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Unlock Revenue in Your Guest Journey: Strategies to Expand Without Extra Work

Building a scalable and profitable vacation rental business requires focusing on the opportunities within your guest journey. While expanding the number of rental properties can increase revenue, it also demands more resources. Alternatively, you can optimize your existing properties to generate more rental income. How can you achieve this? This guide presents actionable steps to unlock revenue in your vacation rental guest journey. We will explore how to offer upsells more proactively and increase conversion rates.

"The question is, how do I continue to grow without necessarily creating more work for myself? And that's where Enso Connect really answered this question."

Mark BiesackCEO & Founder of PowerHouse Properties

Watch the full case study.

The Guest Journey

Let’s review the steps of the guest journey that offer revenue opportunities for short-term rental businesses.

The Vacation Rental Guest Journey

The Concept of Touchpoint, Schedule, and Medium

Direct-to-consumer (DTC) platforms like Uber have built solid user journeys by leveraging digitization, data, and personalization at scale. It requires a savvy mix of data collection, scheduling, and the right medium to provide a seamless user experience.

Simply put, why should a person engage with your brand? And how, when and how frequent to communicate your offer to drive engagement and conversion?

Touchpoint: When should you communicate or perform a task?

Schedule: How frequently should you communicate or perform the task?

Medium: What channel will you use to communicate with guests?

Touchpoints, schedule, medium concept

Understanding Your Guest: What Do You Need to Know? 

Understanding your guest is crucial for maximizing revenue and enhancing their experience. You need to know their preferences, expectations, and pain points at every stage of their journey. From the initial inquiry to post-stay follow-ups, each interaction offers insights into what your guests value most. Quick responses, clear booking confirmations, secure verification, seamless check-ins, and personalized in-stay communications all contribute to a positive guest experience. By leveraging this knowledge, you can tailor your offerings, anticipate needs, and provide exceptional service. This will drive guest satisfaction and loyalty.

What do you need to know about your guest?


Why: This is your chance to sell; the guest is shopping around and inquiring about information.

Problem: If you don’t respond quickly or follow up, potential guests will move on to competitors.

Touchpoint: Reply immediately after the inquiry. If the booking doesn’t occur after the first interaction, follow up within an hour.

Schedule: Your guest service team should manage inquiries and schedule automated follow-ups to increase conversion rates.

Medium: Use the channel the prospect contacted you on, whether OTA or your direct booking website.

Booking Confirmation

Why: Instill confidence in your guests regarding payment processing, dates, location, and overall experience.

Problem: Delays in addressing concerns can cause frustration and negative reviews.

Touchpoint: Anticipate guest questions by providing automated confirmation messages and guides for packing and getting to the property. Upsell transportation or parking services.

Schedule: Confirm bookings automatically via messages and provide ongoing communication through a guest portal.

Medium: Use a guest portal like Enso Connect’s Boarding Pass for all guest needs throughout their stay.

Guest Verification

Why: Reassure guests about the security of their personal information and collect data for personalized service.

Problem: Asking for ID via text can seem unprofessional and unsafe.

Touchpoint: Send verification requests well in advance, about 1-2 weeks before check-in.

Schedule: Remind guests to complete verification and confirm once done.

Medium: Use secure, user-friendly forms and document upload options for sharing personal information.

SMS: Medium for Guest Verification


Why: The first guest experience sets the tone for the stay.

Problem: Vacation rental check-ins lack the certainty of hotel check-ins.

Touchpoint: Send check-in instructions a few days prior. Many hosts use smart lock integrations for unique door codes.

Schedule: Verified guests receive check-in instructions in due time.

Medium: Provide a single place for check-in instructions and lock codes, like Enso Connect’s Boarding Pass.

During Stay

Why: Guests are receptive to enhancements during their stay.

Problem: Guests on vacation don’t read lengthy emails.

Touchpoint: Timing is crucial. Provide Wi-Fi info and amenity guides upon arrival. Time upsell offers appropriately.

Schedule: Use automated and ad hoc messages for guest engagement.

Medium: A guest portal is ideal for property and neighborhood guides. Include upsells for a great e-commerce experience, like with Boarding Pass V3.


Why: Checkout is an opportunity for upsells and requesting feedback.

Problem: Automated review requests can lead to negative reviews.

Touchpoint: Send a checkout reminder 16-24 hours before the scheduled time.

Schedule: Provide checkout instructions and monitor guest satisfaction through the app and AI analysis.

Medium: Include a link to the guest app in the checkout reminder for instructions, upsell offers, and review requests. Add a direct booking website and social media icons to encourage future bookings with Enso Connect.

Post Stay

Why: The post-stay stage allows operators to maintain engagement with guests. It encourages guests to return for future stays or recommend the property to others.

Problem: Losing connection with guests after departure can lead to missed opportunities for loyalty and re-booking.

Touchpoint: 24-48 hours after checked out, send guests a message thanking them for staying at your property. Ask for feedback/review, invite to book with you again.

Schedule: Guests data collected through all the touchpoints is leveraged to tailor communication and retargeting strategies

Medium: Email and WhatsApp campaigns are the best medium for customer re-engagement promotions.

Unlock More Revenue With Less Effort

Implementing a strategic guest journey optimization plan allows you to maximize revenue from existing rental properties before expanding your portfolio. Tools like guest portals, messaging inboxes and comprehensive guest experience platforms can streamline operations too. With the right approach, you can elevate your vacation rental revenue without the added work of more rental properties.

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