Jay William
Founder | Villa Marketers
25 Years in Hospitality, Direct Bookings, and Vacation Rental Marketing
Direct Bookings • SEO • AI Tools • Branding • Advertising • Owner Acquisition • Growth Systems
- Last Updated
- 2026
- Reading Time
- 8 min read
- Reviewed for Accuracy
- 2026
On Airbnb, Booking.com, and Vrbo, most holiday rental listings sing the same tune — same phrasing, same photos, same “cosy retreat” copy. Owners up against bigger players feel like small fish in a vast ocean, but size isn’t what makes waves — distinction is. Good advertising isn’t about shouting louder; it’s about sounding like no one else. Here are the six tips that make that happen.
1. Sell the experience, not the property
Your guest isn’t buying a bedroom count. They’re buying a dream weekend, a family reunion, a golf trip, an anniversary they’ll still talk about years from now. Advertise the memory waiting to be made, in vivid specific language, and let the property be the backdrop the story happens against.
People don’t book bedrooms. They book the weekend they can already picture themselves in.
2. Target the right guest — go narrow, not broad
Every rental has a natural guest. Narrow-and-deep converts better than broad-and-shallow, and it stretches every pound of ad spend. A family property should paint the barbecue and the nearby park, not “sleeps eight.” A golf-adjacent cottage should show the morning light on the greens and the quiet house after eighteen holes.
Resonate completely with someone, not weakly with everyone. One ad that speaks fluently to a specific guest will out-book a dozen generic ones every time.
3. Advertise with a strategy, not on impulse
“Get more bookings” is a wish, not a plan. Before you spend anything, answer:
- What is the rate structure across the year?
- How many bookings do you need to break even?
- What is the plan for low-season visibility?
- Which platforms give you reach and manageable competition?
- Are there niche or interest-based listing sites worth being on?
- How do the ads feed your own site and brand, not just the platform?
As Franklin put it: if you fail to plan, you plan to fail. Advertising without answers to those six is just a way to burn budget faster.
4. Dare to be distinctive — be the purple cow
This is the key one. Blending in is the fastest way to be overlooked. The goal isn’t to be different for its own sake — it’s to be the only one like you, so you compete on being unforgettable, not on price.
That might be a headline with genuine humour or intrigue. A photo set that tells a story rather than a walk-through. A short video tour that shows what an evening there actually feels like. One signature detail no other listing has.
Every distinctive touch should point back to the experience the guest is buying. Seth Godin called this the purple cow. In a field of ordinary cows, be the one people stop to photograph.
Compete on being unforgettable, not on price. The ordinary cow doesn’t get photographed.
5. Fill your off-season with counter-seasonal niches
The off-season isn’t dead demand — it’s a different audience most owners never bother to advertise to. Identify travellers whose peak demand lands squarely in your slow months, and put your advertising in front of that specific niche. Birders, golfers, surfers, divers, anglers, hunters, and wine-tasting and wine-country travellers all move by season and species. Festival-goers, event attendees, and convention or business travellers move by calendar.
A property near wine country can fill the post-summer lull because harvest and crush season — roughly September to October in many regions — is exactly when wine travellers are actively planning their trips. Their peak is your trough.
Why it works: these guests aren’t shopping the same weekends everyone else is. You compete for attention when your calendar is soft and your rates are under less pressure — and you’re often the only nearby listing that even speaks their language.
How to do it: build long-tail content and listings around the niche and its season — “<activity> near <place>” — and target that specific audience instead of the generic “vacation rental” crowd. It’s the purple-cow thesis applied to the calendar: be the only listing in your area that a snook angler, a shoulder-season golfer, a wine-country weekender, or a convention attendee recognises as built for them.
Your off-season isn’t empty. It’s just full of people no one else is advertising to.
6. Lead with a clear call to action
An ad without a next step trails off. Make the CTA unmistakable and easy: Book Now, Check Availability, Message the Host. A lovely description that leaves the reader unsure what to do is a booking handed to someone else.
The guest should never have to work out what you want them to do next.
7. Point your ads back to your own channel
Advertising that only feeds the big platforms builds their business, not yours. Whenever you can, route attention toward your own website and direct-booking channel — where you own the guest relationship and the margin, and aren’t at the mercy of platform fees or ranking changes.
Airbnb, Booking.com, and Vrbo are excellent to be found on. The real goal is to turn that attention into bookings you control. That’s the difference between renting your audience and owning it — the same principle we lean into when choosing a property worth buying in the first place.
The takeaway
Great holiday rental advertising isn’t louder — it’s sharper and braver. Sell the experience. Speak to one guest. Plan with real goals. Refuse to blend in. Make the next step obvious. And drive it all toward a channel you own — starting with how the listing itself is written and what happens after the first stay.
- Ad leads with the experience, not the bedroom count
- One specific guest in mind (family, golf trip, remote worker, luxury)
- Rate plan and breakeven booking count you can name
- Low-season visibility plan you can point to
- One genuine point of distinction — hook, photo story, or video
- Unmistakable next step (Book / Check Availability / Message)
- Every ad routes attention toward a channel you own
If you want a hand sharpening your advertising — or building the site and brand it should point to — that’s what we do.
FAQ
How do I make my holiday rental ad stand out?
Lead with the experience rather than property specs, speak to one specific guest instead of everyone, and add a genuine point of distinction — a signature feature, a story-driven photo set, or a video tour. Be the only listing like yours so you compete on being memorable, not on price.
What should a holiday rental advertising strategy include?
Clear goals plus answers to practical questions: rate structure across the year, breakeven booking count, low-season visibility, which platforms balance reach and competition, niche listing sites, and how your ads feed your own website and brand.
Should I advertise on Airbnb and Vrbo or on my own website?
Both, with intent. The big platforms are excellent for being discovered; your own website and direct-booking channel are where you keep the margin and own the guest relationship. Build awareness on the platforms, then point that attention toward a channel you control.
Do I need different ads for different guests?
Yes. A family-focused ad and a golf-trip ad for the same property should read very differently. Tailoring the message to a specific guest's dream converts far better than one generic ad for everyone.
How do I get off-season or low-season bookings?
Target audiences whose peak demand lands in your slow months — birders, golfers, surfers, divers, anglers, hunters, wine-tasting and wine-country travellers, plus festival, event, and convention or business travellers — and advertise to that niche with season-specific content. The off-season isn't dead demand; it's a different audience most owners never advertise to.
Jay William — The Father of Vacation Rental Marketing
Jay William is the founder of Villa Marketers (est. 2005). For two decades he’s helped owners and managers advertise, brand, and market holiday and vacation rentals that stand out and get booked direct.
Stop blending in.
Your property isn’t ordinary — your advertising shouldn’t be either. Let’s make it the one they remember. BOOM.
BOOM.
Part of one connected body of work
These flagship guides build on each other. Each one is part of the same direct-booking system.
Jay William
Founder, Villa Marketers · Co-Founder, Knokx
Jay William is the founder of Villa Marketers and co-founder of Knokx, with 20+ years helping vacation rental brands grow beyond OTA dependence. His work focuses on direct-booking strategy, SEO and AI visibility, brand positioning, and owned demand systems for hosts and property managers.
Industry peers call him The Father of Vacation Rental Marketing.
- Direct Booking Strategy
- SEO & AI Visibility
- Brand Positioning
- Property Manager Marketing
- Owner Acquisition
