What 8 Vacation Rental Marketing Audits Reveal About Winning (and Losing) in Today’s Market

Let’s call it what it is…

The short-term rental and glamping markets are in the middle of a seismic shift, and most owners are feeling it whether they admit it or not.

Travelers have leveled up. They’re not just “savvy” they’re surgical, using tools like ChatGPT, Google’s AI Overviews, and Perplexity to slice through the noise and find exactly what they want. Meanwhile, the old playbook of “just list it everywhere and hope for the best” is doing more harm than good. Quickly revealing, OTA dependency isn’t just lazy; it’s quietly stripping away your brand equity, guest after guest, booking after booking.

I’ve spent the last seven years in the trenches of the hospitality industry, from running a DMO to scaling a glamping resort from a half-dozen treehouses to a 21-unit, 93% direct-booking powerhouse. If there’s one thing I know, it’s this: Marketing is about owning your audience, not renting it. That’s why I followed a hunch.

I wanted to see if what I’ve been feeling matches what’s happening on the ground.

So I rolled up my sleeves and ran marketing audits on eight very different properties—typically a paid service, but this time I offered them complimentary to fellow American Glamping Association members during a private, first-come, first-served lunch-and-learn training session.

Among the participants were boutique B&Bs, glamping resorts, and even some franchise models like KOA. Then I layered in fresh industry data—like the GBTA 2025 Business Travel Index which just reported that arts, entertainment, and outdoor recreation are driving the biggest jump in travel demand since 2019.

Here’s what the data—and my gut are telling me:

Demand is up, yes, but most owners are still playing the wrong game. They’re trapped in an endless race to the bottom on price, blending in instead of standing out, and letting OTAs “own” their guests.

The result? Too many owners don’t build relationships.

They rent them. And when algorithms change or commission rates spike, they’re left scrambling for last minute bookings. 

Here’s my hypothesis: If owners put half as much energy into building their own visibility and trust off the platforms as they do optimizing on them, they’d see better guests, more direct bookings, and real brand resilience. No more being held hostage by someone else’s audience.

So, what’s actually working—and what’s quietly killing your revenue?

This audit pulls back the curtain and together we’ll look at:

  • What top-performing operators are actually doing differently

  • Where most managers are bleeding money (often without realizing it)

  • Simple, strategic steps to build a future-proof direct booking pipeline

Think of this as your no-nonsense, quick-scan playbook for winning in today’s market—on your terms, not the OTAs’.

How a Vacation Rental Marketing Audit Uncovers the Biggest Gaps

Taking a closer look at the marketing strategies behind Bosco Bracco, Blue House B&B, Open Sky, The Canyon Pond Creek, Columbia Gorge Getaways, Two Capes Lookout, Point South KOA, and ReTreet Resort & Spa revealed a clear—and surprisingly consistent—pattern. Each of these properties brings something special to the table, yet most are missing out on bookings and long-term guest loyalty due to basic, avoidable missteps.

For many, the booking process is still confusing and clunky on mobile, leaving guests frustrated and far more likely to abandon their reservations. Several are missing critical opportunities to capture leads. Either by skipping effective pop-ups, neglecting to offer seasonal incentives, or simply not making it easy for guests to stay in touch.

Despite using words like “luxury,” some properties fail to back up that promise with strong visuals or real guest stories—leaving potential guests unconvinced. A number of operators, including some who’ve been featured in local press or partnered with tourism boards, aren’t leveraging those trust signals anywhere on their sites.

And perhaps the most urgent gap: only a select few—like Blue House B&B and Two Capes—have adapted to the new world of AI-powered search. The others remain virtually invisible on platforms like ChatGPT and Perplexity, missing out on high-intent guests who rely on conversational search to plan their travels.

Bottom line: The gaps we uncovered aren’t just about tech—they’re about strategy, mindset, and execution.

The best part? Every one of these challenges is entirely fixable, starting right now.

What the 8 Vacation Rental Marketing Audits Uncovered

  • 88% of properties had clunky mobile booking flows that risked high abandonment rates
  • 75% lacked an active lead capture funnel (pop-ups or discounts) despite offering seasonal deals
  • 62% used the word “luxury” without aligning visuals and storytelling to support it
  • 50% failed to integrate press mentions or tourism partnerships on their websites
  • Only 25%  had agentic search visibility in ChatGPT & Perplexity results
vacation rental marketing audit results

Industry Context: How Travelers Behave

  • 📊 72% of travelers now use AI tools to research stays (Skift, 2024)

  • 📊 Guests are 5x more likely to book after seeing user-generated content on social media (Expedia, 2023)

  • 📊 Email leads convert at 34% when paired with a clear discount offer (HubSpot, 2024)

Is Your Property Invisible? Invest in a $1,500 Visibility Audit and Find Out

Each audit highlights unique opportunities and challenges, capturing both how these properties show up through the eyes of a guest and what’s happening behind the scenes. A full 360-degree vacation rental marketing audit is now available for owners who want the complete picture—a deep dive into both your guest-facing experience and the inner workings of your systems. Discover exactly where your property shines and where it can be optimized for performance. 

While that’s available privately, let’s take a look at one of the public audits that pulled back the curtain on what’s really working and what’s holding properties back. This particular audit revealed several key best practices that top-performing operators consistently follow, along with some surprisingly common mistakes that are easy to fix. These aren’t just “nice to haves” they’re the kind of quick wins that, when implemented, can drive an immediate shift in visibility, guest trust, and direct booking performance.

