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.
We are seeking a reliable and detail-oriented Property Inspector to join our team at SkyRun Vacation Rentals - Anna Maria. In this role, you'll be the essential quality checkpoint between our cleaning teams and our guests, ensuring every property meets our high standards before each arrival. You'll work independently across our portfolio of vacation rentals in the Bradenton area, conducting thorough pre-arrival inspections, identifying issues, and coordinating swift resolutions. This position is perfect for someone who takes pride in consistency, values systems and procedures, and enjoys creating exceptional experiences through meticulous attention to detail.
Perform thorough inspections of short-term rental locations prior to guest check-in
Verify cleanliness, staging, and overall presentation
Ensure all amenities are in place (linens, toiletries, kitchen items, etc.)
Check functionality of:
HVAC systems
Appliances
TVs/WiFi
Locks and entry systems
Identify maintenance, cleanliness, or safety issues
Document findings with photos and notes
Coordinate with cleaning crews and maintenance vendors for quick resolution
Complete minor fixes when possible (light bulbs, batteries, simple repairs)
Ensure all properties meet SkyRun brand standards
Re-inspect properties when issues have been addressed
Maintain consistency across all locations
Use company software (e.g., Breezeway) to:
Complete inspection checklists
Log issues and updates
Communicate with team members
Provide clear and timely updates to operations team
Travel between properties throughout Bradenton and surrounding areas
Manage daily inspection schedule efficiently
Be available for occasional same-day or urgent inspections
Strong attention to detail and high standards for cleanliness and presentation
Ability to work independently and manage time effectively
Comfortable using mobile apps and property management software
Reliable transportation and valid driver's license
Ability to lift up to 45 lbs and handle light maintenance tasks
$45,000 - $55,000
Quarterly bonus based on quality of guest ratings.
Paid time off such as PTO, sick days, and vacation days
Health, Dental, and Vision insurance
Workplace perks such as recreation activities, food and coffee, and flexible work schedules
Employee recognition programs
Negotiable, Weekends required.