SkyRun Vacation Rentals

Meet Our Team

SkyRun Anna Maria's Local Destination Experts

Our team is composed of unique individuals with a variety of backgrounds! Our local team has a strong synergy that adapts to the dynamic business environment of vacation rental management. 

Matt & Alexa Cooper

Owners of SkyRun Anna Maria

Matt & Alexa Cooper started SkyRun Anna Maria in mid-2021 and Matt has a background in sales, education, and private equity/investment banking. After renting out properties alongside his career, he was ready for something different and made the transition to owning and operating his own vacation rental business full-time. Matt, his wife Alexa, and their daughter are based right in Bradenton, and they're your exceptional local hosts dedicated to making your Gulf Coast vacation unforgettable. Fun fact: Matt played professional basketball for several years around Europe after graduating college!

We're Hiring!

SkyRun Vacation Rentals is a rapidly growing, multi-destination property and rental management company. We're currently seeking high-quality candidates for these positions. If you're an energetic, initiative taking individual who is interested in a career in hospitality please send your resume to annamaria@skyrun.com.


Cleaning & Quality Specialist
At SkyRun, our top priority is the quality of our product. The Housekeeping Specialist is responsible for maintaining our clients' homes in pristine cleaning condition and ready for guest stays.


Visitor Satisfaction Specialist
The Inspector serves one of the most important roels at SkyRun. The Inspector carefully and diligently prepares our rental homes in order to ensure guest and owner satisfaction.


Home Protection Specialist
To ensure the upkeep of our clients' rental homes, the Maintenance Technician carries out routine maintenance, exterior care and property repair.

SkyRun Anna Maria

SkyRun Anna Maria
PO Box 21142
Bradenton, FL 34204

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