Vacation Rental Property Management Jobs (NOW HIRING)

Casago San Diego is a locally owned and operated vacation rental property management compnay based in Carlsbad, California. Led by local real estate professionals Dave Carter, Bert King, and Erik Trogden, the company specializes in high-end coastal homes, condos, and villas, combining regional expertise with the technological backing of Casago.

We’re looking for an experienced Vacation Rental Manager to lead the day-to-day performance of a designated portfolio of vacation rental properties in North County San Diego, CA. This is a hands-on leadership role for someone who knows how to keep people, properties, and priorities moving while maintaining exceptional standards for homeowners and guests.

Reporting to the General Manager, you’ll oversee and support a team of Property Caretakers while taking ownership of portfolio performance, property standards, homeowner relationships, and escalated guest concerns. You’ll set clear expectations, identify operational issues before they become larger problems, and make confident decisions that keep the portfolio running efficiently.

Success in this role requires more than simply maintaining properties. We’re looking for a proactive leader who can develop a strong team, build trusted relationships with homeowners, hold vendors and employees accountable, and continuously improve how the operation performs. You should be comfortable balancing multiple priorities, making independent decisions, and taking ownership of results in a fast-moving vacation rental environment.

If you have a strong background in property management or hospitality operations and enjoy leading teams, solving problems, and creating consistently excellent experiences for both homeowners and guests, this is an opportunity to make a meaningful impact within a growing local operation backed by the resources of the Casago network.

Operations & Oversight

• Provide strategic oversight and direction for the daily operations of a portfolio of vacation rental properties, ensuring alignment with company goals and performance standards.

• Lead and manage the property management team, delegating tasks and monitoring their efforts to ensure properties consistently meet or exceed company standards for cleanliness, safety, and presentation.

• Plan, schedule, and oversee periodic quality assurance inspections, using discretion to identify issues and implement corrective actions that improve operational outcomes.

• Develop, revise, and enforce operational procedures and best practices designed to enhance efficiency, maximize guest satisfaction, and maintain regulatory compliance.

Team & Vendor Management

• Lead, in collaboration with the General Manager and Operations Manager, the recruitment, training, scheduling, and supervision of Property Caretakers, housekeepers, and maintenance personnel, ensuring a high-performing team aligned with company standards.

• Establish and communicate clear performance expectations; conduct regular evaluations and provide ongoing coaching and development to promote employee growth and accountability.

• Manage vendor and contractor partnerships, exercising independent judgment in negotiating service agreements, monitoring contract compliance, and ensuring quality, cost-effectiveness, and operational alignment.

Owner & Guest Relations

• Act as the primary liaison and trusted advisor for property owners, fostering strong, long-term relationships that support client retention and portfolio growth.

• Take ownership of escalated guest and owner issues, exercising independent judgment to resolve complex concerns in a manner that upholds company standards and protects business interests.

• Direct and coach the property management team to proactively build and maintain positive homeowner relationships, ensuring consistent communication and exceptional service delivery.

• Oversee the monitoring and reporting of property performance metrics, using insights to guide operational improvements and inform owners of key developments.

• Strong supervisory and team management background.

• Excellent communication, organizational, and problem-solving skills.

• Sales or business development experience preferred.

• Technical proficiency with property management software and Microsoft Office Suite.

• Primarily working in an office environment.

• Use of computers, tablets, phones and other office equipment.

• Occasional visits to properties and travel between properties – so there may be occasional outdoor work with exposure to variable temperatures and weather conditions (heat, cold, rain). Visiting properties may also involve noise, dust, cleaning agents, and potential strong odors (cleaning agents).

• Availability to work weekends, early mornings, and evenings as needed.

• Occasional assistance with inspections but primarily in an oversight and management role.

• Bachelor’s degree in Business, Hospitality, or related field preferred.

• 3+ years experience in property management, hospitality, or related leadership experience.

$70,400

• Up to 10k per year in performance bonus

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

• Health, Dental, and Vision insurance

• Retirement benefits or accounts

• Full-time, Thursday through Monday