Maintenance Supervisor

COMPANY OVERVIEW:

The Cottages on The Key is a luxury vacation rental management company in Siesta Key, Florida. We are dedicated to providing exceptional hospitality and sharing the best experiences in the area with guests from around the world.

We also offer comprehensive property management services for vacation rental owners. Our personalized "white glove" services are tailored to meet the financial goals and unique qualities of each property, resulting in our success and continued growth.

At The Cottages on The Key, we prioritize our culture. We foster a supportive and inclusive environment where everyone is valued. Our team is united and collaborative, allowing us to maintain an excellent work-life balance.

POSITION SUMMARY:

The Maintenance Supervisor is responsible for leading all aspects of property upkeep, repairs, and preventive maintenance across a portfolio of luxury properties. This role ensures that every home is maintained to the highest standards, protecting long-term asset value while providing an exceptional experience for both owners and guests. Working closely with the operations team, property owners, and trusted vendors, the Maintenance Supervisor delivers efficient, timely, and high-quality maintenance solutions.

Key responsibilities include maintaining detailed records for audits, warranty claims, and insurance purposes; serving as the primary maintenance liaison for property owners on major projects or urgent concerns; and executing essential tasks such as installing locks, security devices, and other equipment to meet company and owner standards. The role also involves collaborating in the office with the operations team to review, approve, and prioritize daily work orders, as well as completing all required maintenance for newly onboarded properties prior to listing.

RESPONSIBILITIES:

• Perform detailed maintenance inspections for every property on a quarterly basis, ensuring all systems, fixtures, safety features, and amenities are in optimal condition.
• Track property vacancies and coordinate inspections, maintaining a consistent inspection schedule.
• Identify and resolve issues found during inspections, either by completing repairs personally or coordinating with qualified vendors.
• Oversee and support the maintenance team in executing assigned tasks, ensuring quality standards and timely completion.
• Monitor progress and close out work orders in the company’s maintenance management system.
• Oversee the maintenance team, provide guidance and support with any challenges they encounter. Assist operations team with hiring and training new maintenance members
• Ensure adequate after-hours coverage and monitor the maintenance communication channels to assist as needed.
• Conduct the first comprehensive maintenance inspection to establish a baseline condition report.
• Meet with owners alongside the operations team when required, providing clear updates on property condition, ongoing maintenance work, and repair recommendations.
• Oversee large-scale projects, emergency repairs, and specialized vendor work, ensuring quality, budget compliance, and timely completion.
• Source, vet, and manage vendor relationships, negotiating pricing and monitoring performance to maintain high service standards.
• Ensure all properties meet safety codes, environmental regulations, and manufacturer specifications.

QUALIFICATIONS:

• 3+ years of experience in property maintenance supervision, facilities management, or a related role (luxury or vacation rental experience preferred).
• Strong knowledge of HVAC, plumbing, electrical, and general building systems.
• Experience managing vendors, budgets, and multiple projects simultaneously.
• Ability to work in a fast-paced, high-expectation environment with attention to detail.
• Strong communication and problem-solving skills.
• Proficiency in maintenance management software and digital work order systems.

Key Skills & Attributes

• Proactive problem-solver with a hands-on approach.
• High standards for quality, cleanliness, presentation, and communication
• Strong organizational skills with the ability to prioritize and meet deadlines.
• Ability to remain calm and effective during urgent or emergency situations.
• Commitment to delivering an exceptional owner and guest experience.

COMPENSATION & BENEFITS:

Annual Salary: $50,000 - $70,000 based on experience

Benefits

• Paid time off such as PTO, sick days, and vacation days
• Health insurance
• Paid time off such as PTO, sick days, and vacation days
• Health insurance

Schedule

• Full Time, Monday - Friday. Available via phone on weekends when necessary