Controller - Vacation Rentals

Mainsail Lodging & Development; Tampa (FL); On-site; USD 110,000 - 140,000; Full time

Job summary

Mainsail Lodging & Development is seeking a Controller to oversee a portfolio of vacation rental properties and condominium associations. Based in Florida, the role directs a staff accountant, manages month-end close, tax compliance, budgeting, and financial controls, while partnering with operations and association boards.

The position offers leadership responsibility, cross-functional collaboration, and opportunities to influence financial strategy for multiple properties across Anna Maria

Qualifications

• Associate degree in Accounting, Finance, Business Administration, or related field.
• 7+ years of progressively responsible accounting experience; vacation rental and condo association experience preferred.
• Demonstrated knowledge of month-end close and financial reporting processes.
• Experience handling sales/occupancy tax filings for lodging-related entities.
• Strong written and verbal communication skills.
• Experience with vacation rental software (Escapia, Guesty, Track, Breezeway).

Responsibilities

• Oversee monthly vacation rental property owner distribution statements and payments.
• Oversee Accounts Receivable activities, including billing, collections, and reconciliations.
• Oversee Accounts Payable activities.
• Manage the month-end close to ensure deadlines and accuracy.
• Review and coordinate monthly financial reporting packages."],
• CoT_job_summary_short":"COMPANY NAME: Mainsail Lodging & Development\nKEY POINTS: Vacation rental accounting, condo associations, leadership role" ,
• job_summary_short":"<p>Mainsail Lodging & Development is seeking a Controller to oversee a portfolio of vacation rental properties and condominium associations. Based in Florida, the role directs a staff accountant, manages month-end close, tax compliance, budgeting, and financial controls, while partnering with operations and association boards.</p><p>The position offers leadership responsibility, cross-functional collaboration, and opportunities to influence financial strategy for multiple properties across Anna Maria Island and Tampa. Strong background in lodging accounting and vacation rental software is valued.</p>
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Skills

Financial acumen

Leadership

Communication

Problem solving

Attention to detail

Travel readiness

Education

Assoc degree in Accounting

Tools

Escapia

Guesty

Track

Breezeway

Job description

We’re looking for enthusiastic, fun, and energetic people who take the work seriously, but not themselves. Let’s see if we’re a fit. We hope so.

Reporting to the VP of Finance, this position is responsible for overseeing the finance and accounting for a portfolio of vacation rental properties and condominium associations. The role supports several vacation rental units across multiple condominium associations in Anna Maria Island, Florida. The position can either be located in the Anna Maria Island vicinity or in Tampa, Florida.

The Controller position leads a staff accountant and ultimately is responsible for the month end close, the vacation rental owner monthly distribution statements and payments, accounts receivable, accounts payable, sales and occupancy tax compliance, budgeting and forecasting, balance sheet reconciliations, cash management, financial controls and overall financial management.

The position is a key partner to the Operations team supporting the vacation rental portfolio, the board members of the Condominium Associations, and vacation rental owners.

What You’ll Do

Accounting & Financial Reporting

• The monthly preparation of vacation rental property owner distribution statements and payments
• Oversee Accounts Receivable activities, including condominium association and intercompany billing, collections, and account reconciliation.
• Oversee Accounts Payable activities..
• Oversee the month-end financial close process, ensuring required accounting activities are completed accurately and within established deadlines.
• Review and coordinate the preparation and distribution of monthly financial reporting packages.
• Ensure balance sheet reconciliations are completed accurately, supported by appropriate documentation, and reviewed within established deadlines.
• Research and resolve accounting discrepancies, unusual transactions, and reconciliation differences.
• Maintain accurate and timely accounting records in accordance with company policies and established accounting procedures.

Tax & Regulatory Compliance

• Prepare and/or coordinate monthly sales tax and occupancy tax filings and ensure applicable taxes are properly collected or accrued, reconciled, and remitted within required deadlines.
• Monitor applicable property permits, licenses, and assigned vendor contracts to help ensure required documentation remains current.
• Support compliance with applicable local requirements, company policies, and established accounting procedures.

Cash Management & Internal Controls

• Monitor bank account balances and execute approved internal account transfers as necessary.
• Maintain a strong accounting control environment designed to safeguard company, association, and owner assets.
• Periodically review accounting and operational processes to identify financial or internal‑control risks and recommend corrective actions.
• Monitor compliance with established accounting controls and standard operating procedures in compliance with trust accounting rules.
• Identify financial and operational issues, investigate root causes, and recommend practical solutions to the VP of Finance.

Budgeting, Forecasting & Financial Support

• Oversee and coordinate the preparation of annual budgets, financial forecasts, and applicable business planning activities for the assigned portfolio.
• Monitor financial performance and identify significant trends or variances requiring management attention.
• Advise the VP of Finance regarding existing or emerging accounting, financial, and operating matters affecting the assigned portfolio.
• Support property and operational leadership with financial information and analysis as needed.

Owner & Association Support

• Respond professionally and timely to accounting and financial inquiries from owners, condominium associations, property leadership, and other stakeholders.
• Participate in condominium association and owner meetings as required, providing financial information and accounting support within the scope of the position.
• Build effective working relationships with association representatives, owners, property leadership, vendors, and internal business partners.

Leadership & Administration

• Provide day-to-day supervision, direction, training, and support to accounting staff.
• Coach, develop, and evaluate accounting staff while fostering a culture of accountability, collaboration, and continuous improvement.
• Review assigned work for accuracy, completeness, and adherence to established deadlines and procedures.
• Establish priorities and coordinate accounting workflows to ensure required financial deliverables are completed on schedule.
• Travel to association meetings, owner meetings, training sessions, and assigned properties as business needs require.
• Perform other related duties and special projects assigned.

What You Will Have

• Associate degree in Accounting, Finance, Business Administration, or related field and 7+ years of progressively responsible accounting experience; or an equivalent combination of education and directly relevant experience.
• Vacation rental accounting experience, including trust accounting is highly preferred.
• Condominium association accounting experience is preferred.
• Demonstrated knowledge of month-end financial close and financial reporting processes required.
• Working knowledge of accounts payable, accounts receivable, balance sheet reconciliations, budgeting, forecasting, and financial controls.
• Experience preparing, reviewing, or supporting sales, occupancy, or other applicable lodging-related tax filings.
• Experience reviewing financial statements and identifying accounting discrepancies and financial variances.
• Strong written and verbal communication skills.
• Previous experience with vacation rental software (Escapia, Guesty, Track, Breezeway, etc.)
• Ability to communicate patiently, tactfully, succinctly, and professionally with owners, association representatives, guests, vendors, operational leaders, and employees.
• Ability to organize multiple priorities and meet recurring financial and regulatory deadlines.

Core Competencies

Financial acumen, analytical problem solving, planning & organization, communication, leadership and coaching

Physical Demand

• Ability to sit for extended periods of time
• Ability to work long hours as needed
• Must be able to travel to association meetings, owners meetings, and property visits as needed

Mental Demands

• Make sound judgments quickly
• Effectively manage recurring deadlines, month-end requirements, tax filings, association deliverables, and competing priorities.
• Able to work independently, take direction and provide direction to others
• Maintain the highest degree of confidentiality of financial and owner information appropriately
• Ability to effectively handle challenges in the workplace, including anticipating, preventing, identifying root causes, and developing practical solutions

Mainsail is an Equal Opportunity Employer and it does not discriminate on the basis of actual or perceived race, color, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy‑related conditions), gender identity expression (including transgender status), sexual orientation, marital status, parental status, military service and veteran status, political affiliation, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances.