Seasonal Island Caretaking Team - House Island (housing provided)

Prentice Organization•Portland, OR

1d•Onsite

About The Position

Maine Harbor Club is a private island hospitality property on House Island in Casco Bay, minutes from downtown Portland, Maine. The island is home to three waterfront homes and operates as a short-term rental and private event destination from May through October. Guests arrive by boat and expect a seamless, high-standard experience from arrival through departure. We are seeking a couple or two-person team to serve as our live-in seasonal caretaking duo for the 2026 season. One person will focus on facilities, grounds, and maintenance; the other on housekeeping, interiors, and guest readiness. Cross-coverage between the two roles is expected, and both team members will be actively involved in guest interaction throughout the season. This is a property caretaking role with a strong hospitality component. During the main summer season, weekend presence and availability is required, and evening hours will be needed on a regular basis — particularly around guest arrivals, departures, and on-property events. Local candidates who prefer to commute rather than live on-island are welcome to apply.

Requirements

A two-person team with complementary skills and a shared work ethic
High standards for cleanliness, maintenance, and presentation
Self-motivated and comfortable working with minimal supervision in a remote setting
Reliable, communicative, and respectful of guest privacy
Physical ability to lift 40+ lbs and navigate boats, docks, and uneven island terrain
Comfortable with island life, water access, and seasonal operations
Background in yacht crew, private estate caretaking, or luxury hospitality strongly preferred

Nice To Haves

Access to a personal small vessel — a skiff or similar boat for personal transportation and supply runs between the island and the mainland.

Responsibilities

Grounds maintenance including weekly mowing, trimming, edging, and seasonal landscaping
Oversight of irrigation systems and water management
Routine maintenance and upkeep of all mechanical and utility systems
Dock, septic, and island infrastructure management and monitoring
Light construction, repairs, and general handyman work across all homes
Coordination with outside vendors and service providers requiring island access
Equipment upkeep including mowers, generators, and island vehicles and vessels
Spring opening and fall winterization of the full property
Monitoring and reporting of any maintenance issues requiring outside attention
Assist with housekeeping and turnover preparation during high-demand periods
Prepare and reset all homes to high hospitality standards before and after every guest stay
Manage all linens, laundry, household restocking, and overall property presentation
Ensure homes are guest-ready for short notice bookings
Maintain organized inventory of cleaning supplies, guest amenities, and household essentials
Conduct post-turnover inspections and maintain consistent quality standards across all homes
Use the Hostaway platform for turnover planning, booking management, and housekeeping scheduling
Coordinate closely with management on all upcoming arrivals, departures, and special guest requests
Seasonal cleaning projects including window washing, deep cleans, and property preparation
Assist with facilities and outdoor tasks during slower rental periods
Engage with guests professionally and warmly throughout the season
Welcome guests on arrival and assist with luggage, island orientation, and settling in
Coordinate boat arrivals and departures
Anticipate guest needs and communicate proactively with management
Maintain a visible, professional presence on the property during guest stays
Actively participate in the setup, execution, and breakdown of any events or private gatherings held on the property
Respond to guest requests and on-property needs during evenings and weekends as required