Switching PMS Platforms Is Easier Than You Think

Key Takeaways

• Switching your PMS isn’t as hard as it seems — the right platform can make the transition smooth and stress-free.

• Staying with outdated software costs more in the long run through lost time, errors and missed revenue.

• Modern PMS solutions like Hostaway centralize your data, automate repetitive tasks and eliminate the chaos of spreadsheets.

• A future-proof PMS should scale with your business, integrate with major OTAs and offer reliable 24/7 support.

• Investing in a better PMS today sets you up for long-term growth, happier guests and stronger profitability.

Let’s be honest — breaking up with your current PMS can feel overwhelming. Even experienced property managers who know how important the right system is, sometimes stick with outdated software simply because switching seems like too much hassle. The fear of downtime, lost data, the learning curve or a complicated transition can make it tempting to stay where you are — even if your current system is slowing you down.

But here’s the good news: upgrading doesn’t have to be a headache. In fact, the right PMS can streamline your business, save you hours of work and help you maximize your revenue. And with the short-term rental market evolving continuously there’s no better time than now to take the leap.

If you’ve been putting off a change, this might be the perfect opportunity to finally switch to a system that works for you — not against you. Let’s explore why upgrading your PMS is one of the smartest moves you can make and what to look for in your next solution.

Why Switching Feels Hard

Switching your PMS can feel like a massive undertaking. It’s not just about picking a new system — it’s about disrupting the way your business runs, even if only temporarily. There are real challenges to consider: onboarding fees that impact your budget, the time it takes for your team to retrain and the fear that moving all your data could lead to mistakes or lost information. On top of that, if your current PMS is deeply integrated with other tools you rely on, the thought of rebuilding those connections can feel overwhelming.

And then there’s the emotional side of switching. You’ve likely spent years adapting to your current system — learning its quirks, finding workarounds and making it function as best as possible. Even if it’s not perfect, it’s familiar. The idea of starting over can feel like more trouble than it’s worth.

But here’s the bigger question — what’s the real cost of staying with a system that no longer serves you?

Changes in growth and profitability after switching to Hostaway from Guesty.

Why Staying Might Be Harder

While switching to a new PMS comes with short-term challenges, staying with an outdated system can create long-term problems that are much harder to ignore. Many property managers don’t realize just how much their current software is holding them back until they start adding up the hidden costs — lost time, missed revenue and limited growth potential.

Lost time and productivity

A slow or outdated PMS forces you and your team to spend unnecessary hours on manual tasks. Maybe you’re individually updating listings because bulk edits aren’t an option or you’re constantly fixing double bookings that better automation could prevent. What seems like a few extra minutes here and there quickly adds up to hours, days or even weeks wasted over time — time that could be better spent on growing your business.

Revenue leakage

Then there’s revenue leakage. Pricing mistakes, overbookings and inefficient distribution all chip away at your bottom line. Without strong revenue management tools or seamless OTA integrations, you could be leaving money on the table without even realizing it. A more advanced PMS can help optimize pricing strategies, improve booking accuracy and ensure you’re maximizing every revenue opportunity.

Falling behind competitors

The vacation rental industry is evolving fast and technology plays a huge role in success. If your competitors are using a more advanced PMS with better automation, pricing tools and guest communication, they’re operating more efficiently — and gaining an edge over you.

Missed growth opportunities

A good PMS isn’t just about managing your properties — it’s about scaling your business. The right system should help you expand without adding extra stress. If your current software makes it difficult to onboard new properties, connect with new distribution channels or improve guest experiences, you’re missing out on potential growth.

The bottom line?

While switching might feel overwhelming, sticking with an underperforming PMS could be the bigger risk. The cracks often show up in the small, everyday things — lost time, inconsistent data and too many spreadsheets trying to hold everything together.

So, if you’ve been putting off a change, ask yourself: is your PMS helping your business grow, or holding it back?

Migrate Spreadsheets to a Single Database

If you’re still using spreadsheets to track reservations, owner statements or guest details, you’re not alone. Many property managers still rely on spreadsheets to track reservations, owner statements and guest details. It might have worked when you had a few listings, but as your portfolio grows and sales channels increase, it becomes harder to keep up. Data gets scattered, updates fall behind and reports take hours to pull together.

That’s where a modern PMS like Hostaway makes life a lot easier. Instead of juggling endless sheets, you can bring everything into one connected system. All your property, booking and financial data sync automatically across channels, giving you real-time visibility without the manual work.

