doing. You’re a professional.
When every detail points to the same emotional through-line, your guests carry that clarity home with them.
Must-Have #3: Design Moments That Feel Like Story Beats
A story is made of moments that feel personal. So is a stay.
When we build branding guides, we think like filmmakers: what are the “beats” of your guest’s story? How will they feel the urgency to get there? And once they do, where will they feel wonder, intimacy, nostalgia, or joy that strikes a chord?
That same 200-acre ranch I mentioned earlier sleeps 18 guests and sits before a stunning view of the Blue Ridge Mountains. Spring boarding from that story spine about Jane Austen & John Denver, we designed a guest experience around the feeling of wild whimsy.
On our mood board, we included a tree swing by the pond with golden light peaking through the leaves. Even if our host doesn’t end up building the swing, the feeling of it guides every design and interactive detail choice moving forward.
Emotion lives in small moments.
Case in point:
This property now offers wooden wagons (later they could brand them, too) for guests to fill with a picnic spread and bring down to that pond. Suddenly, a large group experience becomes an intimate moment. Can you see it?
An intimate moment makes a sprawling property feel personal.
Your job as host is to usher your traveler into THOSE moments.
Brand Refresh inspiration for Olive Jar client: Mountain Mama Ranch
Olive Jar client property: Camp Kindred (Photo Credit: The Olive Jar & Anchor Pictures)
Must-Have #4: Remember Your Traveler is the Hero of Your Story
A few blog posts ago, we talked about the “Transformation Economy”—this idea that people don’t just want to buy experiences anymore; they want to be changed by them.
We are, by nature, story beings. In every film, the hero, aka “the protagonist,” is the character who changes the most. They start in one emotional state, face a dilemma, encounter challenges, and emerge transformed.
Your traveler is that hero.
When they book your stay, they’re seeking something—rest, adventure, reconnection, healing. They arrive with an inner longing. Your space is the setting where transformation happens.
Let’s break it down:
Act I: Your Traveler Has a Dilemma
The setup. You meet your future guest (aka Hero), and they get their first impression of you. This is your establishing shot, where your brand essence is crystal clear and your marketing SO compelling that your story is worth the stay.
Act II: Your Traveler Becomes Your Guest
Your Hero has arrived! The heart of the story. Guests settle in, explore, relax, reconnect. These are your “fun and games” scenes — the emotional high points, the laughter, the small surprises that anchor memory.
Act III: Your Guest Transforms Into Your Fan
By the time they’re checking out, they’re sold.
But checkout isn’t the end of the story — it’s your closing scene. What lasting emotion do you want to leave them with? Nostalgia? Inspiration? Gratitude?
The story continues in how they talk about you — the sequel they write in their own words.
Olive Jar client property: Camp Kindred (Photo Credit: The Olive Jar & Anchor Pictures)
Must-Have #5: Don’t Skimp on Details—They’re Driving Your Reviews
Everyone wants five-star reviews. But the stars themselves don’t tell the full story—the details in a review do.
Because guests can’t invent details that weren’t there.
If you want guests to write vivid, heartfelt reviews, you have to give them vivid, heartfelt moments.
Guests call out the details you’ve intentionally designed.
We were handed a property that gets high precipitation throughout the year. So, the odds for clear skies are sometimes not in the traveler’s favor. BUT, we turned that pain point into pleasure with a sensory-rich “Rainy Day Guide.” A few prompts include:
SPIN OFF: Get your vinyl party on. Winner of best performance rules the turntable ‘til dusk.
RAINY DAY LIBRARY: Peek our hidden collection, specially curated for quiet moments with a symphony of sounds outside your window
TAKE A DRIVE: Drive the winding roads of Deep Creek State Park with windows rolled down. Let your fingers dance with the falling rain.
When you curate experiences with that level of intentional hospitality, guests don’t just notice, they start to seek and find it in all on their own. Rain or shine.
That self-discovery leads them to write more detailed stories. They share photo snaps. They spread your story for you.
And yes, there IS an ROI that shows up in your numbers.
after investing in Olive Jar experiential marketing services, Our clients usually see 30–50% increases in ADR and annual revenue
This client raiseD her ADR BY 300%.
Yes, you read that right. The bookings were instant, no discounts asked.
But beyond that, our clients see something even more rare: organic buzz…
That’s kind of attention you can’t buy, only inspire.
That’s the word-on-the-street you can’t fabricate. It’s earned through care.
And, that’s what happens when your guests stop being spectators of your story and start living through it.
Must-Have #6: Lead with Generosity
Storytelling, at its heart, is an act of generosity.
For over a decade I’ve been quoting one soulful truth by Seth Godin:
“Fans, true fans, are hard to find and precious.
What they demand, though, is generosity and bravery.”
In hospitality, generosity isn’t about discounts—it’s about giving more than expected:
the surprise scavenger hunt or hidden playlist
the mocktail recipe books at the bar
a complimentary late-check out before the guest even asks
These are acts of generosity that create a dopamine reward moment.
When people are already in a positive emotional state and receive something unexpected, their brain releases dopamine, reinforcing attachment. In other words: that little act of generosity literally bonds your guest to your brand.
And the best part? Generosity is generative. It creates momentum. Guests talk about it, return for it, and build community around it.
“Surprise and delight” isn’t an afterthought. It’s strategy with magic.
But simply, it’s a story moment that sticks long after your guests leave.
Ready to make some movie magic?
The Olive Jar has built a Guest Journey Map template to help hosts visualize this full story arc—identifying what sparks a connection, where emotion peaks, and where the story can go deeper. Because the more intentionally you script the emotional flow of your stay, the more unforgettable it becomes.
If you’re a host who wants exclusive access to that Guest Journey Map, start by discovering a little bit about yourself.
JOURNEY WITH US
If this is your first time meeting me, well hello! I’m Dawn, Founder and Creative Director of The Olive Jar. Our mission has always been simple and human: to create *Getaways to Reconnect.*
We believe travel is one of the last sacred spaces for belonging — a chance for people to rediscover themselves and each other. But in a world that often feels disconnected, it takes imagination and strategy to make that happen.
That’s why we use experiential marketing frameworks to build a loyal following for every visionary host we serve. We help hosts turn their rentals into sensory, story-rich experiences — places where travelers don’t just stay, but transform.
Because when you design a stay with story in mind, you’re not just marketing a space — you’re crafting meaning.
And meaning is what keeps your guests coming back, season after season.
P.S. If you liked this post, you’ll really dig an entire PODCAST conversation around this stuff.
Listen to my Cabin Culture podcast interview, hosted byCozy Rock Cabin’s Janice Smith, where we expand on the essentials I’ve covered here today.