Breezeway

Breezeway (operating at breezeway.io) is a property operations and services platform engineered for the hospitality industry, specifically designed to streamline the management of short-term and mid-term rental properties. Founded in 2017 by the founder of FlipKey and headquartered in Boston, Massachusetts, Breezeway addresses the fragmented communication and coordination challenges faced by property managers and field teams. Under the hood, the platform leverages AI-powered tools to automate workflows, facilitate real-time messaging, and verify task completion—eliminating inefficiencies in scheduling, communication, and service verification. This allows property managers and on-site teams to coordinate work seamlessly, reduce operational bottlenecks, and deliver consistent service experiences. Backed by $36.2 million in funding across seven rounds, Breezeway has positioned itself as a critical solution for modern rental property operations, blending technology with hands-on fieldwork to enhance productivity and guest satisfaction.