TL;DR 

For growing SMBs (4+ units), the choice between Guesty and Hostaway comes down to long-term infrastructure. While Hostaway serves the small and mid-market with a standard set of core tools, Guesty Pro™ provides a deeper, “full-spectrum” ecosystem designed for lasting scale. With native trust accounting, advanced revenue management, lead management, and native transaction processing, Guesty empowers businesses to expand from a handful of units to enterprise volume without the operational friction of migrating software.

The operational crossroads: Simplicity vs. capability

For many small to medium property managers, there comes a distinct phase of growth in which simplicity loses its value and becomes a limitation. Hostaway is often recognized as a strong solution for the SMB, offering a user-friendly interface that works well for straightforward operations. 

However, as your portfolio expands beyond 10 or 20 units, operational needs become more complex. Efficient management increasingly requires rigorous financial reporting for owners, integrated risk management, trust accounting, and payment processing that was built especially for hospitality cash flows. The strategic difference lies in how each platform handles this complexity. While Hostaway typically relies on third-party integrations to fill these gaps, Guesty Pro™ provides these capabilities natively within the platform.

Choosing the right partner means evaluating not just what your business needs are today, but the infrastructure you’ll need to scale efficiently tomorrow.

Infrastructure comparison: The strategic differences

1. Financial management: Native integrity vs. integrations

As you take on more owners, the complexity of managing trust accounts and commission splits increases.

The Hostaway approach: Hostaway primarily manages financials through integrations with external accounting software (like QuickBooks) or manual exports. The platform does not offer a native trust accounting module with built-in regulatory compliance.

The Guesty advantage: Guesty Pro™ includes a native trust accounting module designed specifically for property management, with localized compliance to the most stringent local regulations, such as those in North Carolina and Queensland (AU). The platform provides cash-basis accounting, automated bank reconciliation, 1099 generation, and built-in ACH capabilities – all within a unified system to ensure utmost accuracy and compliance.   

2. Connectivity: API power and distribution

In a competitive distribution landscape, the speed and breadth of your connectivity can directly impact your revenue.

The Hostaway approach: Hostaway connects directly to approximately 26 channels. Its open API supports around 1.5 to 2 calls per second, which is sufficient for standard operations but may experience latency during high-volume periods. However, their listing sync can take up to 30 minutes, creating the risk of double bookings.  

The Guesty advantage: Guesty connects to 60+ channels and niche platforms, and has priority partnerships with all leading platforms, giving users preferred ranking to boost performance. Furthermore, Guesty’s API infrastructure supports 15+ calls per second, ensuring real-time synchronization and reducing the risk of double bookings during peak demand.

3. Business growth: Secure payment infrastructure  

As you expand, the risks multiply: chargebacks, fraud attempts, revenue leakage, split payment complexity. A built-in, secure, hospitality-first payment processor that understands your cash flow cycles stops being a preference. It becomes vital protection for your business.

The Hostaway approach: Hostaway does not currently offer a hospitality-first payment solution for its users.

The Guesty advantage: Guesty Pay™ is embedded into Guesty with a comprehensive, highly secure transaction suite providing AI-powered fraud detection, chargeback management, unified expense management, and a premium credit service built especially for hospitality.  

4. Risk management: Embedded vs. add-on

The Hostaway approach: Managing screening, travel insurance, and liability coverage involves juggling third-party tools, disrupting both your workflows and the check-in experience.

The Guesty advantage: Guesty Shield™ integrates guest screening, damage protection (up to $20k), travel insurance, and liability coverage directly into the platform, providing simplified claim management, faster payouts, and smooth resolution with zero friction. 

At a glance: Capability comparison 

Expert verdict: Investing in long-term stability

For property managers with ambitions to scale, the cost of switching platforms later is high — data migration, retraining staff, broken integrations, and weeks of lost momentum.

Guesty Pro™ is supported by the largest R&D team in the industry, ensuring the platform evolves alongside your business. By investing in a full-spectrum solution that handles accounting and high-frequency distribution natively, you build your business on a solid foundation designed for growth, not workarounds.

Guesty’s talented marketing team is comprised of passionate professionals who share insightful industry knowledge and shape brand narratives. By bringing a diverse blend of expertise to the table, we are the visionary architects behind the Guesty brand and innovative campaigns that help people understand our product.