SkyRun 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.
SkyRun 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 SkyRun 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