The Best STR Operations Software for Hostaway Integration Property Managers in Boston

The Keepers + Hostaway integration is designed for one purpose: turning reservation data into executed operations. When a property manager in Hostaway Integration connects Keepers to their Hostaway account, the systems begin working together automatically.

Here is the workflow: A guest books a property in Hostaway Integration. That reservation data flows to Keepers. Keepers uses the checkout and check-in times to create a cleaning job, automatically assigned to the right cleaner based on property, location, and turnaround window. The cleaner receives a notification with property-specific details: address, key location, checkout time, guest name, and the property-specific cleaning checklist.

The cleaner arrives, completes the checklist, takes photos, and submits completion through the Keepers cleaner app. Keepers AI Quality Assurance immediately reviews the photos, looking for common issues: uncleaned surfaces, unmade beds, leftover items, missing supplies, bathroom concerns. If AI detects anything, it flags it immediately. The property manager in Hostaway Integration sees the flagged issue and can contact the cleaner for correction before the next guest checks in.

Meanwhile, Keepers tracks maintenance visibility. If a cleaner reports a broken appliance, a leaky faucet, or a maintenance issue, that report is captured immediately and linked to the property record. It does not get lost in a text thread. The property manager can assign the issue to a maintenance provider from Keepers' marketplace, or use an existing vendor—either way, the issue is tracked from assignment through completion.

Inventory status is also captured at the property level. If restocking is required, the cleaner confirms it as part of the job checklist. If supplies are missing, they are noted and flagged. Hostaway Integration property managers always know which properties are fully stocked and which need restocking before the next guest.

This entire workflow—reservation to cleaning to verification to readiness confirmation—happens without the property manager manually coordinating across multiple systems. Hostaway Integration operators report this integration saves 10-15 hours per week and dramatically improves operational consistency.

Hostaway Integration property managers manage properties across Boston's neighborhoods—Back Bay, South Boston, Beacon Hill, Downtown, Jamaica Plain, and beyond. This geographic spread makes maintenance coordination difficult. A plumbing issue in one property, a broken appliance in another, and a loose doorknob in a third—all happening simultaneously. Without a system, maintenance issues get reported via text, email, and phone calls, and the property manager has no way to see the full picture of what needs attention across the portfolio.

Keepers centralizes maintenance visibility for Hostaway Integration operators. Any issue—reported by a cleaner during turnover, by a guest during their stay, or by the property manager during an inspection—is captured in Keepers and linked to the specific property. The property manager can see every open maintenance issue across their Hostaway Integration portfolio at once, prioritize by urgency, and assign to a service provider from Keepers' marketplace or use an existing vendor.

Once assigned, the maintenance workflow is transparent. The service provider receives the job details, acknowledges acceptance, arrives at the property, completes the work, and submits confirmation (often with photo proof). The property manager sees the status at every step. When the work is complete, the issue is resolved and marked closed. This creates a permanent maintenance history for every property in Hostaway Integration—useful for insurance claims, owner reporting, and identifying recurring issues.

Inventory management works similarly. Keepers tracks supply levels at the property level. After every cleaning in Hostaway Integration, cleaners confirm restocking as part of the job checklist. If supplies are low or missing, they are flagged. The property manager can see which properties need restocking before the next guest—avoiding the scenario where a guest arrives and finds missing toilet paper, soap, or linens. For Hostaway Integration operators, restocking is automated: standing orders with local suppliers, or cleaner-confirmed restocking during turnovers.

Maintenance history and inventory status are linked to property records in Keepers, so when reviewing the operational health of a Hostaway Integration property, the manager has full visibility: cleaning status, maintenance history, inventory status, and guest readiness. This comprehensive view is impossible in fragmented systems.

Hostaway Integration property managers can connect Keepers to their Hostaway account in minutes. The process is straightforward: sign up for Keepers, authenticate your Hostaway account through the integration settings, and select which properties you want to manage through Keepers.

Once connected, Keepers begins pulling reservation data from Hostaway automatically. Upcoming reservations flow into Keepers, creating cleaning jobs based on checkout and check-in times. Property managers define their cleaning checklist once, and it applies to every turnover. They set their cleaner assignments—either from the Keepers marketplace or their own team—and Keepers handles the notifications and tracking.

For Hostaway Integration operators, the onboarding process typically takes one week from signup to first full turnover workflow. During that week, the Keepers team helps the property manager configure property-specific checklists, set cleaner assignments, define maintenance escalation rules, and connect guest communication. By the end of the week, the system is operational.

Many Hostaway Integration property managers start with one property to test the workflow, then expand to their full portfolio. The second and third properties onboard much faster because the checklist and workflow templates are already defined. By week three or four, Hostaway Integration operators typically have their full portfolio running through Keepers.

The cost is customized based on property count, which features you use, and whether you access the marketplace. For a 10-property Hostaway Integration operation, typical monthly cost is $400-600. For a 30-property operation, $1,000-1,500. This is significantly less than the cost of hiring additional operations staff or the revenue loss from operational failures like missed cleanings or guest complaints.

Hostaway Integration property managers interested in connecting Keepers to their Hostaway account should schedule a demo with the Keepers team. The demo covers integration walkthrough, feature overview, pricing based on portfolio size, and next steps. Most Hostaway Integration operators who see the system in action move forward with setup within days.