A Journey Through 11 Property Management Software Options In Our Quest For Perfection

When we decided to scale up our property management operations at Homevy, we knew we needed a robust Property Management System (PMS) to handle the growing complexity. Little did we know that finding the right software would turn into a weeks-long adventure filled with demos, disappointments, and unexpected discoveries.

Here’s our story of how we went through different options and why we ultimately chose Hostaway.

Chapter 1 – The Great Property Management Software Hunt Begins

Picture this: our team huddled around a whiteboard, actually we didn’t use whiteboard, it was a notion thread :).

We listed all the features we dreamed of having in a perfect software. The list kept growing until it resembled a software engineer’s dream:

• Actionable guest profiles / CRM
• Bulk messaging & marketing automation
• Automated smart messaging
• Unified Inbox
• Guest reviews management
• Smooth UX and impressive UI Design
• Mobile-optimised e.g Mobile app
• Customer support & response time
• Key management automation
• Calendar synchronization
• Revenue management
• Maintenance management
• Cleaning management
• API provision & API capabilities
• Availability of booking engine & sample
• Official Airbnb partnership
• Third-party integrations
• Guest FAQs management
• Impressive analytics
• Accounting integration and hosts statements
• Security
• Payment processing
• Owners portal

“How hard could it be to find something that checks all these boxes?” we naively wondered. Spoiler alert: very hard.

Chapter 2 – First Stops: Let’s Visit The Popular Options

Our journey began with the big names everyone recommended. Guesty was our first demo, and it certainly made an impression with its comprehensive feature set and polished interface. The sales representative was good, and he guided us through a great demonstration that showcased powerful automation tools and an impressive unified inbox.

“This could be the one!” we thought, until we saw the price tag. For a growing company like ours, the investment was significant. We decided to keep our options open.

What made it even more challenging was that Guesty was actually a close call for us. We were seriously considering it despite the cost, but what ultimately pushed us away was the poor sales support after the demo. The representative made us feel like we were begging them to use their software, which left a sour taste. When you’re making such a significant investment, you expect to be treated like a valued partner, not an inconvenience. We decided to keep our options open.

Next came Hostfully, which impressed us with its intuitive design and strong focus on guest experience. And their digital guidebook was tempting. But something about it didn’t quite align with our operational workflow. We took notes and moved on.

Chapter 3 – Middle of the Pack: Surprises and Disappointments

The demos started blending together as we explored Lodgify, iGMS, Hospitable, and more. Each had its strengths:

• Uplisting won points for its sleek booking engine
• Avantio impressed with its channel management
• Doorloop had strong accounting features
• Hostify offered great messaging automation
• Hosthub had some interesting automation tools, but lacked the depth we needed

But none felt like the perfect fit. Some lacked mobile capabilities, others had clunky interfaces, and a few were missing critical integrations we needed.

By the time we reached demo number seven, our team had developed a sixth sense for PMS strengths and weaknesses. We could spot a weak calendar sync feature within minutes or identify a powerful automation tool in seconds.

Chapter 4 – The Unexpected Contender: Hostaway Enters the Scene

When Hostaway appeared on our schedule, we didn’t have particularly high expectations. It wasn’t the most talked-about option in our industry circles, but we were committed to being thorough.

The demo started, and immediately something felt different. The interface was clean without being simplistic. The calendar management seemed intuitive yet powerful. The channel management capabilities were comprehensive without being overwhelming.

Our operations team perked up when they saw how tasks could be assigned and tracked. Our guest relations team loved the unified inbox. Our finance department nodded approvingly at the reporting capabilities.

“This might actually work for us,” we whispered to each other as the presentation continued.

Chapter 5 – Decision Time: Why Hostaway Won

Photo by nappy

After eleven demos and countless hours of discussion, we created a comparison matrix. Hostaway rose to the top for several key reasons:

1. Balance of features and usability: While some systems offered more bells and whistles, Hostaway provided everything we needed without overwhelming complexity.
2. Pricing structure: It offered a competitive price point that scaled reasonably with our growth plans.
3. Mobile functionality: The mobile app meant our team could manage properties effectively while on location.
4. Channel integration: The system connected smoothly with all the major booking platforms we used.
5. Customisation options: We could adapt the system to fit our specific workflows rather than changing our processes to fit the software.

After a final team vote, we made our decision: Hostaway would be Homevy’s new property management system.

Chapter 6 – The Honeymoon Phase and Reality Check

Implementation went relatively smoothly. Our properties were imported, our team was trained, and we started enjoying the benefits of automation and centralised management. For the first few weeks, it felt like we’d found our perfect match.

Then reality set in.

No software is perfect, and Hostaway had its share of issues that only became apparent with daily use:

• Owner dashboard limitations: What looked comprehensive in the demo turned out to be less intuitive for our property owners. Many reported difficulty finding the information they needed. The owner dashboard was packed with too many things that an owner couldn’t care less about. And… it comes Hostaway-branded, like Hostaway is the property manager rather than Homevy. This pushed us to build an owner dashboard in-house.
• API documentation challenges: Our tech team struggled with the API documentation, which was often vague or outdated. For instance, the finance calculated report endpoint has an extra dateType of “Calendar”, which was nowhere to be found in the documentation. We had to figure it out another way, because the technical support team takes days to respond. Also, implementing custom features took much longer than anticipated.
• Channel synchronisation challenges: Importing and exporting data to booking channels sometimes felt like shooting in the dark. Would the changes appear immediately? In an hour? Would they appear at all? It became a regular guessing game. If anything goes wrong with our export, you have no idea what went wrong.
• Slow customer support: Perhaps the most frustrating issue is the response time from customer support. Simple questions can sometimes take days to receive answers.

The other day, our technical team opened a support request regarding coupon code not working, Hostaway’s Technical Support Manager replied after one day, he/she then passed it on to someone from the technical support team, who also replied after an extra one day, then also passed it on to their internal API team, and then we just had to go play some padel tennis while you hope for the best to get a response soon.

Chapter 7 – Lessons Learned and Moving Forward

Despite these challenges, we don’t regret our choice. Hostaway remains a good fit for our specific needs among all the options we evaluated. The imperfections remind us of an important truth: there is no perfect PMS solution in the market. Each option involves trade-offs.

For companies embarking on their own PMS search, we offer these hard-earned tips:

• Look beyond the demo: Ask detailed questions about the features that matter most to your specific operations.
• Talk to current users: Seek out companies similar to yours who are using the system and ask about their real-world experience.
• Prioritise your must-haves: Every system will have shortcomings. Know which features you absolutely cannot compromise on.
• Consider growth plans: Choose a system that can scale with your business without becoming prohibitively expensive.
• Plan for imperfection: Budget time and resources for workarounds and customisations you’ll inevitably need.

The End – The Journey Continues

Our PMS journey didn’t end with implementation. We continue to discover new features, develop workarounds for limitations, and push for improvements through feature requests.

The search for the perfect property management system is perhaps a never-ending quest. Technology evolves, business needs change, and new options emerge. But for now, Hostaway serves as our imperfect ally in property management – helping us grow despite its occasional frustrations.

And isn’t that a bit like any worthwhile relationship? Finding something that works well enough for now, while always looking for ways to make it better.

If you’re currently drowning in PMS demos and feature comparisons, take heart. The perfect solution may not exist, but the right-fit solution for your business is out there. And sometimes, discovering its quirks and limitations is just part of the journey toward operational excellence.