Bookkeeper (Vacation Rental Industry)

Howard Financial is a full-service back-office solution for high-growth companies with bookkeeping, payroll, and bespoke reporting needs that require accuracy, timeliness, and institutional-quality reporting without the burden of full-time staff. We are an experienced team of bookkeepers and administrators with multiple decades of combined experience across industries allowing companies to focus on their core business while we handle the rest.

Founded in 2023, our team of ~100 professionals supports ~75 clients across a diverse range of industries. We recently reached $6M of contracted ARR and are growing rapidly (over 200% LTM growth).

About the Role We are looking for an experienced Bookkeeper with a strong background in the Vacation Rental industry. The ideal candidate has hands-on experience with hotel accounting, managing daily transactions, reconciliations, and reporting, and is comfortable supporting leadership in financial operations.

Only English resumes will be considered.

Qualifications

• 2+ years of bookkeeping or accounting experience in short-term rentals
• Strong knowledge of hotel accounting and daily financial operations
• Skilled in SAGE, QuickBooks, Excel, and other accounting tools; familiarity with Bill.com or Ramp is a plus
• Detail-oriented, organized, and proactive
• ️ Fluent English — able to communicate effectively with clients and management
• Able to thrive in a fast-paced environment
• Availability: 9 AM–5 PM EST
• Works as an independent contractor

Benefits

• Competitive pay – based on experience
• Quarterly performance bonus – tied to team and individual results
• Unlimited paid time off
• Remote work – collaborate with a global team from anywhere
• ️ 10 paid holidays per year – choose local or U.S. holidays
• Structured schedule – standard business hours with 9–5 EST overlap
• Annual performance reviews – clear feedback and growth discussions
• Career growth opportunities – we support your development and next steps
• Learning culture – curiosity, feedback, and continuous improvement encouraged
• Supportive team – sharp, friendly people who care about great work