How to master direct booking: Expert strategies for booking autonomy 

Distribution across the vacation rental industry has reached a turning point. While OTAs are a vital source of distribution, establishing your own brand presence builds resilience and gives you more control over guest relationships, pricing strategies, and brand experience, altogether creating long-term value that compounds over time 

At our recent industry conference, GuestyVal, industry leaders from Red Cottage, StayFi, and Wander shared battle-tested strategies for driving direct bookings and building lasting guest loyalty.

The brand recognition problem

Here’s a telling exercise: If you’re planning a trip, which airline will you use? Most people can name their preferred carrier. Which hotel chain? Again, most will have a clear favourite. But when it comes to vacation rentals, many travelers default to “I’ll check Airbnb.”

According to Arthur Colker, CEO and founder of StayFi, this isn’t just a marketing problem. It’s a fundamental business vulnerability. When guests remember the platform instead of your brand, you’re building brand value for someone else. Every five-star review, every exceptional experience, every personalized touch may get attributed to the OTA, not to you.

Colker recommends creating 6-8 brand impressions during each stay. “So while they may come saying they booked an Airbnb, we want to make sure they leave saying they booked your brand, your property.” 

Creating brand touchpoints that matter

Building brand recognition requires strategic repetition throughout the guest journey. Smitha Achar, guest success manager at Wander, noted that even the smallest takeaways can leave a long-lasting impression with guests. 

Physical presence

Something as simple as a branded pencil and notepad can create lasting brand associations that influence future booking decisions. Custom notepads, branded fridge magnets, welcome gifts, and house-specific merchandise all serve as tangible reminders of your brand. 

Digital integration

Digital touchpoints such as QR codes linking to your direct booking site, branded guidebooks in your Guest App, and consistent visual identity across all communications reinforce who they’re really staying with. 

Branded properties 

Some property management companies go a step further by branding each house with its own name and character. According to Archer, guests would remember the house name and share it on social media, which is fast becoming the next frontier of STR distribution.  

Personal connection

Matthew Orley from Red Cottage emphasized that every guest interaction, from booking confirmation to concierge service, should prominently feature your brand name, not generic vacation rental terminology. 

The key is making these touchpoints feel natural and valuable, not like aggressive marketing. Guests should appreciate the branded elements because they enhance their experience, not tolerate them despite the branding.

The power of membership programs

Traditional hotel chain loyalty programs don’t translate well to vacation rentals as guests rarely accumulate enough stays to make points feel meaningful. Membership programs flip the model entirely.

Red Cottage’s $500 annual membership exemplifies this approach with compelling benefits:

• 10% discount on all stays
• Waived cleaning fees for longer bookings
• 20% off newly launched properties for the first 30 days
• Extended booking windows for non-members
• Concierge services and surprise gifts

The results speak volumes: 20% of members stayed three or more times in the first year, with one guest booking eleven different properties in twelve months.

The psychology is identical to airline status programs. Once you’ve invested in membership, you’re significantly less likely to comparison shop. The membership fee itself creates sunk cost commitment, while the ongoing benefits ensure members check your inventory before even considering OTAs.

Beyond the booker: The multi-guest opportunity

Hotels typically serve one or two guests per booking. Vacation rentals regularly accommodate 5-15 people, yet most operators focus exclusively on the booker. According to Arthur Colker, this represents a massive missed opportunity. “It’s important to broaden out and find ways to engage every guest during the stay.” 

Every guest in the property is a potential future customer. Smart operators engage the entire party through: 

Targeted upsells

Not everyone wants early check-in, but someone in a group of ten might want a private chef experience, a mid-stay cleaning, or extended checkout to enjoy a final vacation day.

Inclusive communication

Guest apps and messaging systems should address the whole party, not just the person who made the reservation. 

Experience personalization

Different guests have different needs. Parents might value quiet hours and kid-friendly amenities, while others in the group want restaurant recommendations or adventure bookings.

This approach lets you build your database with every guest, not just the person who booked. Each collected email is a future direct booking you control. 

The email marketing non-negotiable

Colker brought up an uncomfortable truth for property managers: The timeframe of any given past guest actively planning a trip to your destination is vanishingly small, often just a few days out of 365.

This makes consistent communication essential. “You need to make sure that you are appearing in their inbox or text message marketing at least once a month. When they are in the market, they’ll go to Airbnb, but they’ll also check your site to compare rates. So make sure that you’re staying top of mind consistently.” 

At minimum, guests should hear from you monthly, whether through: 

• Automated drip campaigns
• Templated newsletters highlighting seasonal offerings
• Peak booking windows notifications for loyal guests
• Local event calendars and destination content

Many property managers abandon email marketing because they lack dedicated staff. The solution is automation with personalization. Pre-built email sequences can maintain consistent touchpoints while appearing tailored to individual guest interests and booking history.

