How Property Managers Can Get First-Time Guests to Book Direct

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How Property Managers Can Get First-Time Guests to Book Direct

As a property manager, have you ever thought that direct bookings are only for returning guests, people who already know and trust your property? But what if you could skip the middleman—Online Travel Agents (OTAs), and get first-time guests to book directly with you as well?

This fresh approach was the focus of Jenn Boyles’ presentation at the
Direct Booking Success Summit 2024. Jenn, a seasoned advocate for the ‘book direct’ movement, also hosts the popular Direct Booking Success Podcast, where she shares extensive insights and strategies for property managers. In her session, she explored how to attract first-time guests to book directly, an invaluable tactic in a market largely controlled by OTAs like Airbnb and Vrbo.

If you’ve ever felt frustrated by OTA limitations or are unsure how to make
direct bookings work, this article will break down Jenn’s proven approach, explain how her strategies apply to property managers, and outline the steps you can take to implement them.

Why Direct Booking Channels Are Essential for Property Managers Seeking Control and Growth

  • With the government mandating VAT collection by OTAs like Airbnb, Vrbo, and Booking.com property managers are likely to face reduced profit margins. This makes it increasingly important to diversify revenue streams and reduce dependency on these platforms.
  • Over-reliance on OTAs leaves businesses vulnerable to algorithm changes, account suspensions, and oversaturation, which can quickly disrupt bookings and undermine a property manager’s ability to stay competitive.
  • Direct bookings eliminate OTA hefty commissions, increase revenue control, and allow property managers to build stronger guest relationships, providing a more reliable and profitable foundation for long-term success.
  • Property managers can focus on branding, marketing, and trust-building to establish a sustainable and independent business model, as these efforts help differentiate their offerings and reduce reliance on external platforms.


The Two Buckets Framework for Attracting New and Return Guests

Jenn explains her strategy using the analogy of two buckets: one for new guests and one for return guests. Both are crucial for sustaining your business, but they require different approaches.

  1. The Return Guest Bucket:

According to Jenn, Return guests are your easiest wins. These are people who’ve already stayed with you and experienced your hospitality. With the right nurturing, they can turn into loyal customers who provide reliable, repeat income.

Action Steps for Property Managers:

  • Actively collect guest data during or after their stay, such as email addresses and preferences.
  • Use email marketing to stay in touch, sending periodic updates, special offers, or personalized messages.
  • Provide incentives for returning guests, such as discounts or exclusive perks for booking directly.
  1. The New Guest Bucket:

Attracting new guests is more challenging but essential. Many property managers depend entirely on OTAs to fill this bucket, which Jenn warns is a dangerous strategy. Guests who book through OTAs aren’t “yours”, they belong to the platform. This makes it difficult to nurture these guests into repeat customers.

Action Steps for Property Managers:

  • Diversify your booking sources to reduce reliance on OTAs.
  • Focus on building your own ecosystem, your website, email lists, and social media channels.
  • Treat OTAs as a supplementary tap rather than the sole source of new bookings.


The Role of Trust in Direct Bookings and How to Build It for Your Business

Jenn emphasizes that trust is the single most important factor in convincing guests to book directly. OTAs like Airbnb succeed because they’ve built systems like AirCover to instill confidence in guests. Property managers must replicate this trust-building process independently.

How Property Managers Can Build Trust:

  1. Personal Connection

Guests are more likely to trust people than faceless companies.

  • Include photos of yourself and your team on your website and social media.
  • Write a detailed “About Us” page explaining your story, values, and local expertise.
  • Use social media to showcase your personality, highlight guest experiences, and interact with potential guests.
  1. Transparency

Guests want to know what to expect.

  • Be upfront about policies like cancellations, refunds, and guest protections.
  • Dedicate a page on your website to explaining why guests can trust you (e.g., certifications, insurance, guest reviews).
  • Property managers can create a branded initiative like Airbnb’s AirCover, bundling policies into a comprehensive guarantee to build trust and provide protection against issues like property damage or cancellations.
  1. Social Proof

Positive reviews and testimonials are powerful trust signals.

  • Feature reviews prominently on your website, especially with photos of guests (with their permission).
  • Highlight awards, certifications, or memberships in local or industry organizations.

How Visibility Drives First-Time Guests to Book Direct with You

Jenn says that visibility is the first step in converting new guests. Without visibility, guests can’t discover your property. She outlines several ways property managers can make their properties more discoverable:

  1. Optimize OTA Listings:
  • Use your brand name in your listing titles and descriptions to encourage guests to search for your direct website.
  • Include unique features that make your property stand out, like “Rose Cottage at Sunset Beach.”
  1. Social Media Marketing:
  • Post consistently on platforms like Instagram, Facebook, or Pinterest.
  • Share content that highlights your property’s unique features, local attractions, and guest experiences.
  • Use clear calls to action to guide followers to your website.
  1. SEO (Search Engine Optimization):
  • Optimize your website for local keywords (e.g., “family-friendly rentals in Charleston”).
  • Write blog posts about your area, such as “Top 10 Things to Do in California” or “Hidden Gems in California.”
  • Ensure your site is mobile-friendly and loads quickly.
  1. Referrals:
  • Encourage guests to recommend your property to their friends and family.
  • Offer referral discounts or other incentives to both the referrer and the new guest.

How Email Marketing & Lead Magnets Can Build Guest Loyalty

Jenn emphasizes the power of email marketing to nurture both new and returning guests. Rather than simply asking for newsletter sign-ups, she recommends offering something valuable in exchange for email addresses.

Ideas for Lead Magnets:

Destination Guides: Highlight the best attractions, restaurants, and activities in your area.

Packing Lists: Provide packing recommendations tailored to your property (e.g., ski gear for winter lodges).

Discount Codes: Offer exclusive discounts for first-time bookings.

Itineraries: Create sample itineraries for families, couples, or solo travelers.

Once a guest is on your email list, send a nurture sequence of 3–7 emails. These emails should build trust, provide value, and subtly encourage bookings.

The Key Elements Every High-Converting Direct Booking Website Needs to Have

Your website is the backbone of your direct booking strategy. Jenn stresses the importance of a professional, user-friendly website that guides potential guests seamlessly from discovery to booking.

  1. High-Quality Images: Invest in professional photography to showcase your property.
  2. Clear Navigation: Make it easy for guests to find information and book directly.
  3. Trust Indicators: Add badges, reviews, and policies that reassure guests.
  4. Mobile Optimization: Ensure your website looks great and functions well on mobile devices.
  5. Fast Loading Speed: A slow website can lead to lost bookings.


Conclusion

As 2025 approaches, the vacation rental market is only growing more competitive. Relying solely on OTAs like Airbnb and Vrbo for short-term bookings may provide convenience, but it also comes with steep trade-offs: high commissions, limited control over your bookings, and the constant uncertainty of changing algorithms and policies.

Creating a direct booking channel isn’t just a smart move, it’s a necessary one. It’s about more than bypassing the middleman; it’s about establishing a business model that’s truly yours, one that offers stability, profitability, and full control. By building a direct booking strategy, you’re investing in the long-term success and independence of your vacation rental business.

Ready to make direct bookings your priority in 2025?
The Direct Booking Summit 2025 is on the horizon! If you want to be part of it, click here to register yourself on the waitlist.