US Vacation Rental Tax Lead

Keystone Bookkeepers; Manila; Remote; PHP 5,025,000 - 7,538,000; Full time

Benefits offered by this job

Paid training

Work from home

Opportunities for promotion

Job summary

Keystone Bookkeepers is seeking a US Vacation Rental Tax Lead to oversee tax compliance for vacation rentals across the United States. The role requires strong leadership, multi-state tax knowledge, and hands-on management of tax filings and client interactions.

The successful candidate will review reports from rental platforms, mentor junior staff, and help improve tax workflows while working in a fully remote environment. Competitive salary and growth opportunities are offered.

Qualifications

• Bachelor’s degree in Accounting, Fin, or related fields.
• Proven experience in US vacation rental or short-term rental tax compliance.
• Minimum of 3 years of tax experience, including 2 years in leadership.
• 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.
• Remote/virtual work experience.
• Urgency, deadline-driven, and highly organized.
• Exceptional written and verbal communication for client interaction.

Responsibilities

• Prepare, review, and file US vacation rental taxes (sales, lodging, TOT, and related taxes).
• Ensure timely tax filings across multiple states, counties, and cities.
• Review rental income reports from platforms like Airbnb and VRBO.
• Assist onboarding related to vacation rental tax compliance.
• Review work by junior tax associates and admins.
• Mentor junior team members with questions and training.
• Maintain tax workflows, SOPs, and compliance trackers.
• Communicate with US clients regarding filings, registrations, and notices.
• Respond to tax notices and inquiries from authorities.

Skills

US vacation rental tax compliance

Leadership

Multi-state tax regulations

Analytical skills

Client communication

Education

Bachelor's degree in Accounting/Finance

Tools

Spreadsheets

Cloud-based tax platforms

Job description

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.

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, Fin, 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