The 8 Stages of the Vacation Rental Guest Journey

What does the guest journey have to do with marketing your vacation rental?

Our answer: everything.

While certain marketing strategies will be a better fit for some vacation rental companies than others, most share the same foundational goals: more guests, more repeat and referral guests, and more 5-star reviews.

If you want to make sure your vacation rental business is a success, it’s imperative to create an extraordinary guest experience from the moment they discover you online to long after they’ve returned home. It’s not new news for any of us that guests today are expecting a more personalized, amenity-rich, and seamless experience — and while your communication should always feel natural and genuine, the planning behind the scenes needs to be intentional.

Their experience with your company is not only when they’re physically staying with you, but it encompasses their entire journey. We break this down into 8 different stages:

1. Research and Brand Awareness
2. Inquiry
3. Booking
4. Pre-Arrival
5. Check-In / Arrival
6. During Their Stay
7. Check-Out / Departure
8. Post-Stay

While this can seem overwhelming when formulating your guest experience, it all boils down to preparation and planning. We’ve compiled an assessment of these 8 stages, including recommendations and examples of what you can implement within your vacation rental company during each phase.

Stage One: Research and Brand Awareness

The research and brand awareness stage is where your prospective guest has decided they want to go on their next vacation and begins researching. This typically happens online for most, which is especially true for the Millennial generation and Gen Z (also known as zoomers). They may be exploring new destinations altogether or looking for what will maximize their experience in a specific area they already have in mind.

You’ll often find them searching on Google or social media platforms to explore their areas of interest and will be looking to learn about your area, including events, dining, shopping, and other activities.

Your goal at this stage? Become part of their planning process.

To capture their attention, you need to show up as a trusted local authority with valuable, visually compelling, easy-to-find content. Guest awareness is heavily influenced by your website content, SEO strategies, social media, and broader online presence.

This is also the stage when it’s essential to ensure your listings are fully optimized, from the heading, descriptions, amenities, photography, and more.

Objectives & Goals

Position yourself where they can find you. If this is done correctly, you will become part of their planning phase. Whether they’re dreaming of a relaxing getaway to the beach, an escape to the mountains, or the vivacious city life, your first objective is to appear in your prospective guest’s mind. Once your prospective guest completes this stage, they should feel comfortable and ready to reach out to you. Not your competitor down the street and not one of the OTAs (if they are on your website).

Key Takeaways & Actions

Luckily, we’re here to show you a few ways to get in front of your guests during their research phase! Proven strategies include:

• Having a visually engaging website that’s optimized to convert

• Showcasing inspiring photography and video

• Creating SEO-friendly content with intentionally placed long-tail keywords

• Investing in paid digital advertising to drive qualified traffic to your website

• Offering incentives to join your email newsletter list (travel guide downloads, first-time guest incentives, etc.)

• Maintaining a consistent, engaging social media presence

• Offering an attractive special promotion or discount to spark action

Stage Two: The Initial Inquiry

Your prospective guest is interested enough in your property to send an inquiry; now what? First things first, all the hard work has paid off to grab their attention. Take a step back and celebrate, but only for a quick moment, because it’s time to guide them from interest to booking, and begin building the relationship that turns a first-time guest into a lifelong guest.

While they’ll probably send you an email or give you a call instead of a message in a bottle, the golden rule is to respond as quickly as possible. Timing is key; if your competitor responds before you, you may lose this guest. When you make your responses, you want to be their local expert, so take the time to ask them detailed questions to best fit them with the perfect vacation rental for their specific needs. When you’re asking them these questions, keep track and make notes about what is bringing them to your location (you’ll be using this information later on in their journey).

It’s also crucial to stay transparent when it comes to pricing, amenities, and your overall guest experience. This helps set their expectations appropriately — do they need to bring their favorite K-Cups for the Keurig or even their own linens for the beds?

Objectives & Goals

Your objective in this stage is simple: build trust and guide them confidently toward booking. By the time they leave this stage, they should feel: heard, supported, confident in your professionalism, and certain that you are the right choice for their stay.

Key Takeaways & Actions

While this stage may not be as complex, and this list will be a bit redundant, we wanted to point out a few strategies for you to consider:

• Respond as quickly as possible
• Ask thoughtful questions to start conversation and understand their trip preferences
• Make notes about their vacation to add into your PMS under their reservation for future use (Family or couples vacation? Guys golfing trip? Ladies long weekend? Make a note.)
• Stay transparent about pricing, amenities, policies, and your guest experience
• Make sure they’re able to reach your direct website (#bookdirect)
• Ensure an easy and streamlined booking process online, over the phone, and even in person
• Provide valuable information about your area
• Branding, branding, branding: have a branded signature on your emails
• Get their email at this stage if you’re able and ask them if it’s ok to email them information

Stage Three: Booking Received

Congratulations! Your prospective guest felt confident to book with you and has chosen a property on your rental program that suits their needs. Whether the reservation was created online, over the phone, or in person, you should have all of their contact information and payment (at least for their initial deposit).

