Vacation Rental Assistant Jobs (NOW HIRING)

Penny Realty is looking for a capable, organized, and service-oriented Vacation Rental Specialist to join our growing Vacation Rental team.

This is a diverse, hands-on position for someone who enjoys variety and wants to learn all aspects of vacation rental property management. Working closely with our Vacation Rental Manager, you will assist with everything from guest reservations and property inspections to owner communication, maintenance coordination, and resolving issues that arise during guest stays.

No two days are exactly alike. Part of your time will be spent in our Pacific Beach office managing reservations, communicating with guests and property owners, updating property information, and handling administrative responsibilities. You will also spend time in the field inspecting vacation rental properties, identifying maintenance or damage issues, and helping ensure our homes are ready for incoming guests.

Because vacation rentals operate seven days a week, this position may occasionally require handling urgent guest or property issues outside normal business hours, including some weekend hours.

We are looking for someone professional, dependable, detail-oriented, tech-savvy, and an excellent communicator. Just as importantly, you should have good judgment and the ability to communicate tactfully and professionally with property owners, guests, coworkers, and vendors. This is a full-time position with competitive compensation, excellent benefits, and the opportunity to grow within an established San Diego property management company.

If you are looking for a position where you can learn multiple aspects of vacation rental management, spend time both in the office and in the field, solve problems, help people, and become an important member of a small team, we encourage you to apply.

$60,000 - $70,000 per year depending on experience

• Assist the Vacation Rental Manager with the day-to-day operation of our vacation and mid-term rental portfolio.

• Process reservations, bookings, cancellations, extensions, and other guest requests.

• Communicate professionally and promptly with vacation rental guests before, during, and after their stays.

• Communicate with property owners regarding their homes, reservations, maintenance needs, property condition, and other operational matters.

• Conduct thorough inspections of vacation rental properties to ensure they meet our standards for cleanliness, condition, safety, and guest readiness.

• Identify and document property damage, maintenance problems, missing items, and other issues requiring attention.

• Prepare clear and detailed inspection reports, including photographs and recommended corrective action when appropriate.

• Coordinate with maintenance vendors, cleaners, and other service providers to resolve property issues promptly.

• Help troubleshoot guest concerns and property emergencies and determine the appropriate course of action.

• Assist with occasional after-hours guest or property emergencies as part of the Vacation Rental team.

• Maintain accurate property information, reservation details, and other information within our vacation rental software and website.

• Assist with onboarding new vacation rental properties and ensuring property information, amenities, photographs, and operating instructions are accurate.

• Monitor upcoming arrivals and departures and help ensure properties are properly prepared for guests.

• Develop a working knowledge of each property so you can effectively assist guests, owners, vendors, and other team members.

• Stay informed about vacation rental industry practices and applicable local regulations.

• Identify opportunities to improve guest service, owner service, property inspections, and department procedures.

• Be willing to learn all aspects of the Vacation Rental department and provide backup coverage when needed.

• Strong written and verbal communication skills are essential.

• Excellent customer service skills and the ability to communicate professionally with property owners and guests.

• Strong organizational skills with the ability to manage multiple priorities in a fast-paced environment.

• Detail-oriented with the ability to recognize property condition and maintenance issues.

• Good judgment and problem-solving ability, particularly when dealing with unexpected guest or property issues.

• Comfortable learning and using vacation rental software, websites, email, texting, and other technology.

• Ability to work independently while also functioning effectively as part of a small team.

• Dependable, accountable, and willing to take ownership of responsibilities.

• Previous experience in vacation rentals, property management, hospitality, hotels, residential real estate, home inspections, maintenance, or a related field is preferred.

• Working knowledge of basic residential systems—including plumbing, HVAC, electrical, appliances, and security systems—is helpful.

• High school diploma or equivalent required; college education is a plus.

• Valid driver's license and ability to travel locally by car.

• Flexibility to assist with occasional after-hours emergencies and work some weekends.

Benefits

• Medical and Dental Insurance

• 401(k) with company match

• Paid vacation and sick leave

• Mileage reimbursement

For over 60 years, Penny Realty has been a trusted name in San Diego property management.

Our Vacation Rental team manages professionally operated vacation and mid-term rental properties throughout the San Diego area. We believe successful property management requires more than technology—it requires excellent service, sound judgment, attention to detail, and strong relationships with our property owners and guests.

Our Pacific Beach office offers ocean views, a professional team environment, and the opportunity to grow with an established company that values integrity, service, accountability, and long-term relationships.