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
- 12 min read
- Reviewed for Accuracy
- 2026
Everyone repeats location, location, location. It isn’t wrong — it’s just where most buyers stop. The winners find demand the competition hadn’t, see what a property could become, refuse to be a commodity, confirm the boring fundamentals (legality, real numbers, access), and make sure the finished property can actually be found and booked. Do those, and you buy a business. Skip them, and you buy a mortgage.
We helped Chris Moran name and launch Oxford Vacation Rentals — brand and domain included — compete at the top of a high-demand market, and target affluent travelers. We built that portfolio until the company was acquired. Then Chris came back and did it again: we helped launch Beach Stays Vacations and grow it to a real portfolio before it, too, sold — his second brand built with us, all the way to exit. He’s said as much in his reviews. The principles below are the ones that did it.
“I just completed my second project with Villa Marketers and am once again so pleased with how the site looks and how it functions… I want to drive as much direct booking traffic as possible and the site makes it easy for guests to secure their booking.”
Everyone repeats the same three words: location, location, location. It’s not wrong — it’s just where most buyers start and stop. After twenty years in this industry, the owners who win rarely found the “best” location on the map. They did three things other buyers didn’t: they found demand the competition hadn’t, they saw what a property could become, and they refused to be a commodity.
Here’s how to play it — starting with the parts nobody tells you, then the fundamentals you can’t skip.
The winners rarely find the “best” location on the map. They find the demand no one else did — then refuse to look like everyone else.
1. Find demand the competition hasn’t found yet
Obvious tourist markets are obvious to everyone. You buy in expensive and then compete against a thousand identical listings. The edge is a market where demand outruns competition — usually one that isn’t on the tourist radar at all.
The best ones share a pattern: recurring, non-tourist demand. People who need lodging regularly, not just in July. University towns are the cleanest example — a market like Oxford has thin tourist competition, but visiting parents, academics, and event weekends keep demand steady year-round. The same is true of areas near convention centers, hospitals, military bases, and large employers. Anchor demand doesn’t dry up off-season, and it’s far less crowded than the beach or theme-park circuit.
A niche location with steady under-served demand can outperform a trophy market you overpaid to get into.
2. Study the competition — then refuse to be them
Before you buy, study who’s already renting there. Pricing, photography, positioning, reviews. Not to copy — to find the gap they all left open. When listings look the same, the one that shows up different wins.
Know the going rates and standard presentation cold, so you can deliberately break from it. The question isn’t “how do I match what’s out there” — it’s “how do I come from an angle no one else has, and create demand of my own.”
3. Match the rental model to the demand — and use the seasons on purpose
Don’t assume only nightly stays. Blend short-term and mid-term based on who actually needs the space. Traveling professionals, relocating families, students, and medical stays want 30-plus-day bookings — steadier income, less turnover, less wear.
Treat seasonality as strategy. In Florida, snowbirds: mid-term to Northerners escaping winter, then flip to short-term travelers the rest of the year. The calendar keeps earning. Map who fills which months before you buy.
4. Buy the potential, not just what’s there
Most people see what’s in front of them; you have to see the finished form. A backyard you could turn into an outdoor living haven — dining, lounging, a fire feature. A blank wall that becomes a mural guests photograph. A water feature over the pool. A few well-chosen amenities can make a property one-of-one — and a one-of-one property competes on being the only one like it, not on price.
A one-of-one property competes on being the only one like it, not on price. Forced appreciation and a marketing moat in the same move.
Ask: what could I do here that no one else in this market has done?
5. Use the data — but don’t let it cap your imagination
Pull the market numbers. Tools like AirDNA show revenue, occupancy, and seasonality — use them. Their blind spot: they measure what already exists, priced into tidy categories. They can’t score the property that doesn’t fit the mold yet — the one you’re going to make one-of-one.
The biggest returns live in the gap between what the data calls normal and what you can create. Use data for the floor. Imagination for the ceiling. The goal isn’t a slightly-better commodity — it’s the purple cow, remarkable enough that demand comes looking for you.
Sometimes you’re simply in the right place with a high-demand property and do well on that alone — but a real differentiator is the stronger hand.
6. Buy where people already search
Travelers search specific communities and areas by name. Buy inside a community people actively look up, and you’ve bought built-in discoverability — demand that arrives already knowing where it wants to be.
Before signing, know whether the area is one guests search for on purpose or one you’ll spend years teaching them exists. Both can work — but they are very different businesses.
7. Does the property have a story?
A property with a story is worth more and markets itself. Sometimes the story is already there — history or character, a place that hosted something, the oldest of its kind, a property with a name. Sometimes you create it — a new build positioned as a genuinely eco-friendly stay, for example.
