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