Virtual Assistant

Job Overview CS Outsource is seeking a detail-oriented and tech-savvy Short-Term Rental (STR) Virtual Assistant to support vacation rental operations, guest communications, and property management workflows. The ideal candidate will have 1–2 years of experience in short-term rental or vacation rental management, with hands-on experience using Streamline PMS and Breezeway strongly preferred. This role requires excellent organizational skills, strong problem-solving abilities, and the ability to manage daily operations efficiently. Key Responsibilities Guest Communication Manage guest inquiries and communications before, during, and after stays. Respond promptly and professionally to guest requests and concerns. Coordinate check-in and check-out information and provide relevant property details. Follow up on guest issues to ensure timely resolution and satisfaction. Property & Reservation Management Update property listings, reservations, and availability calendars within the PMS. Maintain accurate property information, booking details, and operational records. Monitor reservation changes and coordinate updates with relevant team members. Ensure property details and guest information remain accurate across systems. Turnover & Housekeeping Coordination Coordinate cleaning schedules and property turnovers between guest stays. Use Breezeway to track cleaning tasks, inspections, and turnover progress. Follow up with housekeeping teams to confirm property readiness. Coordinate quality assurance inspections and report any issues. Maintenance & Vendor Coordination Create and manage maintenance tickets for reported property issues. Coordinate vendor dispatch and follow up on outstanding maintenance requests. Track repair progress and communicate updates to the appropriate teams. Escalate urgent maintenance issues to help minimize guest disruption. Operations & Administrative Support Maintain accurate records of guest issues, turnover status, and operational metrics. Monitor daily tasks and ensure deadlines are met. Identify operational problems and take appropriate action. Support reporting, documentation, and other property management tasks. Requirements 1–2 years of experience in short-term rental or vacation rental property management support. Fluent written and spoken English. Hands-on experience with Streamline PMS and Breezeway is strongly preferred. Familiarity with property management systems and property operations tools. Strong understanding of guest communication, reservations, turnovers, and maintenance coordination. Excellent problem-solving, critical-thinking, and organizational skills. High attention to detail and effective time management. Ability to learn new software quickly, ideally within 3–5 days. Ability to work independently in a fast-paced operational environment. Preferred Qualifications Experience supporting US-based vacation rental or property management companies. Familiarity with housekeeping, maintenance, and quality assurance workflows. Experience coordinating multiple properties and managing competing priorities. Ability to maintain accurate operational records and provide timely updates. Tools & Platforms Property Management System: Streamline PMS Property Operations & Turnovers: Breezeway Related Tools: Other PMS, housekeeping, maintenance, and task management platforms The Ideal Candidate We're looking for someone who: Is organized, proactive, and detail-oriented. Communicates clearly and professionally with guests and vendors. Takes ownership of tasks and follows through without constant reminders. Remains calm when handling urgent guest or property issues. Learns new systems quickly and adapts to changing workflows. Prioritizes property readiness and guest satisfaction. Working Environment This is a remote role supporting short-term rental operations. Working hours and scheduling requirements will depend on the client's needs. How to Apply If you have experience in STR property management, understand vacation rental operations, and have worked with Streamline PMS or Breezeway, we'd love to hear from you! Please submit your updated CV highlighting your relevant property management experience, software expertise, and guest communication or turnover coordination responsibilities. Show more Show less