Should You Sell or Keep Your Vacation Rental? A Smart Owner’s Guide for 2025

 

Should You Sell or Keep Your Vacation Rental? A Smart Owner’s Guide for 2025

Owning a vacation rental in Pinellas County—whether in St. Pete Beach, Madeira Beach, Clearwater Beach or Treasure Island—has long been a profitable investment and a personal escape. But in today’s changing market, more owners are asking a critical question: Should I sell or should I hold?

With rising property taxes, insurance costs, evolving short-term rental regulations, and shifting buyer demand, now may be the time to reevaluate your property's role in your financial future. Whether you're earning steady income or juggling vacancies and maintenance, this guide will help you assess whether it’s smarter to cash out or stay the course.

Across coastal Pinellas County, buyer interest remains strong for well-maintained, income-producing vacation properties, especially those close to the beach or offering water views. However, the market has become more price-sensitive in 2025, and some units are sitting longer unless priced strategically or updated with modern finishes. At the same time, vacation rental demand has stayed relatively consistent, supported by year-round tourism. Properties in high-traffic areas like Johns Pass or Upham Beach still see strong occupancy, but owners must stay competitive with pricing and amenities.

For some owners, now may be the right time to exit the market. If you've built substantial equity or your property's value has surged, selling could unlock capital for other opportunities. Other motivating factors might include increasing insurance and maintenance costs, local rule changes limiting short-term rentals, burnout from self-management or unreliable tenants, or a shifting financial picture such as retirement, downsizing, or reallocating investments.

If your rental continues to perform well and you have solid property management, holding can still make great sense. Real Estate in coastal Pinellas continues to appreciate over time, and owning a desirable location offers ongoing cash flow, tax advantages, personal vacation use, potential to 1031 exchange into another income property, and long-term appreciation in a growing region.

Many owners are feeling the pinch from higher premiums, particularly for older homes or those without wind mitigation features. Some local municipalities have also introduced stricter permitting or occupancy rules for short-term rentals, reducing flexibility for investors. Before making a decision, review your property’s net income after insurance, taxes, management fees, and repairs. In some cases, selling while the market remains favorable might make more financial sense than holding onto a property with shrinking returns.

Ask yourself if you are getting the return you expected, if you still enjoy using or managing the property, if there are new risks that weren’t there a few years ago, and if the equity could be better used elsewhere.

The right answer depends on your goals, finances, and appetite for risk. Start by running a side-by-side analysis of current net income versus projected sale proceeds. From there, consult with a local real estate expert who can provide accurate market data and help you explore your best options.

Let’s Talk Real Estate

Curious how this market—or a specific project—might impact your property value or real estate plans? Whether you're thinking about selling, buying, or just keeping an eye on trends, I’m always here to help.

Keyvan Kohan
Broker Associate, RE/MAX Metro
📞 727-204-5001
✉️ kkshohet@gmail.com
🌐 www.SunCoastHome.com