Should I do Short Term Rentals?

There’s no doubt that real estate investors can make a lot of money offering their properties as short term rentals, often referred to as “STR” or vacation rentals. Real estate investors need look no further than the meteoric rise in popularity of systems such as Airbnb and VRBO to see the potential growth of the vacation rental market. 

But trying to figure out whether short-term or long-terms rentals make the most sense for a particular property can be a confusing and complex process! Among other things, STR landlords must understand:

  • Municipal ordinances and restrictions on short-term rentals.
  • Zoning and permitting requirements for short-term rentals.
  • Demand for vacation rentals. 
  • How to calculate occupancy a nightly rate.
  • Occupancy and vacancy rates for specific areas. 
  • Best practices for bookings, deposits, cleaning, maintenance, and turnovers. 
  • Tools, insurance, benefits, and limitations of Airbnb, VRBO, and other systems

The video below presents a deep dive into short term rentals, including a discussion about how a single mistake can shut down your vacation rental:

Jeff Copeland

Jeff Copeland is the Broker/Owner of Copeland Morgan LLC. Recognized as one of the best property management companies in St. Petersburg, FL by Expertise.com in 2020 and 2021, and more recently by Home Team in 2026, Copeland Morgan LLC provides full-service real estate sales and property management in St. Petersburg and across the Tampa Bay area. Licensed as both a Florida real estate broker and a certified residential contractor, Jeff also owns Copeland Construction & Restoration LLC He is a 22-year military veteran and holds a master's degree in public administration and a bachelor's degree in management and international business. In addition to decades of experience across federal, state, and local government, Jeff has owned, operated, and sold multiple Florida businesses. He is also the founder and CEO of The Jackson Copeland Foundation, a charity in St. Petersburg, Florida dedicated to supporting leukemia patients and their families while sponsoring high-impact leukemia research.