No more reconciling mismatched versions or chasing down errors. With everything centralized, you get cleaner data, faster insights and more time to focus on growth.

Consolidating your spreadsheets into a single, dynamic database isn’t just a time-saver — it’s a smarter way to run your business.

Why Now is the Best Time to Switch

The short-term rental market isn’t slowing down — if anything, it’s evolving faster than ever. Guest expectations are rising, new technology is reshaping the industry and staying competitive requires more than just keeping up. If you’ve noticed fellow property managers switching to new platforms, it’s not a coincidence. They’re making proactive moves to stay ahead in a market that demands smarter, more efficient tools.

The longer you wait, the harder switching becomes. As your business grows, so do the complexities — more properties to migrate, more staff to train and more custom integrations to rebuild. What might feel like a challenge now could become a much bigger obstacle down the road.

Yes, the upfront cost of switching can seem steep, but the long-term gains far outweigh the short-term effort.

What to Look for: Essential Features of a Future-Proof PMS

Not all property management systems are created equal. If you're considering a switch, it's important to choose a PMS like Hostaway that not only meets your needs today but also supports your long-term growth. Here are the must-have features of a system designed for success:

• Scalability – Whether you manage one property or a thousand, your PMS should scale effortlessly with your business. Look for flexible solutions that grow with you rather than hold you back.

• Seamless OTA connectivity – A PMS  with preferred partner status at major OTAs like Airbnb, Booking.com and Vrbo isn’t just a badge of honor — it means better connectivity, faster data syncing and early access to platform updates that can give you a competitive edge. Hostaway is the only property management system and channel manager to hold the coveted ‘triple crown’ status.

• Robust integration capabilities – No single system can do everything, but a strong PMS should offer a marketplace of integrations and an open API. This flexibility allows you to customize your tech stack, ensuring your business runs exactly how you want it to.

• Reliable customer support – Technical issues and questions will arise — it’s inevitable. That’s why responsive, knowledgeable customer support is non-negotiable. Look for a provider with a proven track record of solving problems quickly and effectively.

Fun fact: Hostaway is the first PMS to introduce 24/7 customer support for short-term rental property managers.

• Comprehensive owner management tools – If you work with property owners, transparency is key. A solid PMS should include trust accounting, financial forecasting and reporting tools that help you maintain strong owner relationships and protect their investments.

• Future-proof development – A PMS is more than just software, it’s a long-term business partner. Choose a provider with a clear development roadmap, a history of delivering on promises and strong market stability to ensure your system evolves alongside the industry.

A forward-thinking PMS isn’t just a tool — it’s a foundation for growth. Investing in the right one now can save you time, increase revenue and position your business for long-term success.

Real-World Success Stories: What Happens When You Finally Switch

If you’re still wondering whether switching your PMS is worth the effort, take a look at how two vacation rental management companies — Park Place Properties and SkyShare Management — turned hesitation into transformation. Their experiences show that while change can feel daunting at first, the payoff in growth, efficiency and guest experience is undeniable.

Park Place Properties, a full-service property management company based in North America, reached a point where its old software simply couldn’t keep up. The team of 32 was struggling to manage 150 listings with outdated software that lacked automation and key features for short-term rental management. As the company entered a major growth phase, it realized it needed a robust all-in-one system that was reliable, offered seamless channel integrations, reduced workload and had a modern user interface (UI) with a minimal learning curve. After reviewing over ten alternatives, Park Place chose Hostaway, for “encompassing everything the others had and more, at a more affordable price”.

The results came fast. Within just six months, Park Place grew its portfolio 180% to manage 420 properties, expanded into 10 new markets and across 10+ OTA platforms, automated multiple workflows and tasks, and improved accuracy. The improvements weren’t confined to just occupancy rates, ADR and guest reviews but even staff morale increased. What made the transition smooth wasn’t just the technology, but Hostaway’s hands-on support. The onboarding team worked closely with Park Place to accommodate their unique business processes and provided an “exceptional and personal” experience. Today, with increased exposure, unified data and advanced automation, Park Place is entering its next stage of growth — to manage 1,000 properties in 15 markets — with Hostaway.

