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A weathered timber and rock jetty running into calm water at Longboat Pass at dusk

Sarasota & Anna Maria Island · 291 licensed rentals

Longboat Key vacation rentals

Photo: Gregory Urbano from St. Petersburg, Florida, USA · CC BY 2.0

Longboat Key is a long, narrow barrier island, roughly ten miles from Longboat Pass in the north to New Pass in the south, and it sits partly in Manatee County and partly in Sarasota County. One road, Gulf of Mexico Drive, runs its whole length, with Gulf-front condo buildings, resorts and golf courses on one side and bayside homes on the other.

It is the quiet island in the chain. Rentals here are mostly condos with beach access and pools, plus canal homes with docks on Sarasota Bay. You are a bridge away from both ends of the action: St. Armands Circle and Lido Key to the south, and Anna Maria Island to the north.

Things to do near your rental

  • Greer Island, often called Beer Can Island, at the north tip by Longboat Pass
  • Boating and fishing on Sarasota Bay from bayside docks
  • St. Armands Circle shops and dining across New Pass
  • Anna Maria Island beaches across Longboat Pass

Licensed by the state of Florida

291 Longboat Key vacation rentals

Every listing starts from an active state license. Owners who claim their listing add photos, rates and a direct booking link, and appear first.

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