Mapping Your Content for the 4 Stages of Vacation

Written By: Conrad
Last Updated: September 8, 2023

This post is part two of a two-post series on vacation rental content that reaches guests throughout their entire booking journey. In our first post, we laid the foundation for a multi-step content marketing strategy. In this post, we’ll offer actionable ways to engage with guests at every step.

In preparation for the busiest booking season of the year, Guest Hook is here to give vacation rentalists a two-part primer on the 4 Stages of Vacations and how you can use them to boost your bookings. Don’t rely on one-size-fits all marketing; grab guests at all stages, from Daydreaming to Booking.

In part two below, we’ll talk explain what the four stages are.

Stage 1: Daydreaming

Daydreamers are embarking on the first phase of vacation: good old escapism. They’re scrolling through Instagram travel photos between emails at work, or filling their screens with beach shots on a chilly winter evenings on the sofa.

In this phase, potential guests are likely just clicking around at random (or discovering content by accident—think social media posts from vacationing friends) vaguely wondering if a trip is within their budget.

Sometimes daydreamers will have a destination in mind; other times, the idea of just going somewhere—anywhere—is all the daydream fuel they need.

How to hook Daydreamers:

  • Gorgeous images
  • Image descriptions that center on the experience
  • Zoomed-out, image-heavy content, like “How Turks and Caicos Can Cure Winter Blues”

This phase is all about imagery. Daydreamers want to get lost in beauty and possibility. And photos are the quickest route to get there.

One of my favorite procrastination past-times, for example, is typing a destination into Google Images to get a zoomed out view. If you’ve never done this, I highly recommend it. Just head on over to Google, click the Images tab, and type Turks and Caicos, for example. Ahhhhh.

(This is an especially fun during stressful times—like, oh, I don’t know, that week when early December ticks over into mid-December and you haven’t started shopping yet and suddenly you start hearing phrases like “last minute gifts” when it was just Thanksgiving seconds ago. But I digress.)  

Where to hook Daydreamers:

  • Pinterest
  • Instagram
  • Google images
  • Newsletters

ANOTHER HINT: Daydreamers also encompass your past guests. This is where great newsletters to your mailing list come in—they remind guests of the great time they had with you, and get them dreaming about a repeat trip.

Stage 2: Investigating

These travelers have moved from aimless daydreaming to a more focused “investigation” stage. Investigators will have decided that a trip is in budget, and will have picked a destination—yours!—and are now zooming in and making some important decisions. Vacation rental? Hotel? Campground? Center of downtown? Quirky neighborhood a few miles east?

As a vacation rentalist with local expertise, you are very well-positioned to help these travelers  (and in the process, help them find you). Remember: at this stage, the goal is to grab these guests by offering them helpful information, not to convince them to stay with you, specifically. We’ll get there!

How to hook Investigators:

  • Maps, neighborhood guides, transportation advice
  • Content that digs a bit deeper and showcases your expertise, like: “Austin’s Best Neighborhoods, Ranked.”

Where to hook Investigators:

  • Google (using SEO and, specifically, long-tail keywords)
  • Travel websites and media (land a spot in these outlets with PR initiatives—talk to the talented Abode PR if you’re unsure!)

Stage 3: Planning

In the planning stage, guests will have picked their target area. They may have decided to trade in the tent for a comfy vacation rental bed. Now, they’re looking to choose activities, pick their travel dates, price out vacation rentals, and make even more zoomed-in decisions.

We’ve talked a lot about not selling your rental as a cheap option first and foremost. Discounts are great, but shouldn’t be the focus of all of your marketing decisions. For planners, though, we make an exception. In many cases, guests are searching for deals in this stage.

How to hook Planners:

  • Excellent property listings, with high-quality images, sharp descriptions and compelling rates
  • Rich, highly targeted content that speaks to your guest personas [link]: “Five Dog-Friendly Businesses in Point Pleasant”
  • Suggested guest itineraries
  • Newsletters that offer discounts for repeat guests

Where to hook Planners:

  • Listing sites (we’d love all bookings to be direct, but alas)
  • Your website
  • Newsletters

Stage 4: Booking

At last we’ve arrived at this all-important stage, and the smallest part of the funnel—the booking decision. Now it’s not so much about informing your potential guests about your destination, but convincing them that your rental is the best option in that destination.

Now is not the time to think about objective price, so much as to show guests why your rental offers the best option overall. This can be done with things like guest reviews, word-of-mouth referrals, a way-above-average presence on the listing sites and the web as a whole. Brand yourself as the obvious choice.

HINT: If you have a website, you should be guiding guests toward their booking decisions with crystal clear calls to action, like a “BOOK NOW” button and a clear way to search availability. The key is to reduce friction toward a booking as much as possible. Make sure your software is rock solid and that calendars are 100% up-to-date and accurate.

How to hook Bookers:

  • Cultivate stellar guest reviews and testimonials
  • Create a brand that guests trust and recommend to friends
  • Top-notch property photos + descriptions
  • Crystal clear calls-to-action on your website
  • Social proof

Where to hook Bookers:

  • Listing sites
  • Calls-to-Action on your website (a.k.a. “Book Now”)
  • Facebook (now offers a booking option!)

A quick refresher…

Need a simple tool to keep handy when remembering where you should be focusing your content efforts? Refer to our quick guide for content for all steps of the vacation rental booking journey.

Want more help? Talk to Guest Hook. We’ll create a customized solutions report, where we identify opportunities for better content marketing, branding, and copywriting for your business. Hire us to execute the plan, or use it as a guide for your own marketing efforts. Reach out to learn more!

Take The Next Step

  1. Download our free Vacation Rental Marketing Blueprint and watch our FREE training on how to build an actionable, advanced marketing plan for your rental properties.
  2. If you want to learn more about how to generate more bookings, visit our blog and read our articles. 
  3. To get started working with us, visit our contact page, complete the form and schedule a call.
  4. If you’ve found this article helpful, please share it with your friends, team or other vacation rental owners/hosts!

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