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Keystone Award Winners 2021

A rental property management software (RPMS) is the core pillar of any vacation rental software tech stack: it's like the transmission of a car that wires your operation together and makes it go. We chose this year's rental property management software winners because they were:

Most frequently suggested to users of our Proprietary Selector Tool (a tool that matches vacation rental softwares with any given manager's unique needs)

Verified using data from our Current User Feedback Survey (which aims to close the gap between demos of any given software and actual use cases)

Demonstrating upward trajectories (adding new partners, releasing new features & filling "satisfaction gaps" aka. areas where VRM needs are not being met by current vacation rental software market offerings)

Disclaimer: Some of these vacation rental software companies have paid us (to advertise or speak at conferences) in the past but they're not paying us to talk about them right now. We're hyper-conscious of conflict of interest but also believe that our reputation affords us the ability to endorse companies we objectively believe in.  

Mid- to Large-Sized RPMS (50+ Properties)

We begin with what we believe are two of the best all-around vacation rental property management softwares on the planet. No company can do everything perfectly, but these two softwares are challenging that notion with strong development teams and growing partner bases.


Software With No Real Weaknesses

Streamline has the fewest weaknesses of any rental property management software we've researched. If you want as many features as possible and you don't have budgetary restrictions to get the job done, we encourage you to consider Streamline: it's that straightforward. They have a strong new CRM, a hard-working and smart team with dependable customer service, and a robust development arm that continues to improve existing features while adding new ones. Simply a top vacation rental software on the market today.


Superior All-Around Software

Maxxton is a superior all-around vacation rental software that has built a strong following in Europe and is now expanding. Their housekeeping & maintenance module is among the best in the industry, the development team is laser focused and highly capable innovating, and while it is on the higher end of the cost spectrum, if you can afford it, the investment is well worthwhile. This vacation rental software isn't always present in discussions about the best all-around software but it should be. If you haven't already, do a demo with Maxxton -- you'll be impressed.

Next, we move into two vacation rental software disruptors who chose to⚡ zig when everyone was zagging. They are each pursuing their vision and focusing on quality even when it means slowing down or setting limits on growth.


Software of the Future

Track Hospitality Software is what we called the vacation rental software of the future in 2019 and it's living up to expectations. Track's CRM is it's standout feature, allowing you to access your guest's journey from start to finish, then hyper-personalize your re-marketing to those former guests all under one roof. Track has been onboarding new members at record pace, but we also like how they've limited the speed of their growth in order to maintain full quality control (something any VRM can admire).  


A Software That Thinks Differently

Ciirus is extremely under-recognized and we are excited to give it the attention it deserves. A unique combination of power and affordability is its standout value proposition. But most unusual is Ciirus' ambitious in-house development team: their vision to develop in-house modules (instead of depending on third-party software) is a strategic culture you want to grow with. If you haven't heard of them before, do yourself a favor and request a demo: Ciirus' customer service is also very very strong.

Next we recognize several great equalizers who are bringing powerful tech to smaller (yet growing) property managers and owners. Underserved in years past, this demographic (which also makes up a majority of vacation rental professionals worldwide) now has unprecedented access to power.

Small- to Mid-Sized RPMS (less than 100 properties)


Software To Grow With

A second-time winner of a Keystone Award, Hostfully has continued to impress: so few weaknesses and too many strengths to mention, Hostfully brings unprecedented power to owners and managers with less than 100 properties. Hostfully's guidebook module is among the best in the industry, they have super strong distribution model, and a quickly-improving CRM. The team also cherishes relationships with their partners, taking each request, question, and development "personally." Hostfully is a phenomenal software to grow with.


Unprecedented Power

Avantio is a vacation rental software that has a very strong user base in Europe and is expanding. They have a best-in-class website builder (the face of your business), a very strong CRM, and a unique distribution framework in that every integration is direct (ie. no channel manager needed). We really like that Avantio is accepting  pretty much any sized business (down to a few properties) so long as you want to grow. There aren't many vacation rental softwares this powerful willing to work with small companies: a vote of confidence that we think will pay off.


New Kid On The Block

Zeevou is new to the scene and born to disrupt! They have a best-in-class distribution module, which connects directly with a variety of global channels (meaning you don't need a channel manager). Zeevou also has a powerful CRM and can accommodate an impressive range of maturation needs (from 1 property to 1,000). This kind of breadth is very very unusual in a rental management software: if you haven't heard of them, do a demo and see for yourself.

Note: We have strict guidelines for advertising claims. Only approved recipients are given the license to use Keystone Award references in their advertising. Please email matt [at] vrmb.com for licensing requests.

