Part-Time Vacation Rental Accounting & Operations Systems Specialist (Remote, U.S. Only)

***Please do not submit an automatic or generic application if you are not willing to take the time to answer the screening questions thoughtfully. I am looking for someone who is genuinely interested in this specific opportunity and has taken the time to understand the role.

Applications will only be considered if all screening questions are completed with clear, specific, and thoughtful responses. Generic, copied, or incomplete answers will not be reviewed. Please use your answers to show how your experience relates to both the financial operations and property management systems aspects of the position.***

I’m looking for a detail-oriented and highly organized professional to support the behind-the-scenes financial and systems operations of my growing vacation rental property management business.

I manage a small portfolio of privately owned vacation properties located within a resort. This is a hands-on small-business role, and you will work directly with me rather than as part of a large corporate team.

This is not a guest-facing position. Your primary responsibilities will be reconciling financial activity across multiple systems, reviewing invoices and resort statements, identifying incorrect or duplicate charges, supporting monthly owner reporting, and helping me improve how I use Guesty and related property management tools.

The role will begin at approximately 6-8 hours per week, with the potential for additional hours and responsibilities as the business grows.

Responsibilities

• Reconcile reservation payouts, processing fees, refunds, adjustments, and other financial activity across Airbnb, Guesty, and resort-issued statements
• Compare invoices, reservation records, and account statements to ensure all charges are accurate
• Identify duplicate, incorrect, missing, or unexpected charges
• Research discrepancies and clearly document findings and recommended next steps
• Review resort invoices to help ensure that the business and property owners are not being overcharged
• Organize and maintain property-level financial records and reconciliation trackers
• Assist with the preparation of monthly accounting statements and financial summaries for property owners
• Confirm that reservation, fee, payment, and property information is recorded consistently across systems
• Review the current Guesty setup and recommend improvements to reporting, workflows, automations, integrations, and overall account organization
• Help develop repeatable processes and documentation that make monthly operations more accurate and efficient
• Take ownership of recurring operational tasks and follow them through to completion, * This is a small, growing business where some processes are still being built. What appeals to you about that opportunity?
• What would you want to understand during your first two weeks in this role before recommending changes?

• Experience with bookkeeping, account reconciliation, invoice processing, accounts payable, financial operations, or a similar function
• Experience using Guesty or another vacation rental or property management platform, such as Hostaway, OwnerRez, Lodgify, Escapia, or a comparable system
• Strong Microsoft Excel or Google Sheets skills
• Ability to compare information across multiple reports and identify discrepancies
• Exceptional attention to detail and a high standard for accuracy
• Strong organizational, analytical, and problem-solving skills
• Ability to work independently and investigate issues without step-by-step direction
• Clear written communication skills, particularly when documenting financial discrepancies or process recommendations
• Comfort working directly with a small-business owner in an environment where processes are still being developed and improved
• Ability to handle financial and business information with discretion

Preferred Experience

• Experience reviewing Airbnb payouts, reservation reports, fees, refunds, and adjustments
• Experience supporting vacation rental, hospitality, resort, hotel, or property management operations
• Experience preparing property-level or owner-level accounting statements
• Experience auditing vendor invoices or identifying billing errors and overcharges
• Experience improving workflows, reports, or automations within a property management system

What I’m Looking For

The right person will combine strong financial attention to detail with a broader understanding of vacation rental operations and property management systems. You should be comfortable reconciling financial activity and investigating discrepancies, but also evaluating how information flows through Guesty and related platforms.

I’m looking for someone who can identify opportunities to improve reporting, workflows, automations, integrations, data organization, and recurring operational processes. You should be able to learn how the business currently operates, spot inefficiencies or inconsistencies, and recommend practical improvements.

Because this is a small business, you should be dependable, proactive, comfortable working independently, and willing to take ownership of both recurring tasks and longer-term systems improvements.

United States Remote $25 - $35 an hour - Part-time, Pulled from the full job description

• Flexible schedule, * Flexible schedule