How to Choose a Vacation Rental Software? Ask Yourself These Questions


As the vacation rental industry grows, so do the number of products and services available to owners, managers, and agencies. Searching for, evaluating, and adopting these tools and technologies can be a cumbersome and time-consuming process.

And yet, one of the biggest decisions for your vacation rental business is choosing one such tool in particular: a vacation rental management system.  

High-level, vacation rental management software should save you time and help you generate more bookings. On a more basic level, it should do what you want it to do.

So I ask: what is it that you want your vacation rental management system to do?

Before choosing any software, it’s important to have clear the answer to this question.

Thus, below I pose a host of questions for you to consider– divided into five sections including Calendar Syncing, Channel Management, Pricing & Revenue Management, CRM System Functionality, and Company Ethos.

1. Calendar Syncing

  • What kind of synchronization are you looking for exactly?
  • Are you looking to synchronize using iCal? If so, then are you therefore OKAY with a 6-8 hour delay for your updates to be pushed?
  • Or would you rather have something more instant?
  • Should this synchronization work with your website as well? In this case, do you have widgets or an API in order to connect your website with the given software in the style and user experience you’re looking for?

2. Channel Management (Airbnb, VRBO,, etc.)

As far as channel management goes, it’s essential to ask what level of integration you want as there are almost as many ways to integrate as there are softwares out there. Questions like:

  • Do you support 2-way synchronization with [portal/channel goes here]?
  • What property details (e.g., dates, rates, property description, amenities, photos, special offers, etc.) are distributed and synchronized?
  • What time lapse do you have for a new update to be pushed or retrieved?
  • If you’re able to synchronize rates, how do you synchronize more complex pricing schemas required by vacation rentals managers and not supported by some of these portals?
  • How do you synchronize fees and taxes?

Note that some portals support only a single tax. But, in Canada, for instance, there are 3 types— Tourist tax, GST, QST (at least in Montreal).

  • How do you handle payments? What payment gateways do you support?

3. Pricing & Revenue Management

  • Do you support [all your pricing logic goes here: last minute offers, early bookings, long stay discounts, weekend increases, etc.]?
  • Do you support specific periods of time?
  • Do you have an API (free and public) or partnership with a pricing optimization company?

4) CRM System Functionality

  • Can you export to emailing systems?
  • How much or how little information can you track per customer? Is this information sufficient for your invoicing, targeted marketing, and other needs?

5) Company Ethos

I would also recommend looking for a few more details:

  • How open or closed is the ecosystem of the software being evaluated?

An open system with complete and modern APIs will let you extend functionality if you ever need to, say, due to growth or other business demands. Further, you’re able to access all your data at any time in a structured manner, which makes it easy for you to leave and switch softwares if you’re no longer happy. You should always have easy access to your data and never be stuck.

  • Who owns and runs this company?
  • What is the company’s goal? vision? If it is to grow quickly and cash-out fast, would an acquisition leave your VR business in danger should the new buyer pivot?
  • Do you share the same beliefs and feel comfortable having this company as part of your business?

In my opinion, your vacation rental software will become a member of your team. It’s a key component to your business and you should feel comfortable with its soul.

I’ll finish with a quick saying that I believe is right to the point:

We say in real estate the three most important factors are:

  1. The location
  2. The location
  3. The location

In software these three key points are:

  1. The team
  2. The team
  3. The team