Guest Services Virtual Assistant

Company Overview

Founded in 2011, Extraordinary Stays is a full-service property management company dedicated to making Southern California getaways seamless and unforgettable for our guests. Our team's meticulous attention to detail and hands-on experience ensure a stress-free experience from booking to checkout — and that same care extends to how we support our employees. We're looking for dedicated, detail-oriented people to join our growing team and help us deliver exceptional vacation experiences across San Diego.

Position Summary

We're looking for a Guest Services Virtual Assistant who thrives on helping others and working collaboratively with our team to deliver exceptional experiences. In this role, you'll be the welcoming voice and reliable problem-solver for our vacation rental guests throughout their stay journey. You'll work closely with our Guest Experience Agents, Operations, Housekeeping, and Maintenance teams to ensure every guest feels supported and every concern is addressed promptly. This position is perfect for someone who enjoys building connections, coordinating across teams, and taking pride in creating memorable guest experiences from booking through checkout.

Key Responsibilities

Guest Experience Liason (Primary Responsibility)

• Serve as a frontline point of contact for guests before, during, and after their stay via approved communication channels (email, messaging platforms, phone as needed)

• Support Guest Experience Agents by handling guest questions, service requests, follow-ups, and routine issue resolution

• Escalate guest issues appropriately following established guidelines

• Coordinate with Operations, Housekeeping, and Maintenance teams to help resolve guest concerns

• Monitor active stays and support in-stay guest needs

• Accurately document guest interactions, issues, and resolutions

• Assist with confirming check-in readiness and access details

• Send and follow up on check-out communications

• Support housekeeping coordination to ensure homes are guest-ready

• Flag readiness, access, or cleaning concerns promptly

Sales & OTA Administrative Support (Secondary Responsibility)

• Assist with responding to booking inquiries and routing messages appropriately

• Help maintain accurate OTA calendars to prevent booking conflicts

• Support basic OTA listing updates, audits, and special offers as assigned

• Answer and route inbound calls or messages, escalating urgent matters when required

• Participate in team meetings, training sessions, and coverage handoffs

Required Qualifications

• 1+ years experience in customer service, hospitality, or guest support roles

• Strong written and spoken English communication skills

• Reliable internet connection and ability to work remotely

• Strong attention to detail and follow-through

• Comfort working with documentation standards and escalation guidelines

• Ability to manage multiple tasks in a fast-paced environment

Preferred Qualifications

• Experience with vacation rental office management/operations

• Experience with short term rental management software (ideally Hostaway/Guesty, Breezeway, Conduit (or an AI alternative), Beyond Pricing, and/or SuiteOp

• Experience with OTAS (airbnb, VRBO, Booking.com, etc.)

Compensation, Benefits & Schedule

Hourly Rate

$8 - $12

Bonus

• 5-10% Bonus annually (Annual reviews and Bonus are paid out annually in September each year)

Benefits

• Paid time off such as PTO, sick days, and vacation days

Schedule

• T/Th/Fr/Sa/Su 8am-5pm (with 60 min lunch break) Monday Wednesday off