Third-Party (or Ancillary) Software Keystone Winners

This year we are proud to include in our Keystone Awards several companies in the dynamic third-party vacation rental software market: an ever-growing galaxy of specialist tools that plug-into your RPMS in order to perform certain activities extraordinarily well. We've chosen to recognize a few of these companies based on three criteria:

  • Is the company a "fan favorite" mentioned frequently by raving fans in interviews, on forums, and via word-of-mouth? 
  • Does the company's specialty have a direct impact on profit?, direct bookings, cleanliness, safety, and/or reviews?
  • Does the company's category have a "satisfaction gap" in which there is far greater demand than current user satisfaction?

Note: The following third-party tools were NOT subject to our quantitative research process, but rather companies with loyal and vocal partner bases, an important indicator in emerging communities. For anyone wondering, we hope to do a more comprehensive third-party market assessment next year.

Market Data Tools

Not to be confused with dynamic pricing, market data tools like Transparent and KeyData provide information to make better decisions. The biggest difference between these two standout tools is regional popularity (with Transparent popular in Europe and Key Data in North America). Both contribute unprecedented impact on your bottom line. Both can also be used without a RPMS.

Guidebook & Guest Apps

Guidebooks & guest apps are primordial to any guest experience and TouchStay and RueBaRue are two fan favorites that get endorsed regularly (probably because most RPMS guidebook apps aren't sufficient). Both of these companies give guests all the information they need at their fingertips, reducing phone calls and email questions, and curating the destination discovery process in a digestible way. And according to their users, great guidebooks lead to great stays.  

Smart Home Automation

When it comes to smart locks, smart thermostats, HVAC analytics, leak detectors...etc. VRMs appreciate the combo of (a) big company who has the expensive tech part figured out with (b) specialty boutique that understands your niche. PointCentral, an Alarm.com company, cornered this market before anyone else and continues to lead: they are now accepting property managers with less than 5 properties which is a complete game-changer. Most VRMs who do a demo end up becoming partners.


Rental Guardian

Rental Guardian a fan-favorite pushing the boundaries of what it means to offer vacation rental insurance. Damage protection, travel protection, and liability protection, not to mention their new "Master Cancel" program which allows you to offer flexible cancellation terms and still get paid (only available to select PMS at the moment). Vacation rental managers who use Rental Guardian can't say enough positive things about it.


Safely is a different kind of insurance model that vets guests to ensure that no criminals are booking your property, terrorizing your neighborhood, or reflecting poorly on our industry. In today's delicate community climate, where managers must take full accountability for guests, Safely has been recommended over and over again by managers as a company securing that process. We are very keen to see whether this style of guest vetting becomes an industry norm.

Other Tools

Housekeeping & Maintenance

Breezeway is the single software we hear endorsed the most frequently and raving fans are especially meaningful in an emerging sector. Breezeway closes the communication gap in an area most rental property management softwares leave much to be desired (housekeeping and maintenance module). They do it with checklists, photo validation, and a team of nerds who are equally obsessive about the details, safety, and cleanliness of your properties as you are.

Wifi Marketing

This is one of those companies that has buzz: it's frequently recommended by active users as a way to convert Airbnb or Vrbo guests into repeat stays and referrals by asking for email address to access the home's WiFi (not unlike a hotel). If you are looking to grow your contact list and re-market to guests who came from OTAs, this is an exciting new tool towards listing site independence.  

Credit Card Processing

When it comes to credit card processing in the post-covid era, you want a company that is ready to be support you in any chargeback dispute. You need someone who's got your back. Lynnbrook Group is a family company (who doesn't love to support that!) that understands the nuances of our sector. It's recommended by just about everyone who uses them.


We appreciate you visiting the Keystone Awards 2021 and hope our suggestions have been of some value.

Maybe validating something you already knew

Perhaps opening your eyes ? to a new vacation rental software you've never heard of?

Heck, maybe you found a suggestion you disagreed with or a missing category leaving something to be desired

These are all good reactions: we are not full-time vacation rental software analysts, we're just vacation rental nerds looking to better understand the tools that power the independent vacation rental professional to new heights. We always want to improve. We always want to learn. So feel free to email with your personal experience (please no vendor hate mail).

Lastly, the vacation rental software market is one of the most dynamic spaces of differentiation: if you are not at least dabbling in these remarkable innovations, we recommend you do so now: the reward is far greater than the discomfort of new technology.

And remember, it's OK if you don't know what you are doing (that was us at the beginning)! Just tell your software rep up front: ask all the questions and repeat the answers back until you are comfortable: do demos and familiarize yourself with the offerings.  

As with any vacation rental decision, our suggestions should be merely a compliment to the most powerful tool of all (the human brain) in your search to assemble the best solution for your unique needs.

Note: We have strict guidelines for advertising claims. Only approved recipients are given the license to use Keystone Award references in their advertising. Please email matt [at] vrmb.com for licensing requests.

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