Maintenance Technician

Company Overview

Sky Run Vacation Rentals – Anna Maria Island is a high-growth short-term rental management company dedicated to delivering exceptional guest experiences and maximizing homeowner value.

We manage a portfolio of high-end vacation homes across Anna Maria Island and operate with a hospitality-first mindset. Our team combines operational excellence, clear communication, and strong local expertise to create memorable stays for guests while protecting and enhancing our homeowners’ investments.

We believe in:

• High standards and accountability
• Clear processes and strong team communication
• Ownership mentality at every level
• Continuous improvement
• Taking pride in delivering 5-star experiences

If you thrive in an environment where details matter, standards are high, and your work directly impacts guest satisfaction and company reputation, you will fit in well here.

Sky Run Anna Maria is a growing vacation rental management company focused on delivering exceptional guest experiences and maintaining high-quality homes across Anna Maria Island and surrounding areas. We are looking for a reliable, hands-on Maintenance Technician to join our team and help keep our properties in top condition.

This position is ideal for someone who is proactive, detail-oriented, and comfortable handling a wide variety of maintenance and property-related tasks in a fast-paced hospitality environment.

• Perform routine maintenance and minor repairs at vacation rental properties
• Troubleshoot issues related to plumbing, electrical, HVAC, appliances, WiFi, TVs, locks, and general home systems
• Conduct property inspections before and after guest stays
• Respond promptly to maintenance requests and urgent issues
• Coordinate with outside vendors and contractors when necessary
• Assist with preventative maintenance programs
• Ensure properties meet Sky Run quality standards and guest expectations
• Document completed work and communicate updates with management
• Help identify potential property issues before they become major problems

• Previous maintenance, handyman, property management, or hospitality experience preferred
• Basic knowledge of plumbing, electrical, HVAC, and general home repair
• Strong troubleshooting and problem-solving skills
• Ability to work independently and manage time efficiently
• Positive attitude and team-oriented mindset
• Comfortable using smartphones/apps for communication and task management
• Valid driver's license and reliable transportation required
• Ability to lift 50+ pounds and work both indoors and outdoors in Florida conditions

• Experience in vacation rentals, hotels, or residential property maintenance
• Pool or spa knowledge is a plus
• Basic knowledge of smart home technology and WiFi systems
• Flexible availability, including occasional weekends or after-hours emergencies

$45,000 - $60,000

• Paid time off such as PTO, sick days, and vacation days
• Health, Dental, and Vision insurance
• Employee recognition programs
• Workplace perks such as recreation activities, food and coffee, and flexible work schedules