It’s no secret that running a successful vacation rental business takes time, effort, and money. Savvy property managers know that having the right vacation rental software can alter the course of their business—for better or worse.
With so many options available, choosing the right property management system can feel overwhelming. Breaking your evaluation of a PMS down into categories can help you get a clearer picture of your options (and maybe even reveal a clear winner).
Take stock of where you are (and where you want to be)
The foundation for a successful transition lies in thorough preparation. Lay the groundwork for a solid switch by assessing your company’s unique needs and long-term goals, considering factors like the number of units you manage, the size of your team, and the specific pain points you want to address. This also includes mapping out your company’s workflows, ensuring all stakeholders are aligned, and understanding how the ideal system will fit your business needs.
Features and Pricing
A good rule of thumb is to choose a PMS with features that handle tasks you dread or that would take too long to figure out yourself. Trust accounting features, for example, simplify financial statements and ensure accuracy, while AI-powered guest engagement and advanced revenue optimization help you make smarter booking decisions.
Another crucial consideration is whether a PMS is all-inclusive or uses an à la carte model. Some systems come with only the basics and require you to purchase add-ons to access more complex—but often critical—features.
With the dynamic nature of the short-term rental industry, you may findyourself in need of additional tools down the road. Relying on less feature-rich à la carte options like Guesty makes you more vulnerable to pricing changes and could unexpectedly leave you reliant on costly add-ons. Streamline, however, is all-inclusive—so you never have to tack on another line item just to get the tools you need.
Integrations
While your PMS is the foundation of your operations, it’s likely not the only asset you use. When evaluating a PMS, you’ll also want to make sure it has a robust offering of integrations. These should include booking channels, guest experience services, and a variety of other solutions that can help boost your business. It’s important that the tools you rely on can “play nice” with one another, so a wide offering of integrations helps ensure smooth sailing.
In addition to making your day-to-day a little easier, integrations are good for business. Having vacation rental software that integrates with OTAs and distribution channels can exponentially increase the number of people who view your rentals. Streamline’s VRBO Elite Connectivity Partner status shows how well it works with top industry vendors.
Customization & Scalability
No two property management companies are exactly alike, so the ability to customize your new software is crucial. Tailoring features like pricing, booking channels, and guest communication to your needs ensures the system works seamlessly with your business operations.
Scalability matters just as much as customization. Unfortunately, some property managers invest in a system that just can’t keep up. When they inevitably outgrow it, they’re forced to start over, repeating the very hassle they hoped to avoid.
With 2,000+ variable configurations, Streamline flexes to your business model today and grows with you tomorrow—ensuring you never have to “break up” with your software again.
Support & Training
Learning a new technology can present challenges for anyone, especially property managers who run short on time. Look for a software provider that offers comprehensive onboarding support to ensure your staff can use their new tools with confidence.
But remember: the journey doesn’t end at activation. Your PMS should set you up for success from the beginning and continue to deliver resources and support long after onboarding is complete. Lackluster client support introduces inefficiencies and frustration into your operations, so you’ll want to choose a PMS with a dedicated, knowledgeable, and accessible customer support team.
Streamline doesn’t jump ship after you sign your contract. In addition to comprehensive onboarding support, you’ll have access to a knowledge base with thousands of articles, so you can often solve issues yourself without ever picking up the phone. When a problem does call for more hands-on assistance, our North America–based support team is here to walk you through the solution.
Testing & Continuous Improvement
Before making a final decision, take advantage of free trials or demos. This hands-on experience helps you confirm whether the system aligns with your workflows and offers a sense of the support you’ll receive.
The role of testing doesn’t end there. Testing and auditing the new system before activation—running test bookings, checking for discrepancies, and simulating peak booking periods—prepares teams to identify and fix potential issues before they impact live operations.
And after go-live, continuous improvement is key. Tracking KPIs, monitoring feedback, and engaging with new updates ensures you’re always maximizing your investment.
Your software itself should continuously improve, too. The vacation rental world and technology both change rapidly, so it’s important to choose software that keeps pace with innovation. A stagnant system can quickly become outdated.
Streamline’s roadmap is guided by requests from real users, ensuring the platform reflects the tools property managers need today—not the tools they needed a decade ago. This continuous development helps your PMS remain a long-term solution, no matter how the industry changes.
Bottom Line
Switching software is a marathon, not a sprint—but it can also be a turning point. By preparing thoroughly, prioritizing support, seeking innovation, and demanding transparency, you’ll set your business up for long-term success.
Streamline was built by property managers, for property managers—and it’s trusted by some of the industry’s largest operators to deliver measurable results. When you’re ready to choose the right vacation rental software, Streamline is ready to prove why it’s the last PMS you’ll ever need.