Strategic upselling: Revenue you’re currently leaving on the table

Smitha Achar from Wander noted that most property managers underestimate how much revenue they lose by not systematically offering upsells. The key is making these offers seamless and conversational, not transactional.

High-converting upsells include:

Time extensions: A $50 late checkout may seem expensive, but a $100 full-day extension that eliminates the morning rush and opens up travel flexibility represents real value, especially if it helps you fill a gap night. 

Mid-stay services: Families staying more than a week often welcome mid-stay cleaning services rather than handling it themselves during vacation. 

Arrival enhancements: On-site greeters serve double duty, providing personalized service that guests value while giving you visibility into larger groups that might pose risks.

Experience packages: Local experiences, private chefs, grocery delivery, and attraction tickets all generate additional revenue while deepening the relationship with your destination.

The operational key is reducing friction. Guests should be able to add these services through email links, app interactions, or simple text responses, not lengthy phone calls or complicated booking processes. 

Opening your calendar strategically

Peak dates like July 4th, Christmas, and New Year’s represent your highest-value inventory. Yet many property managers immediately list them across all channels, letting OTAs capture the most profitable bookings.

The smart approach is to offer exclusive early access to your direct audience. Email past guests and members 30-60 days before pushing to OTAs, positioning it as a VIP benefit: “Because you’ve stayed with us before, you get first access to our premium holiday dates.”

This strategy delivers multiple benefits:

• Direct bookings at higher prices without OTA commissions
• Longer advance bookings that improve cash flow
• Reinforced loyalty through exclusive access
• Higher perceived value of being in your database

If your prime inventory fills directly, you win.. If it doesn’t, you still have OTA distribution as a backstop.

Finding the right direct-to-OTA balance

There’s no universal “right” percentage of direct bookings. It depends on your market, booking windows, and business model. However, industry operators generally agree that:

60-70% direct represents a healthy, sustainable mix for established operators. This provides strong margin protection while maintaining OTA distribution for incremental demand.

100% direct often means you’re leaving bookings on the table. Unless you’re consistently sold out with wait lists, pure direct strategies may be artificially constraining your growth.

Sub-30% direct suggests dangerous platform dependence. You’re vulnerable to algorithm changes, commission increases, and losing direct relationships with your guests.

The goal isn’t to eliminate OTAs, but control your own destiny by building direct channels that capture your most valuable bookings while using OTAs strategically for fill and market expansion.

Subtle billboarding: Making OTA listings work for direct bookings

Guest sophistication is increasing, and more travelers actively google listing names to find direct booking options, comparing prices across channels. According to Arthur Colker, operators can gently guide this behavior with subtle billboarding across OTAs. 

Photo optimization

Services like BoxBrownie can digitally insert your logo onto TVs, coffee mugs, or throw pillows in listing photos for under a dollar per image. These plant visual cues that guests remember when searching.

Name consistency

Your listing name should match across all channels. When guests google “Red Cottage Hudson Valley Estate,” your direct site should appear in the top five results, making price comparison effortless.

Description language

While respecting platform terms, your listing copy should reinforce your company name and brand story, not generic property features. 

The goal is to ensure that guests who want to book direct can easily find you, even if they initially discover your property on an OTA.

Measuring what matters

You can’t optimize what you don’t measure. Yet many property managers struggle with attribution, making it impossible to calculate ROI on direct booking initiatives.

Start simple:

Promo codes 

Different codes for email campaigns, social media, and paid advertising instantly show which channels drive conversions.

Google Analytics with e-commerce tracking

Understanding traffic sources and conversion paths is essential, though it requires some technical setup. 

Member retention metrics 

Track not just membership sales, but second and third bookings within the membership year. This shows whether the program genuinely drives loyalty or just one-time purchases.

Cart abandonment recovery

Specialized tools in the Guesty Marketplace capture thousands in recovered bookings weekly by retargeting guests who started but didn’t complete reservations.

For influencer partnerships and press placements, establish attribution mechanisms before the campaign launches. Without promo codes, unique URLs, or tracking pixels, you’ll never know if that magazine feature or influencer post actually drove bookings. 

The long game: Building brand value

Your direct booking strategy is about building assets that appreciate: a guest database that grows as your brand recognition strengthens. Your acquisition costs drop with every repeat booking. The advantage builds over time. 

The property managers winning this game share common characteristics:

• They invest in brand identity as seriously as operational excellence
• They view guest data as strategic infrastructure, not a contact list
• They create loyalty through value and exclusivity, not just discounts
• They measure attribution and optimize based on actual performance
• They think in systems and automation rather than one-off campaigns

Most importantly, they recognize that reducing OTA dependence builds a more resilient, profitable business that isn’t beholden to algorithm changes or commission increases.

The vacation rental industry is maturing. The operators who thrive in the next decade will be those who transform transactional bookings into lasting guest relationships that drive direct revenue, reduce acquisition costs, and create genuine brand equity.