How to Sell a Vacation Rental Business (and Maximize Payout)

You’ve devoted countless hours to building, running, and scaling your vacation rental business.

Now you want to make sure you’re honoring all your hard work, investments, and relationships—by making the best sale possible.

With little information available on how to do it right, it can be hard to know what to pay attention to in this unique process, what buyers want, and where to start, to achieve your optimal outcome.

We’ve created this step-by-step guide on how to sell a vacation rental business to help you throughout the sales process and highlight the ways you can maximize payout.

Build strong relationships with guests AND get a bigger payout—by using a guest communication platform to automate and improve your communications. Supercharge your operation (and valuation) with RueBaRue.

What big buyers are looking for

Buyers of all sizes want proof of business viability—but big buyers also want a healthy number of listings they can acquire to build up their own property portfolio and scale their business.

No matter the buyer, they need their criteria met. Understanding those criteria, and putting yourself in the mind of the buyer, will help you better meet their needs and make the sale.

Possible big buyer criteria include:

  1. The number of units: According to Airbnb rental mogul Julie George, having a vacation rental business with 10+ units puts you in direct sight of big names in the business looking to scale. The bigger your portfolio, the bigger, hungrier fish you’ll attract.

Automated messaging

Automate your email and guest text messaging and cut your guest communications in half. SMS and email automation tools save you from fielding repeat questions from guests before, during, and after their stay.

There are a number of software solutions out there with useful tools and features to keep your inbox under control.

Effective features to look out for:

  • Auto-send and auto-respond tools
  • Message scheduler
  • Message templates
  • Macros
  • PMS integration
  • Unified inbox

RueBaRue’s message scheduler helps to cut down guest messaging by up to 70%. Source: RueBaRue

Automating your guest messaging is easy to set up and saves you tons of time, making it a must-have business hack.

Digital guestbooks

Welcome books offer a wealth of information, answering most guest questions about the Wi-Fi or local attractions upfront before they get a chance to ask you.

They also provide massive branding opportunities, helping you to capture more short-term rental owners and in turn, expand your portfolio.

In addition to all this, digital guestbooks in particular save you running from property to property replacing dog-eared, outdated paper copies, and are undeniably better for the environment.

Useful features you should be looking for are:

  • Master guide templates
  • Search algorithm-generated local area guides
  • PMS integration
  • Automatic, scheduled delivery
  • Customizable logos and colors
  • Mobile and desktop friendly

Optimize your digital guidebooks by automating and score yourself a win-win. Guests get the most out of their stay, and you reduce their questions.

You also increase the probability of repeat bookings and stand out to property owners, making them as valuable for guests as they are for property managers.

Review generation

More 5-star guest reviews are the key to standing out in OTAs and driving bookings. Simply relying on guests to post reviews means you’re missing out on free publicity, but constantly chasing them up eats into time better spent elsewhere.

We suggest asking guests to rate their stay using automated review requests. The automation software sends a text message that arrives an hour after checkout, leaving them no excuse.

And you can save even more time by finding a software solution that offers text or email templates that you can customize as needed. Another automation tool at your disposal is scheduling a follow-up message that contains a link for posting a Google review or a survey about their stay.

As an example of this at work, RueBaRue has an invaluable scheduler tool that sends an automated message for the morning after check-in to catch any potential issues. If there are any, respond to them immediately and improve the likelihood of a positive review.

Capitalize on RueBaRue’s post-arrival message scheduler and multiply your 5-star reviews. Source: RueBaRue

Automate with RueBaRue and instantly reduce your time spent on guest communications by up to 70%. Schedule a 30-minute demo.

Calendar management

Juggling so many properties means that calendar management is likely yet another demand on your time.

But with automated integration software in place you can streamline your vacation rental business.

PMS integrations

Once your property management business reaches a certain size, you'll find yourself using multiple booking channels, but this soon gets tricky, and simply isn’t sustainable for a growing business, which is why you’ll need a solution once you reach three to five properties.

Integrating all your different OTA calendars with a PMS means you can see all your bookings, on all channels, in the same place. This is more time-efficient and reduces discrepancies between different calendars.

We recommend a PMS or channel manager that offers the following features and benefits:

  • Automatic application of changes across all your OTAs
  • Blocking off of specific periods simultaneously
  • Rate changes that apply to all channels
  • Lower rate of double bookings
  • Vacancy reduction

Google calendar

For a cheaper multi-calendar view, export your vacation rental calendars to Google Calendar.

Do this by getting your iCal link and adding it to Google Calendar via the “Add calendar” option and clicking “From URL”. This way bookings from all your platforms will automatically sync with Google Calendar. You can even add external bookings too.

The downside is that it doesn’t sync bookings right away, taking up to as much as 24 hours to update. Nevertheless, if you’re managing more than 10 properties, a dedicated PMS is a prerequisite.

Self check-in

Managing keys, driving to properties, waiting around for guests to arrive, and struggling through small talk. Just thinking about check-in is enough to elicit groans.

Automating the process via contactless check-in is the perfect time-saving solution. It's also a massive benefit for the guest as they no longer need to rely on someone to be there to let them in. This way you’re reducing your workload and improving the guest experience.

Here are the three main ways to go about it.

Keyless locks

Keyless locks, such as those provided by Schlage and August, are one of the most convenient and safe self check-in methods. They come in two forms—keypad and smart touch.

You install a keypad lock by fitting an electronic keypad to the property entrance and guests access the property by entering a temporary security code on the keypad.

Smart touch locks work similarly but are set up and opened using a smart device (for example a smartphone). Using their device, guests can enter the property and you even get automated notifications tracking guests’ comings and goings.

