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Where to stay on Florida's Gulf Coast: small inns, guesthouses and beach towns

Florida's Gulf Coast has low-rise beach towns, sunsets over the water and plenty of small, owner-run places to stay. Here is how the main stretches compare, from St. Pete down to Naples.

Anna Maria Island

Anna Maria Island is three small cities on one barrier island: Anna Maria at the north end, Holmes Beach in the middle and Bradenton Beach to the south. Each city caps building heights, so the island has a low-rise, old-Florida feel.

A trolley runs the length of the island every day from about 6am to 10:30pm, between Coquina Beach and the Anna Maria City Pier, so many visitors leave the car parked. The historic City Pier, first built in 1911, was rebuilt after the 2024 hurricanes and was expected to reopen in fall 2026; check its status before you go.

Siesta Key

Siesta Beach, just southwest of downtown Sarasota, is known for its fine, white sand, which is about 99% quartz and stays cool underfoot. Crescent Beach, further south on the key, has the same sand.

St. Pete and Pass-a-Grille

St. Petersburg combines a downtown with museums, including the Dalí Museum, and Gulf beaches nearby. Pass-a-Grille, at the southern end of St. Pete Beach, is a historic district listed on the National Register of Historic Places. Fort De Soto Park, run by Pinellas County, has beaches, trails, a historic fort and kayak and canoe trails.

Sarasota

Sarasota is home to The Ringling, the John and Mable Ringling Museum of Art, and it is the mainland base for Siesta Key.

Naples

Naples has a long Gulf beach. The Naples Pier is closed while it is rebuilt, with completion targeted for July 2027, but the beach stays open from the Broad Avenue South and 13th Avenue South beach ends.

Why choose a small inn or guesthouse

  • You often deal with the owner or a small team who know the area.
  • You can ask questions before you commit.
  • When you book direct with a property, you pay the property.

When to go

Winter and spring are the busiest months, so book early. Atlantic hurricane season runs from June 1 to November 30, so read the cancellation terms before you book a summer or fall stay.

Plan your stay

Ask ChatGPT or another AI assistant for a small inn in the area, or search bookd.direct, where independent properties list directly and you pay the property.

Also see: Where to stay in the Florida Keys

Details checked against public sources in October 2026. Opening times, prices and closures change, so check with each place before you travel.