Director of Vacation Rentals – Leadership Team
Location: Wells, Maine
Job Type: Full-Time/Salaried
Salary: $70,000+ and Bonus Eligible (commensurate with experience)
Position Summary
The Director of Vacation Rentals leads the Vacation Rental Department and serves as a senior member of the Maine Street Property Management leadership team. This role is responsible for the overall performance of the vacation rental portfolio, including bookings, pricing strategy, marketing oversight, owner relationships, and guest experience.
The Director of Vacation Rentals ensures properties are performing at their highest potential while delivering exceptional service aligned with the Maine Street brand.
Core Responsibilities
• Lead the Vacation Rental Department and contribute at a senior leadership level
• Work closely with the team to ensure strong coordination across operations, maintenance, and guest services
• Serve as the primary point of contact for all vacation rental owners, maintaining strong communication and accountability
• Take ownership of all bookings, managing inquiries, reservations, and calendars in booking software
• Develop and execute pricing strategies based on market conditions, performance data, and owner goals
• Oversee guest communications before, during, and after stays and ensure timely issue resolution
• Oversee marketing and listing content, including photography, descriptions, platform accuracy, and conversion optimization
• Regularly review property listings to ensure quality and brand alignment
• Review financial reports to monitor performance and identify revenue opportunities
• Solicit and respond to guest reviews to strengthen brand reputation and drive continuous improvement
• Support social media visibility and engagement consistent with the Maine Street brand
• Remain available to address urgent guest and owner needs as part of the on-call nature of the role
The Ideal Candidate
• 3-5 years of experience in hospitality, vacation rentals, or a related service-driven industry
• 3-5 years of experience in account management and owner/client relationship management
• 3–5 years of experience overseeing marketing initiatives, listing performance, or revenue strategy
• 2+ years of experience managing teams, vendors, and cross-department workflows
• Strong project management skills with the ability to manage multiple priorities simultaneously
• High level of accountability, ownership, and follow-through
• Tech-savvy and comfortable working across multiple systems and platforms
• Thrives in a dynamic environment with seasonal demand and high guest expectations
• Availability to work weekends during summer months as needed to oversee accounts
• Availability to remain on-call for guest and business needs, including bookings and urgent issues
• Professional, organized, and guest-focused at all times
Compensation & Benefits
• Flexible Work Environment – While we maintain a culture of responsiveness beyond traditional office hours, we also offer flexibility and trust our team to manage their time effectively
• Unlimited PTO Policy – Take the time you need to rest, recharge, and manage life outside of work
• Health, Dental, and Vision Insurance – 70% company paid
• $50/month Cell Phone Reimbursement
• 100% Company-Paid Short-Term Disability, Long-Term Disability, and Life Insurance
• Annual Performance-Based Bonuses
• Use of Company Vehicle During Work Hours for site visits, inspections, and errands
• Beautiful Office Space in Wells, Maine with state-of-the-art technology
• Energetic, motivated team environment that values collaboration, accountability, and innovation
Why Join Us?
Maine Street Property Management fosters a collaborative, forward-thinking environment where leadership, accountability, and growth are top priorities. This role offers the opportunity to make a meaningful impact and help shape the future of a growing company.
Apply today to join us in Wells, Maine.