Now, let’s make sure they’re happy enough to become a repeat guest and refer their friends to your property. What’s the first communication you have with your guest post-booking? Is it an automated email from your PMS or a text message? Regardless of the type of communication you use, it’s what you communicate that counts. That first impression the guest has needs to be consistent with their pre-booking experience.

Objectives & Goals

Your objective in this stage is to reaffirm their decision and create a seamless transition into the pre-arrival phase. The goal is to eliminate uncertainty and maintain the excitement that led them to book with you in the first place. By the end of this stage, your guest should feel:

• Confident they booked with a professional, organized company
• Clear on what happens next
• Excited about their upcoming stay
• Supported with everything they need

Key Takeaways & Actions

Record all the information within your PMS and send a booking confirmation by email. We challenge you to not only send transactional details but to keep the conversation going and ensure they know when you are available if they have any questions.

Your booking confirmation should include essential details like:

• Arrival and departure dates and times
• Invoice (with additional payment dates if applicable)
• Your contact information
• Design that is consistent with your entire brand

Stage Four: Pre-Arrival

While there is the saying, “if it’s not broken, then don’t fix it,” we believe there’s always room for growth and improvement. What worked 10 years, 5 years… even 3 years ago is not necessarily what guests are expecting now. As our industry continues to grow at a rapid pace, the expectations of our guests also increase. The message we’re all hearing over and over again is that guests are expecting more. They’re expecting more than a hotel experience, and that includes absolute professionalism.

They want to know exactly what to expect when they arrive, and they appreciate receiving helpful information before they even begin packing. This stage is also an opportunity to elevate the guest experience with optional add-ons, personalized touches, and recommendations tailored to their stay.

Objectives & Goals

Your objective in this stage is to prepare your guests for a seamless arrival while reigniting their excitement about the experience ahead. Your goal is to create clarity, reduce pre-trip stress, and build anticipation — all while keeping your communication aligned with your brand.

By the end of this stage, guests should feel:

• Confident they have all the details they need

• Informed about the check-in process and property essentials

• Excited about their upcoming visit

• Supported before they even walk through the door

Key Takeaways & Actions

Plan your messaging! What do you want to include? Here are some ideas:

• General check-in details: check-in time, contact details, and similar information
• Property-specific information: address, access instructions as needed, like WiFi, pool gate, storage areas, etc.
• Amenities and where to find them
• Recommendations for things to do and must-do activities
• Welcome app or where to find the in-property welcome guide
• Personalized video welcome message (this is especially great if you don’t have a physical check-in process)

Stage Five: Check-In and Arrival  

From personalized communications and welcome packets to branded soaps and custom keychains, there are plenty of opportunities to provide a memorable experience for each guest check-in! Some vacation rental companies have a staff member or property manager personally greet their guests upon arrival at the property, which offers the opportunity to walk them through any questions they have about the property. Other companies have switched to an almost fully automated experience, where guests can access the vacation rental via keyless entry with a keycode.

The check-in phase is also a fantastic time to go above and beyond to customize your guest experience. Remember when we said to ask them questions so you could get to know them and make tailored recommendations? This is when you can use that information. Golfing trip? Add a gift package of golf balls and tees. Birthday celebration? Leave a bottle of wine and a hand-signed card at the property.

Objectives & Goals

Supply your guests with all the information they need and add a personal touch. Kudos for making sure to include your brand during this stage. Keep in mind everything you do reflects you and your brand — from the way information is sent and the design to the amenities offered and the tone of voice you use.

Your objective in this stage is to ensure a smooth, stress-free arrival while delivering a warm and memorable welcome. The goal is to create a strong first impression that aligns with your brand and sets the foundation for an exceptional stay.

By the end of this stage, guests should feel:

• Confident in navigating the property
• Welcomed and appreciated
• Supported if they have questions
• Reassured that they are in good hands

Key Takeaways & Actions

Take a look at your check-in process. What could be improved? Do you make it easy for your guests to get the information they need? Have you thought about implementing a welcome package? Does your company have branded items that improve their experience (like local maps, soaps, cooler bags, beach chairs, etc.)?

Whether given during a physical check-in or presented at the property, we recommend having at least a few printed materials within your properties for guests (especially those who may not have access to the other communication you’ve sent).

Stage Six: During the Stay

As we all know, there are multiple types of guests. To roughly break these down, there are those who love communication, those who love simple gestures, and those who do not want to have a conversation at all. More and more guests prefer less contact during their stay (this is particularly true for the Millennial generation and after the pandemic era). So where is the line? Do you make a welcome phone call, send a text, a push notification, or an email? Part of the answer is knowing your guests and target market.

No matter what you decide is best for your company, there should always be a way for easy and quick communication to take place in the event that they need to reach you. Setting expectations is imperative, and having clearly stated times of operation and after-hours procedures in place is very important. What’s worse than a negative review that could have been avoided by a simple conversation during the guest’s stay?

