Same side of the county, very different feel
St. Petersburg and Gulfport are often grouped together because they share the same broad south-Pinellas orbit, but the housing, local identity, and buyer expectations are different. St. Petersburg is a full urban market with multiple submarkets inside it. Gulfport is much smaller and tends to be chosen for charm, local character, and a more niche neighborhood feel.
Where St. Petersburg tends to win
St. Petersburg wins when the buyer wants a larger menu of neighborhoods, stronger job and lifestyle range, and more flexibility in how urban or residential the final choice feels. The city can solve a lot of different problems, but that also means buyers need to compare neighborhoods carefully instead of assuming one city label explains everything.
Where Gulfport tends to win
Gulfport wins when quirky waterfront-adjacent identity, a smaller-town feel, and stronger lifestyle personality matter more than broad inventory choice. It can feel more memorable, but the housing stock, insurance considerations, and use-case flexibility can tighten quickly depending on the property type.
How to decide well
Compare the strength of the local identity you want, the insurance and property-type risk you are comfortable with, and whether you need a broad city with many paths or a smaller place that is attractive for more specific reasons.