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Maine Street Property Management is a family-owned business in Wells, Maine.
We are a dedicated, hardworking, tight knit team striving to exceed our client’s expectations every day.
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Cleaning Manager – Luxury Vacation Rentals

Location: Wells, ME

Pay: Salaried $55,000 to $60,0000 per year (based on experience)

Location: Wells, Maine
Job Type: Full-Time | Salaried | Year-Round
Reports To: Director of Vacation Rentals

Compensation & Benefits

  • Health insurance (70% company paid)
  • Dental insurance
  • Vision insurance
  • Life insurance/STD/LTD (100% company paid)
  • Paid time off
  • Company vehicle provided
  • Cell phone reimbursement ($50/month)

Position Summary

Maine Street Property Management is seeking a full-time, year-round Cleaning Manager to lead cleaning operations across our portfolio of luxury vacation rentals in Southern Maine.

This is a hands-on leadership role focused on recruiting, training, and managing a high-performing cleaning team while ensuring every property consistently meets Maine Street’s white-glove standards. The position works closely with the Director of Vacation Rentals and plays a key role in guest experience, operational excellence, and property presentation.

Key Responsibilities

Cleaning Operations & Team Leadership

  • Recruit, hire, onboard, and train cleaning staff
  • Build and manage a dependable, high-performing cleaning team
  • Schedule and coordinate cleaning assignments and turnover coverage
  • Perform inspections and quality-control checks across properties
  • Provide hands-on support during peak turnover periods
  • Coach, support, and manage team performance

Property Operations & Guest Readiness

  • Ensure all homes are consistently guest-ready and maintained to luxury standards
  • Assist with guest-related property issues and urgent operational needs
  • Coordinate with maintenance staff and outside vendors as needed
  • Help maintain inventory, linens, supplies, and property organization
  • Support staging and presentation of homes for photography and marketing

Inspections & On-Call Support

  • Conduct routine property inspections
  • Identify and communicate maintenance concerns proactively
  • Participate in after-hours on-call rotation for urgent guest/property issues
  • Assist with seasonal preparation and operational improvement projects

What We’re Looking For

  • Leadership experience in housekeeping, hospitality, or property operations
  • Proven ability to recruit, train, and retain staff
  • Strong organizational and communication skills
  • Hands-on, lead-by-example management style
  • Ability to thrive in a fast-paced environment
  • High attention to detail and commitment to luxury service standards
  • Comfortable using technology and operational systems
  • Weekend availability during peak turnover periods

Schedule Expectations

This is a full-time, year-round role that requires flexibility based on seasonal business needs. Weekend availability is required during peak turnover periods, especially Fridays through Sundays in the summer season. Participation in an after-hours on-call rotation for urgent guest or property issues is also required.

About Maine Street

Maine Street Property Management manages a growing portfolio of luxury vacation rentals throughout Southern Maine, focused on thoughtful service, exceptional stays, and high-quality property care. We are seeking motivated team members who take pride in hospitality, presentation, and creating exceptional guest experiences.

Please fill out the form below or email a cover letter and resume to employment@mainestreetpm.com to apply.

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Skye Ouellette

Owner / CEO

Skye is the CEO of Maine Street Property Management. She founded the company after leaving the corporate world, where she built a successful career as a consultant and project manager. Under her leadership, Maine Street has grown into a leading property management firm, known for its expertise and commitment to excellence.

Skye and her husband, Joe, are passionate about real estate, and experienced property investors, actively expanding their extensive portfolio of residential and commercial rental properties in the Wells area. From hands-on, sweat equity renovations in their investing early days to now having a full maintenance staff and overseeing multi-million dollar renovation projects, Skye and Joe have built a reputation as industry experts in real estate investment, property rehabilitation, and large-scale renovations. Skye has made it Maine Street’s mission to help real estate investors tap into this wealth of knowledge and continue building their portfolios with confidence.
 

As a licensed Real Estate Broker with Anne Erwin Sotheby’s International Realty in York, Skye is a real estate expert.  Her focus is 100% on running Maine Street, so she rarely is active in the sales world these days, however she strongly collaborates with her colleagues at Anne Erwin to provide comprehensive real estate services—from deal analysis and negotiation to purchase—seamlessly transitioning into full-service property management.

Outside of work, Skye enjoys spending time with her family and their dog, Charlie. She has a passion for flower gardening and loves taking in the beauty of Maine’s beaches.