Objectives & Goals

Your objective in this stage is to make it effortless for guests to reach you and ensure they feel supported throughout their stay. Your goal is to create a balance between being accessible and respecting their space — prioritizing guest comfort above all else.

By the end of this stage, guests should feel:

• Comfortable in the property
• Confident they can reach you if needed
• Supported without being overwhelmed
• Fully able to enjoy their stay

Key Takeaways & Actions

Here are ways to optimize the guest experience during their stay:

• Set clear expectations (hours of operation, emergency contacts, response times)
• Ensure guests know exactly how to reach you — via text, phone, email, or a guest app
• Provide easy-to-find contact info inside the home, such as refridgerator magnets, table tent cards, and printed welcome guides
• Be proactive: a quick mid-stay message asking if everything is going well can prevent issues (and bad reviews)
• Make property information simple to access, including troubleshooting tips
• Respect their space — avoid excessive check-ins or interruptions
• Empower guests with self-service solutions when possible (e.g., FAQs, digital guides)

Stage Seven: Check-Out / Departure 

The check-out and departure stage is the final in-stay interaction your guest will have with your company — and it plays a major role in shaping their final impression. A smooth departure prevents unnecessary frustration, reinforces professionalism, and sets the tone for their post-stay engagement.

Guests are often juggling travel plans, family schedules, and packing during this stage. Clear, simple instructions help reduce stress and ensure they leave the property on time and in good condition. This is also a valuable opportunity to gather feedback, request reviews, and leave them with a positive final touch.

How do your guests check-out? Do they remember what time check-out is? What should they do before they leave the property? These are only a few of the questions you should be asking yourself. Try to think, if you were in their shoes, what questions would you ask when you leave a vacation home.

Objectives & Goals

Your objective in this stage is to make the departure process seamless and easy to understand, creating a positive closing moment to their stay. Your goal is to eliminate unnecessary friction, maintain professionalism, and set the stage for strong post-stay communication.

By the end of this stage, guests should feel:

• Confident about check-out expectations
• Supported if they have last-minute questions
• Appreciative of how simple the process felt
• Open to staying with you again in the future

Key Takeaways & Actions

Here are some of the best ways to elevate the check-out and departure experience:

• Send a clear departure email or text before the guest checks out

• Include essential details, such as check-out time, how to check out (key return, etc.), and if anything should be done before leaving (place dishes in the dishwasher, etc.)

• Keep instructions short, friendly, and easy to follow

• Ensure guests know how to reach you in case they have questions

• Offer a quick opportunity for feedback or a final check-in moment

• Ask for a review while the experience is fresh and top-of-mind

• Keep your tone warm and gracious, reinforcing your brand personality

Stage Eight: Post-Stay & Remembering 

Your guest has checked out, the property is being turned, and their vacation is officially behind them — but your relationship with them is just beginning! The post-stay stage is one of the most powerful phases of the entire guest journey. This is where loyalty is built, repeat bookings are earned, and long-term brand advocates are created.

After all, a guest who has already stayed with you is far more likely to return, recommend you, or leave a positive review… if you stay present in their memory and continue nurturing the relationship.

This stage is also where your broader marketing efforts play an essential role in keeping your property and brand top-of-mind long after their trip ends, including newsletters, social media, and automated follow-ups.

Objectives and Goals

Your objective in this stage is to maintain connection, encourage repeat stays, and keep your brand present in your guests’ long-term travel planning. The overall goal is simple: turn a one-time guest into a lifelong returning guest.

By the end of this stage, guests should feel:

• Appreciated and valued
• Encouraged to return in the future
• Reminded of the positive experience they had with your company
• Confident engaging with your brand on email or social media

Key Takeaways & Actions

First and foremost, when done correctly, nothing converts prospective guests into a booking better than email marketing campaigns. Here are effective ways to strengthen the check-in and arrival experience:

• Send a warm post-stay message thanking them for choosing your company
• Request a review while the experience is still fresh
• Encourage them to share feedback privately if something wasn’t perfect
• Trigger a thoughtful drip campaign, such as booking and stay anniversary emails
• Offer a return-guest promotion or exclusive early-access offer
• Send them newsletters with seasonal updates, local events, travel inspiration, new properties as they become available, and company news
• Invite them to follow you on social media for local tips and updates

Why is the guest experience so important?

A positive experience with a vacation rental company turns into:

• More bookings from 5-star reviews left about your property and a positive reputation online
• Word-of-mouth referrals and a new business promoter
• Another engaged follower on social media
• They may become a return guest in the future, which could guarantee revenue on a regular basis

Final Thoughts

Let’s face it, creating an unforgettable guest experience is one of the most essential tasks vacation rental companies have, and knowing the different stages of the guest’s journey is significant in crafting your unique experience coupled with streamlined processes!

Curious what might help you captivate more travelers in the research phase and cultivate long-lasting guest relationships? Let us help you elevate your guest journey with confidence.

👉 Schedule a call with Cathryn now