US Vacation Rental Tax Lead

US Vacation Rental Tax Lead – Job Description

About Keystone Bookkeepers

Our mission is to allow entrepreneurs to focus on running their business while we empower them with financial management and meaningful insight to drive their bottom line.

We are a rapidly growing cloud bookkeeping firm that leverages technology and automation to deliver timely, accurate, and compliant financial and tax solutions to our customers across the US.

About the Role

We are seeking a highly skilled and experienced US Vacation Rental Tax Lead for Keystone Bookkeepers. This role is responsible for managing and overseeing US vacation rental and short-term rental tax compliance across multiple jurisdictions.

As a Vacation Rental Tax Lead, you will play a critical role in ensuring accurate filing and remittance of lodging-related taxes while leading and supporting a team handling vacation rental tax operations. If you are detail-oriented, tech-savvy, and have strong experience in US short-term rental tax compliance and leadership, this role is for you.

What Your Day to Day Will Look Like

• Prepare, review, and file US vacation rental–related taxes including:
  • Sales tax
  • Lodging tax
  • Transient Occupancy Tax (TOT)
  • Other state and local short-term rental taxes
• Ensure timely and accurate tax filings across multiple states, counties, and cities
• Review rental income reports from platforms such as Airbnb, VRBO, and property management systems
• Assist with new client onboarding related to vacation rental tax compliance
• Review work completed by junior tax associates and admins
• Assist junior team members with questions, training, and ongoing support
• Help maintain and improve tax workflows, SOPs, and compliance trackers
• Communicate directly with US clients regarding tax filings, registrations, and notices
• Respond to and resolve tax notices and inquiries from tax authorities
• Other ad-hoc duties as required
  
  

What You Need to Succeed

• Preferred: Bachelor’s degree in Accounting, Finance, or related fields
• Proven experience in US vacation rental or short-term rental tax compliance
• A minimum of 3 years of relevant tax experience, including 2 years in a leadership or team lead capacity
• Strong knowledge of multi-state and local tax regulations
• Proficiency in spreadsheets and cloud-based accounting or tax platforms
• Strong analytical skills and meticulous attention to detail
• Friendly demeanor – internally and externally
• Professional experience working in a remote/virtual environment
• Strong sense of urgency, deadline-driven, and highly organized
• Exceptional written and verbal communication skills for effective client interaction
  

Work and Holiday Schedule

• Be available to work 8:00 AM – 5:00 PM EST
• Observe PH Holidays
  
  

Job Type: Full-time | Fully remote

Benefits

• Additional leave
• Opportunities for promotion
• Paid training
• Work from home
  
  

Why Join Us?

• Flexible, remote work environment
• Competitive salary
• Paid time off
• Opportunity for professional growth through exposure to complex US tax compliance
• A supportive and inclusive work environment