Smart lock being used during the check-in process. Source: Unsplash

Key exchange

Key exchange systems are another innovative and cost-effective way to allow self check-in.

To use a service like KeyNest all you need to do is drop off the keys to the property at a nearby store. Then give the guest the provided collection code and they use it to pick up the keys on arrival.

Keycafe offers a similar service. But instead of the guest collecting the keys from store workers they collect them from a SmartBox inside the store. As it’s a fully automated system this allows for real-time updates and tracking.

Another option is EveryDoor. They provide guests access to the property by making a phone call or inputting a security code. Once inside, they find the keys wherever you stored them on the property.


Lockboxes are key safes, designed as a secure way to store the keys outside the property. They are strong but discreet and only need guests to key in a unique pin code.

There are several lockbox systems with varying lock designs such as a wheel, push-button, dial, and electronic or smart locks. So, make sure to pick the solution that best suits your needs.

Automated cleaning software

The bigger the portfolio, the bigger and more disparate the team you need to manage. Nothing is worse than when reservations miss a booking, maintenance forgets a crucial job, or the cleaning staff misses a check-out.

It’s a lot to keep on top of but take advantage of the following automation tools to simplify your property management.

Automated cleaning software

Constantly messaging or calling to schedule cleaning eats up a lot of your time. We suggest you automate this busy work instead with the following software solutions.

Cleaning automation tools that integrate with your PMS include TurnoverBnB, Properly, and Breezeway.

Add your cleaning staff, and their respective properties, to the software. Then your vacation rental management software will automatically update the cleaning app with a new task as needed.

This simple tool automates scheduling and tracks tasks for you, making sure your team is on top of things. You save time and improve the guest experience in the process.

Google Calendar

For a free alternative use Google Calendar to automate your team scheduling.

Again, all you need to do is get the iCal link from your OTA and add it to Google Calendar.

Share your calendar with cleaners, maintenance workers, and other team members so they see what tasks they need to do and when. They can even add the iCal link directly to their personal Google Calendar.

This still requires manually updating the calendar and remember, it only syncs once every 24 hours so staff are less likely to pick up on 11th-hour changes.

This makes the low-cost investment in a dedicated software solution a more time-efficient and sustainable choice.

Real-time workflow automation

Tools like Zapier automate messaging and alerts to your team and external contractors. Although it takes a little bit of getting used to at first, you soon see the benefits.

Zapier integrates with both your PMS and your messaging and team collaboration apps, automating messages by using a system of triggers and actions.

For example, if a guest changes their check-out date this could be a trigger. Zapier then automatically sends a message to the cleaning staff to let them know (the action).

This tool also cuts down on task oversight as jobs won't get lost in the shuffle or forgotten about.


Accounting and payroll are a time-consuming, never-ending, and headache-inducing process. And finding a qualified accountant, not to mention the accompanying costs, is daunting.

Let the following software solutions cut your paper trail to shreds.

Dramatically reduce your paperwork and automate your payroll. Source: Unsplash

PMS and accounting software integration

Forget keeping track of many, ever-changing spreadsheets. Use PMS integrating services such as QuickBooks and TallyPrime, and automate payroll.

Enter the relevant employee and business details into the system and these tools calculate, file, and pay your payroll taxes for you. They offer same-day direct deposits which means you keep hold of cash longer and pay your team on your schedule.

This is a great way to cut back on time spent by the calculator. This leaves you more time to focus on the long-term goal of growing your business.

Accounts payable automation

A growing property portfolio means a growing list of accounts payable and a longer paper trail. Laundry services, pool cleaning, one-off maintenance jobs, and the list goes on. Use AP automation tools such as PaperSave or to speed up invoice processing.

Common functionality and perks:

  • Automated invoice data extraction
  • Invoice matching
  • Automated invoice approval
  • Cut back on human errors
  • Reduce double payments

Dynamic pricing

So, you’re on top of seasonal changes in demand, you know when local events are taking place and you’ve set your rates accordingly.

But now you’ve got to apply those rates across all channels. And let’s face it, there are much better uses of your time than copy-pasting for hours.

Get rid of the hassle and simplify your pricing with the following software solutions.

Dynamic pricing tools

Use a dynamic pricing tool such as Wheelhouse, PriceLabs, or Beyond Pricing. They automatically adjust your rate on a nightly basis by monitoring what’s going on in the market.

These tools use AI, historical information, and real-time market data, which helps you sidestep under or over-charging on your rates.

Dynamic pricing cuts down time spent on market research and boosts bookings. You can even improve individual property performance.

Airbnb Smart Pricing

For a cheaper alternative, Airbnb offers its own dynamic pricing automation system. It's called Smart Pricing and comes integrated within Airbnb’s calendar, automatically changing the price of your property based on the demand for similar listings.

To activate Smart Pricing first click on the “Nightly pricing” option. Next, choose a minimum and maximum price and customize the tool by manually adjusting nightly rates as needed.

Breathe easy with vacation rental automation

As your vacation rental business grows it can be an exciting time. But this excitement is often offset by the daily struggle to stay on top of your to-do list.

Guest communication is high on that list, so automate it with tools like RueBaRue. Our solution to guest messaging provides the best bang for your buck because it’s:

  • Easy to implement
  • Cost-effective
  • Time-efficient
  • Comprehensive, with a huge range of features, including Digital Guestbooks, Extend Guest Stays, and Guest Reviews

It provides a better guest experience and makes your services more attractive to property owners.

Ease the stresses involved in an expanding portfolio and bring back the feeling of stability and optimism you’re looking for. Automate and give yourself the time and space you need to focus on the future of your business.

Reduce guest communications overnight with RueBaRue and watch your property go from strength to strength. Schedule a 30-minute demo.

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