A story gives guests a reason to choose you over the identical box next door, and it gives you a marketing hook that compounds. Blank, storyless properties are the hardest to make stand out later.
8. Know your guest — and your own intentions — before you buy
Two honest decisions before you fall in love with a listing.
Who is this for? Young couples, three-generation reunions, remote workers, international travelers, affluent luxury guests, or the recurring-demand crowd. Pick the guest first, then judge every property against them. Targeting affluent travelers, done right, lifts the whole economics. A place for everyone converts for no one.
What do you want? Pure investment or a home you’ll also use? Do you actually want to manage it? Every personal-use week is a booked week given up, and “self-managed” is a real job. Decide now — it changes which property is right.
9. Then confirm the fundamentals — don’t skip these
Legality. The factor that didn’t exist in 2011 and now sinks the most deals. Short-term rental rules — permits, caps, primary-residence requirements, HOA and zoning, local taxes — vary address by address and keep changing. Confirm in writing what’s legal at that exact address today, and where the rules are heading. A property that can’t legally operate is a liability with a view.
The real numbers. Beyond market data, model your full cost stack — mortgage, insurance (much higher in storm and flood zones), taxes, management, cleaning, utilities, furnishing, maintenance — against a conservative year, not a dream one. No national averages. Get the local data.
Access twice over. Can guests reach the property, and can they reach the experience they booked for — the beach, the campus, the convention center, the trailhead? You’re selling the trip, not the drywall.
10. And the piece most buyers forget: can you get it found and booked?
Two identical homes on the same street earn differently depending on whether the owner can market and book them. A great property still fails if no one can find it — and “found” now means being what search engines and AI assistants recommend when a traveler asks where to stay.
“List it and hope” means renting your business from someone who can raise your costs or bury you at will. The winners drive direct bookings. That’s the part we do — and the part that turned Oxford Vacation Rentals and Beach Stays into exits.
The buyer’s checklist
- Demand vs. competition (under-served, ideally recurring?)
- Competitive angle (know their pricing/photos/positioning to differ?)
- Rental model & seasons (blend that fills the calendar?)
- Potential (what could this become?)
- Data & vision (AirDNA for the floor + a plan for the ceiling?)
- Searchability (searched by name?)
- Story (has one / can you give it one?)
- Guest & intentions (who's it for, do you want to run it?)
- Legality (in writing, exact address)
- Numbers (real comps, conservative, full stack)
- Access (property + experience)
- Marketability (real path to visibility + direct bookings)
FAQ
Is location the most important factor when buying a vacation rental?
Location sets your ceiling but isn't the whole answer. Whether demand outruns competition, matching the right rental model to that demand, the property's untapped potential, legality, real numbers, and marketability all determine whether that ceiling is reached. Some of the best buys are under-the-radar markets with steady recurring demand rather than crowded trophy locations.
What is an under-the-radar vacation rental market?
An area with strong, often year-round demand but relatively little competition, frequently driven by recurring non-tourist needs. University towns and areas near convention centers, hospitals, or large employers often have steady lodging demand with far fewer competing listings than beach or theme-park markets.
Should I buy for short-term or mid-term rental?
It depends on local demand. Many strong investments blend both — short-term nightly stays plus mid-term 30-plus-day bookings from traveling professionals, students, medical stays, or seasonal guests like snowbirds. Mapping which segments fill which months before buying keeps a calendar earning year-round.
How do I make a vacation rental stand out instead of competing on price?
Study the competition's pricing, photos, and positioning to find the gap they've left, then deliberately differentiate with a signature feature, distinct design, a clear story, or a specific audience like affluent travelers. Market-data tools like AirDNA show the standard; the goal is to create something remarkable that doesn't fit the standard so demand comes to you rather than competing on rate.
How do I add value to a vacation rental property?
Buy for potential, not just current state. Turning a backyard into an outdoor-living space, adding a signature feature like a mural or water feature, or giving the property a genuine story or positioning such as an eco-friendly stay can make it one-of-a-kind, so it competes on uniqueness rather than price.
Does a good location guarantee bookings?
No. Two identical homes on the same street can earn very differently based on how well each is marketed, made discoverable, and set up for direct bookings. Location makes success possible; visibility and marketing make it happen.
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 turn properties into businesses that get found and booked — independent of the big platforms — including naming and building brands all the way to acquisition.
Buy the property. We’ll make sure it gets booked.
You find the place with demand and potential others missed — let’s make sure the world can find it. 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
