Bookkeeper — Short-Term Rental / Property Management

About the Role

We're looking for a bookkeeper with short-term rental or property management experience to join the team. You'll handle the day-to-day bookkeeping work that keeps property-level financials clean and accurate, and you'll get close to the accounting workflows we're continuously improving on the product side.

This is a strong fit for someone earlier in their career who knows their way around STR books, wants to sharpen their skills inside a growing fintech company, and is curious about how modern accounting tools are built.

What You’ll Do

• Categorize transactions, reconcile accounts, and keep the books current on a rolling basis
• Process accounts payable and receivable
• Assist with month-end close tasks, including reviewing ledgers and flagging anomalies
• Maintain owner ledgers and property-level records
• Help prepare owner statements and supporting reports
• Handle data entry, documentation, and file organization with care
• Flag recurring issues or friction points so we can address them at the workflow level
• Partner with senior accounting team members on cleanup and onboarding projects

Qualifications:

• 1-3 years of bookkeeping experience, with exposure to short-term rental, vacation rental, or property management bookkeeping
• Comfortable in QuickBooks Online
• Some exposure to a PMS (Guesty, Track, Hostaway, Streamline, OwnerRez, Rentvine, Hostfully, or similar) preferred
• Solid Excel skills
• Detail-oriented, organized, and responsive
• Willing to ask questions and learn on the fly
• Fluent English (B2+)
• Availability during U.S. business hours
• Works as an independent contractor

Benefits:

• Competitive pay based on experience
• Remote
• Paid time off
• Meaningful growth path alongside senior accountants and a technical team building the next generation of property management financial tools

How to Apply:

In your application, include 2–3 sentences describing any STR or vacation rental bookkeeping you've done and which PMS platforms you've worked with. Applications without directly relevant experience will not be prioritized.

*Topkey is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC.

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