SkyShare Management, meanwhile, started smaller — managing just 22 properties when they decided to modernize their operations. Based in Nashville, Tennessee, their early processes were manual, time-consuming and inefficient, and left little room for growth. Stretched thin, they realized they needed a better way to manage their operations—streamlining processes, automating tasks and being able to scale.

After evaluating multiple solutions, the founders found Hostaway — “as an all-in-one solution that seamlessly managed bookings, pricing, guest communications, financial reporting and maintenance coordination” — to be the clear choice. It’s competitive pricing also made it more cost-effective compared to competitors. Plus, it “had some ‘grit’ — something we really aligned with on a personal level”.

With Hostaway, the company quickly migrated its operations, transforming a daunting experience into an effortless one, and achieving full functionality without major disruptions. As the team learned to harness automation, their efficiency and scalability took off. SkyShare grew from 22 to 140 properties in just three years, achieved an impressive 90% occupancy rate across all properties and realized a client retention rate of 100%. Looking back, the founders’ biggest regret is not adopting Hostaway sooner, as they prepare for their biggest growth year yet with their Hostaway-optimized operations.

Both companies share one key realization: The hardest part of switching wasn’t the process itself, but the decision to start. Once they took the leap, the results spoke for themselves. In both cases, Hostaway’s short-term rental-specific features, intuitive interface, robust API and exceptional onboarding support, turned potential disruption into immediate advantage. They each highlight that modernizing your PMS isn’t about replacing software — it’s about unlocking growth potential that your current system may be quietly holding back.

These case studies make one thing clear: Not making the switch to the right PMS is riskier. Whether you’re managing twenty listings or two hundred, the right property management platform can help you grow faster, work smarter and serve guests better.

Why Hostaway is the Right PMS for You

Not all PMS platforms are created equal, and choosing the right one can transform your business. Hostaway stands out as the industry’s leading all-in-one solution, designed to help you scale efficiently, maximize revenue and streamline operations.

With direct API connections to Airbnb, Vrbo and Booking.com, Hostaway ensures seamless synchronization, reducing double bookings and pricing errors. Our powerful automation tools take the stress out of guest communication, task management and reporting—freeing up your time to focus on growth.

Hostaway’s expansive integration marketplace allows you to customize your tech stack with the best tools for dynamic pricing, guest experience and accounting. Plus, our scalable infrastructure grows with you, whether you manage a handful of properties or a large portfolio.

Hostaway users who made the switch often say the difference is night and day, thanks to powerful automation, 24/7 customer support and a vast network of integration partners that make scaling easier. When you choose a system designed for success, the investment quickly pays off. If you're ready for a PMS that works for you, not against you, now is the time to upgrade.

Taking the Next Step

The right PMS isn’t just about fixing today’s inefficiencies — it’s about setting your business up for long-term success. While transitioning to a new system requires effort, the rewards in efficiency, revenue growth and competitive advantage make it well worth the investment. In an industry that’s evolving rapidly, having the right tools isn’t just an advantage — it’s essential for staying ahead.

This is your opportunity to future-proof your business with technology that helps you scale, streamline operations and maximize profitability. The best time to make that change might just be now. 

Don’t let outdated software hold your business back. Schedule a free demo with Hostaway today and see how effortless switching can be.

Frequently Asked Questions

1. How long does it typically take to switch to a new PMS?

The transition period depends on your portfolio size and how much data needs to be migrated. Smaller property managers can usually complete setup in a few days, while larger portfolios may take a few weeks. The biggest time-saver is choosing a PMS that offers guided onboarding and automated data import tools.

2. Will I lose my existing data when switching PMS platforms?

No, most modern PMS solutions provide secure data migration tools to import your listings, reservations, and guest information. It’s worth backing up your data first, but reliable providers ensure a smooth and loss-free transfer.

3. What should I prepare before starting the switch?

Start by auditing your existing setup: export key data (reservations, guest lists, owner records), note any integrations you rely on, and clean up old or duplicate information. Having this ready makes migration faster and more accurate.

4. Can I keep my current OTA connections during the switch?

Yes, though you’ll need to temporarily pause or relink your listings while the new PMS connects via API. This process is quick, and most systems minimize downtime so you don’t lose visibility or bookings.

5. What signs suggest it’s time to switch PMS platforms?

If you’re spending more time fixing issues than managing properties, relying heavily on spreadsheets, or missing revenue opportunities due to poor automation, it’s probably time. Other red flags include weak support, limited scalability, or integration headaches that slow your growth.