Guest Services and Operations Virtual Assistant

Position Summary We are looking for a highly organized and service-driven Guest Services and Operations Virtual Assistant to support a premium short-term vacation rental business. This role is responsible for managing guest communication, coordinating check-ins and check-outs, overseeing same-day turnovers, handling operational issues, and ensuring guests receive prompt, warm, and professional support throughout their stay. The ideal candidate is calm under pressure, detail-oriented, solution-focused, and comfortable taking full ownership of day-to-day operations with minimal supervision. This role directly impacts guest satisfaction, operational efficiency, and overall service quality. In addition to guest-facing responsibilities, this role requires strong follow-through with housekeeping and maintenance teams, sound judgment in managing same-day turnovers, and the ability to proactively ensure smooth operations and positive guest experiences. Job Details Work Arrangement: Work from Home Schedule: Split shift aligned to Hawaii peak guest support hours Hawaii Time: Monday to Friday | 7:00 AM to 11:00 AM and 4:00 PM to 8:00 PM Manila Time: Tuesday to Saturday | 1:00 AM to 5:00 AM and 10:00 AM to 2:00 PM Holiday Schedule: Will follow major US Holidays Responsibilities Guest Communication & Experience Manage guest communication across active reservations and respond promptly to inquiries, requests, and concerns Provide clear, warm, and reassuring communication, especially during delays or service disruptions Support guest check-ins and check-outs, including handling early/late requests within guidelines Assist guests with access issues, navigation, gate entry, parking, and property-related concerns Ensure all guests receive complete and accurate pre-arrival information (instructions, codes, directions, parking, etc.) Monitor pre-arrival completion steps and proactively follow up with guests who have not completed required check-in requirements Operations & Turnover Management Oversee same-day turnovers and exercise strong judgment in identifying and addressing potential delays Communicate realistic check-in timelines to guests when necessary to manage expectations Coordinate closely with housekeeping to ensure turnovers are completed on time and to standard Follow through on all housekeeping and maintenance tasks—not just assigning, but confirming acknowledgment, tracking progress, and ensuring completion Housekeeping & Maintenance Coordination Communicate special cleaning requirements, damage reports, missing items, and maintenance issues Ensure all issues are acknowledged, timelines are confirmed, and updates are tracked through resolution Log and document all maintenance concerns, guest complaints, and operational issues requiring follow-up Provide timely updates and reassurance to guests during cleaning or repair delays Daily Operations Oversight Review overnight messages, new bookings, reservation changes, and guest inquiries Maintain strong awareness of property status, including arrivals, departures, and ongoing issues Develop familiarity with property-specific details, including access procedures, parking, and unique property requirements Systems & Tools Utilize property management systems (e.g., Hostaway) to manage reservations, guest communication, and operational workflows Adapt quickly to internal tools and communication platforms (e.g., Slack or similar systems) to ensure seamless coordination with the team Support phone-based guest communication where calls may be routed during active shifts Judgment & Escalation Operate independently and apply sound judgment in resolving issues Escalate only critical issues such as safety concerns, access failures without workaround, major system failures, or guest escalation risks Qualifications Strong written and verbal English communication skills Experience in customer service, hospitality, property management, virtual assistance, or operations coordination Ability to communicate warmly, professionally, and calmly under pressure Strong attention to detail with excellent task tracking and follow-through Proven ability to manage multiple priorities in fast-paced environments Strong problem-solving skills with a solution-oriented mindset Ability to work independently and make decisions within defined guidelines Willingness to work a split shift schedule aligned to Hawaii time Comfortable handling real-time guest support and operational coordination Tech-savvy and able to quickly learn new systems and tools Nice to Have Experience in short-term rentals, vacation rentals, Airbnb, or hospitality operations Familiarity with property management systems such as Hostaway Experience coordinating with housekeeping, maintenance, or service vendors Background in handling guest complaints, service recovery, and issue logging Experience using communication tools such as Slack or similar platforms Exposure to phone-based guest support systems