scale rentals conference barcelona

How to evaluate vacation rental software, with Keystone Awards’ Terry Whyte

How to evaluate vacation rental software, with Keystone Awards' Terry Whyte

Sometimes it might feel like there’s a new vacation rental software out there every day, and let’s be real, this is not so far off from the truth. As of today, G2 lists a whopping 349 different property management software. Choosing from this smorgasbord can be quite a challenge, but Keystone Awards’ Terry Whyte has got it down to a science.

Known befittingly in the industry as ‘the vacation rental software guy,’ Terry has cultivated this reputation through years of critical analysis of vacation rental software. After years of live demos and parsing vacation rental tech products for strengths and inadequacies, Terry co-founded the Keystone Awards with Matt Landau of the Vacation Rental Marketing Blog to acknowledge standouts in the sector.

Some Keystone Awards 2021 winners include Transparent, Hostfully, Avantio, Breezeway, and StayFi.

Banking on data to find the best vacation rental software

how to choose the best property management software

In the Keystone Awards, Terry combines his 30-point benchmarking strategy developed over thousands of PMS demos hours with user feedback and public reviews to recognize proponents of groundbreaking technology within the vacation rental industry. Typically, property management systems take up a sizable chunk of this recognition, but the 2021 Keystone Awards will also consider ancillary tools that making waves in their own right.

What should property managers and owners look for in vacation rental software?

In this deeply revealing interview, we further explore what went into creating the ranking system used in the Keystone Awards today. We also discover answers to many important questions:

  • What, if anything, sets bigger players apart from the relatively smaller ones when it comes to creating effective property management software?
  • What should you, as a property owner or manager, be on the lookout to find the best possible PMS suited for your business’s unique needs?
  • What are the top PMS vendors getting right that emerging vendors could learn from?
  • What is a common mistake PMS vendors continue to make that can cost them their longevity?

In addition to this, he also briefly discusses what vacation rental software vendors are doing wrong when it comes to demos.

Terry and Matt Landau have also put together a remarkable resource for vacation rental companies struggling with building a tech stack. The Agile Approach: How To Build The Ultimate VR Tech Stack is a cheat-sheet for those looking to quickly and efficiently find software that works for their specific needs and skip the trial-and-error that plagues those on the lookout.



Uvika is a Content Editor at Rental Scale-Up. She uses her experience as a digital nomad and a social media expert to reveal and share vacation rental industry trends.


Table of Contents

Dear Short-Term Rental Industry Member, Join Our Scalers Network

Our Mission

We bring together short-term rental industry members to create valuable business and personal relationships. With the support of vetted peers, you can deliver on your next individual project goals faster, work in private groups to share doubts and successes, and become a new voice that shapes the conversation about our industry.

Whether you are a property manager, an owner, an industry vendor, a listing site operator, an investor, or a consultant, you can become a member of our Rental Scale-Up family.  As property managers and industry vendors may not have the same needs, some of our activities work by affinity groups. For instance, we have one version of the mastermind group sessions reserved for property managers and owners, and another one for vendors and listing sites. This way, you get feedback from peers who understand your pains and can get you faster to getting results.

1. Action, Transformation & Results

  • Mastermind Group for Property Managers & Owners: A mastermind group is a group of peers who meet to give each other advice and support. Facilitated by Rental Scale-Up. One session every 2 weeks with your group for a least 3 months.
  • Ask a Property Manager: Hosts, owners and property managers benefit from the experience of a successful property manager. (1 per month)
  • Groupwork: Report of the month co-creationA group of Scalers volunteer to write a report on the topic of the month. The result is published on RentalScaleUp.com, with full credits to each participants. (1 per month)
  • Mastermind Group for Industry Vendors & Listing Site Operators: A mastermind group is a group of peers who meet to give each other advice and support. Facilitated by Rental Scale-Up. One session every 2 weeks with your group for a least 3 months.
  • Ask an Expert Anything (for vendors and listing sites): An outside expert (e.g. a copywriter) shares their experience on a topic in an Ask Me Anything (1 per month)

2. News & Live Discussions

  • Investment & Deals  Discussion: Thibault and an M&A specialist/VC go over recent deals, M&A, investment rounds. Live, monthly.
  • Curated news: Save time. We read the news for you, curate the articles, and add our exclusive comments (weekly, in the Network Newsletter)
  • US Trends & Data Discussion: We analyze AirDNA’s latest report on US trends and zoom in on key markets (e.g. urban vs vacation rental markets).  Network members share what they see in the markets. Live, monthly.
  • Monthly Live online conference: Every month, our Network deep dives into a topic that is crucial to the short-term rental industry. 3 experts share their insights, best practices and answer your questions live.
  • European Trends & Data Discussion: We analyze AirDNA’s latest report on European trends and zoom in on key markets (e.g. UK, France, Italy, Spain).  Network members share what they see in the markets. Live, monthly.
  • Weekly Teardown with Thibault: Rental Scale-Up founder tears down one business news, every week, live.  Networker members share their views. No filter.

3. Facilitated Networking

  • Networking Booster: Meet new business partners and improve your networking game at an online event. Our team facilitates the event to make it easy for you to connect with your peers. (monthly)
  • Business Profile: Each new Scaler gets their profile featured in a dedicated article on RentalScaleUp.com. Get more visibility and authority.
  • In-Person Meetups: We meet in real life, either during a large vacation rental conference or in a city of our choice (quarterly)
  • Job Offers: Network members can not only see job offers but also post theirs. If desired, job offers can be extended to all Rental Scale-Up readers (free and paid).

4. Deals on industry software and products

  • Get Discounts: Enjoy exclusive deals brought to you by fellow Network members. Only in our Deals section. Monthly.
  • Offer Deals and Discounts: Network members may offer exclusive deals to fellow members, from discounts on stays at their properties to lifetime deals on vacation rental software. Only in our Deals section. Monthly.

Ready to join right now?

Scalers comes in 3 levels:

  • Scalers Insights, the limited, content-only version of the network. Great those who just want to get the insights but have less time for business transformation.
  • Scalers Network: Transform your business and get results. Get more things done. You get support, accountability, networking, training, and investment opportunities
  • Scalers Network+ : Avoid the hassle of quarterly payments and pick an annual membership. Qualify for bonuses good for your business (e.g. lead generation)

Not quite ready? Sign up for our free newsletter

Weekly insights straight into your email inbox.

On Key

Related Posts

airbnb 2022 summer release update

Airbnb 2022 Summer update release

On May 11, Airbnb will release its 2022 Summer update. Here’s what we can expect from it, as hinted by Brian Chesky, the company’s CEO and guessed by our Rental

Actionable insights

Take the Right Decisions for Your Rental Business thanks to our Weekly Industry Brief.

Exclusive newsletter for rental entrepreneurs.