Beach access is limited and largely private. Most Gulf-facing condos and homes have deeded beach access or private walkways. There are a handful of public beach access points, but these have limited or no parking, making them impractical for most visitors. When buying, it’s critical to confirm whether your deed includes beach access rights — and what those entail.

Longboat Key is known for strict rental policies. Most condo associations prohibit rentals shorter than 30 days, and many only allow rentals once or twice per year. The Town of Longboat Key also limits vacation rentals in single-family areas to 30-day minimums. This has helped preserve the quiet, residential character — but it’s essential to check each property's zoning and HOA rules before purchasing.

Longboat Key is in a Category A evacuation zone, meaning it’s among the first to evacuate during a major storm. Barrier islands are more exposed to storm surge and wind damage. While the island is well-maintained with strong infrastructure, buyers should consider storm-rated windows, elevated construction, and flood insurance requirements, even if no mortgage is involved.

• The south end (closer to St. Armands and Lido Key) is more developed and luxurious, featuring the Longboat Key Club, upscale condos, and golf course properties.
• The north end is quieter, more residential, and feels more like “Old Florida” — with older homes, fewer high-rises, and proximity to Cannon’s Marina and Mar Vista Dockside.
• The middle of the island blends both, with a mix of gated communities, waterfront homes, and convenience stores.

Longboat Key is not especially walkable unless you’re in a specific condo complex. There’s no traditional “town center,” though Shoppes of Bay Isles offers a Publix, CVS, banking, and some services. Most residents drive to St. Armands Circle or Bradenton for restaurants, shopping, and entertainment. Longboat prioritizes quiet, residential living over urban-style walkability.

There are no hospitals on Longboat Key itself. The nearest are Sarasota Memorial Hospital (south) and Manatee Memorial (north) — both 20–30 minutes away. The island does have a fire department with EMT response, and Sarasota Memorial operates a walk-in urgent care clinic off the south end, near St. Armands. Serious emergencies require evacuation to the mainland.

Traffic can be a challenge during peak season (January–April), especially at the New Pass Bridge(south) and Cortez Bridge (north). Morning and late afternoon congestion is common when snowbirds and day-trippers are arriving or leaving. Living in the middle or north end of the island may reduce reliance on the busier southern bottlenecks.

Some larger communities like Bay Isles, The Longboat Key Club, or Country Club Shores have active HOAs with fees covering security, landscaping, and amenities. Beyond that, the Town of Longboat Key collects taxes and manages utilities such as water and sewer. There are no CDDs (Community Development Districts), but condo association fees on the island can be higher than average.

Longboat Key has a reputation as a luxury retirement destination, and the average resident is older than in most Sarasota communities. That said, you’ll find a growing number of remote-working professionals, seasonal families, and boating enthusiasts drawn by the privacy, Gulf access, and refined lifestyle. There are no schools on the island, which discourages full-time family residency.