Gulfport's housing stock is defined by its historic character. Much of the city consists of older wood-frame and masonry cottages and bungalows, many dating to the town's early-20th-century origins, set on small lots along tree-lined streets. The city has adopted design guidelines for its arts district, between 49th and 59th streets south of Gulfport Boulevard, to keep new construction in character with the surrounding buildings. Waterfront homes along Boca Ciega Bay are among the most sought-after properties, offering docks and open-water views, while inland streets hold a mix of original cottages and modest single-family homes. The overall stock skews toward established, smaller-scale homes rather than large new subdivisions.

Gulfport's neighborhoods radiate from its waterfront core. The Veteran City neighborhood, in the heart of the arts district, is among the most popular, with historic cottages and bungalows a short walk from the shops and galleries of the downtown. The Historic Waterfront District, anchored by the Gulfport Casino and municipal marina, fronts Boca Ciega Bay and holds many of the town's oldest and most characterful properties. Farther inland, residential streets south of Gulfport Boulevard blend long-established homes with modest infill, while the shoreline areas offer direct access to the bay and the city's beachfront parks.

Gulfport runs on a creative, community-minded rhythm. Its downtown arts district is dense with galleries, artist studios, independent shops, and locally owned restaurants and cafés, and the city has earned recognition for its dining scene. The Gulfport Casino, a National Register-listed ballroom on the waterfront, hosts community dances and events. Residents move easily between the arts district, the marina, and the bayfront parks, often on foot or by golf cart. The result is a walkable, sociable small town that offers an Old Florida alternative to the faster pace of neighboring St. Petersburg while keeping the amenities of the larger metro area close at hand.

Public schools in Gulfport are part of Pinellas County Schools, one of Florida's largest districts. Students are served by a network of elementary and middle schools in the southern part of the county, with Boca Ciega High School located in Gulfport itself. The district offers a range of magnet, fundamental, and career-focused programs that families across the county can apply to, and the St. Petersburg area is also home to a number of private and parochial school options.

Gulfport sits just southwest of downtown St. Petersburg, with Gulfport Boulevard and 49th Street South as its principal corridors. Those routes connect residents to central St. Petersburg, the Gulf beaches, and the wider regional road network, including Interstate 275 and access to the Tampa Bay area's bridges and airports. The city's compact, flat, walkable layout makes it practical to get around locally on foot or by bicycle, while commuters to St. Petersburg, Clearwater, and Tampa are within a short drive.

Water defines recreation in Gulfport. The city's beachfront parks and beach recreation complex on Boca Ciega Bay offer open waterfront access for swimming, sunsets, and casual gathering. Clam Bayou Nature Park, adjacent to the city-owned marina, protects a brackish estuary with trails and observation decks where visitors watch wading birds, dolphins, and manatees. The municipal marina serves boaters, while the city's recreation center and fields host programs and after-school activities. The town's walkable arts district and waterfront make many of its attractions reachable without a car.