Top 5 Best Practices: The Gold Standard in Marketing for Driving Direct Bookings

If these live looks at bookable properties have taught us anything it’s that today’s travelers aren’t just browsing, they’re curating. They’re turning to AI tools for inspiration, scanning social feeds for proof, and making decisions based on relevance, not just availability. It’s not enough to be found—you have to be chosen, trusted, and talked about. In this environment, the gold standard in marketing isn’t about who shouts the loudest it’s about who shows up the most meaningfully.

That means:

  • Being present in the channels where real decisions are made (and yes, that now includes AI-driven search and social media)

  • Creating guest-centric content that builds belief and emotional buy-in before someone hits your booking page

  • Capturing leads early and nurturing them with real value, not just a promo code tossed in desperation

Direct bookings don’t happen by luck. They happen when visibility, trust, and timing collide. This vacation rental marketing audit section breaks down exactly how to align your marketing efforts with how modern travelers behave so your brand becomes their obvious next stay.

 

1. Agentic Search Optimization

Example: Two Capes Lookout ranked #1 for “Top Glamping Oregon Coast” in ChatGPT.

  • Why It Works: Guests are shifting from Google to AI-driven search tools. Properties with PR backlinks and strong SEO win visibility.
  • Quick Action: Build a “Press & Media” hub on your site and secure 3+ regional backlinks within 90 days.

2. Frameless, Simple Booking Flows

Example: Two Capes Lookout‘s mobile and desktop booking UX was frictionless and included thoughtful guest data collection (reason for stay, arrival time).

  • Why It Works: Guests convert when they feel guided and reassured.
  • Quick Action: Audit your booking flow for mobile clarity and remove unnecessary steps or distractions.

3. Seasonal Video + Creator Content

Example: Blue House B&B showcased guest stories and consistent branding across Instagram.

  • Why It Works: Videos and UGC (user-generated content) humanize a brand and expand organic reach.
  • Quick Action: Schedule quarterly videography during peak seasons and partner with 3 creators/year.

4. Email Lead Magnets That Actually Work

Example: Two Capes Lookout offered a 10% discount but could amplify its visibility and design.

  • Why It Works: A strong pop-up converts warm traffic into bookings.
  • Quick Action: Add an exit-intent pop-up with a compelling CTA: “Unlock 10% Off Your Next Adventure.”

5. Tourism & Community Partnerships

Example: Point South KOA actively promoted local events and built synergy with their community.

  • Why It Works: Tourism boards are legally required to reinvest lodging tax dollars into marketing.
  • Quick Action: Contact your local tourism board to ensure your property is listed and ask about cooperative marketing opportunities.

Trends Shaping the Short-Term Rental Industry

The way guests discover and choose where to stay is undergoing a seismic shift.

Search engines are being replaced by conversational platforms like ChatGPT and Perplexity, where brand visibility depends less on keyword stuffing and more on reputation, relevance, and backlinks. Meanwhile, influencer-driven content has become a first stop for trip planning—not an afterthought. Travelers are no longer just looking for a place to sleep—they’re seeking meaningful, nature-rich experiences that feel rooted in community and purpose. And behind the scenes, savvy operators are quietly pulling back from OTA dependence, investing instead in systems they own: direct booking flows, email lists, and guest-driven storytelling.

The landscape is evolving fast—and those who adapt early will be the ones who lead.

  • AI-Driven Search: Agentic platforms (ChatGPT, Perplexity) are replacing blue links. Properties with PR backlinks win.

  • Creator Economy Influence: Influencer content now drives 27% of first-time bookings (Expedia).

  • Sustainability + Experience Demand: Guests want immersive nature-based experiences with small-business charm.

  • Shift Away from OTA Dependence: Direct booking engines and email lists are regaining priority.

 

What this audit made clear, and what broader short-term rental trends continue to confirm is that guest behavior has evolved faster than most operators have adapted. AI-powered search, creator-driven trip planning, and rising demand for authenticity mean that visibility alone isn’t enough. You need relevance and trust. That’s why I’ve included a 90-day visibility playbook designed to help owners shift from reactive to strategic, driving fresh demand through channels they actually control. It’s packed with simple, high-impact actions that meet today’s traveler where they are and guide them straight to your booking page.

Your 90-Day Visibility Plan: The Playbook for Direct Booking Momentum

If you’ve been relying on OTAs to fill your calendar, this is your turning point. The path to more direct bookings isn’t built overnight. It’s built in focused, strategic sprints. This 90-day playbook lays out exactly where to start and what to prioritize, from foundational fixes to visibility upgrades that actually convert. Whether you’re running a boutique glamping resort or managing multiple short-term rentals, these actions are designed to move the needle fast. Think of it as your reset button—one that puts your property back in front of the right guests, in the right channels, with the right message.

Ready to shift from invisible to unforgettable? Start here:

✅ Within 30 Days

  • Audit your website for clarity and guest-centric storytelling

  • Fix broken/missing social links and pop-ups

  • Contact local tourism boards for partnerships

✅ Within 60 Days

  • Launch a lead magnet with a 3-part email automation

  • Add a “Press & Media” page showcasing earned PR

  • Test your booking flow on all mobile devices

✅ Within 90 Days

  • Launch creator partnerships with trackable booking codes

  • Schedule seasonal video/photo shoots

  • Optimize Airbnb listing titles for search discoverability

The landscape is changing at lightning speed. AI-driven search, guest expectations, and shifting booking behaviors are rewriting the rules for vacation rental success. Owners who prioritize visibility, trust, and direct guest relationships—not just occupancy—will thrive in the new era.

Ready to take control? Get started with the Power Session that feels right for you.