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North of the island

Madeira Beach.

The northern edge of our coast — boardwalks, working fishing boats, and the sunsets that keep guests coming back.
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The neighborhood

Sunsets, boardwalks, John’s Pass.

Madeira Beach has a fishing-village heart. Wooden boardwalks along John’s Pass, working boats that still leave every morning, and one of the most photographed sunsets on the coast. It is the neighborhood that pulls guests back year after year.

Come here when the trip is about slowness, seafood, and long walks by the water. The pass connects the barrier islands to the mainland by boat, and half of Madeira’s rhythm follows the boats out and back in. The other half is beach, and it covers a specific mood: John’s Pass, the boardwalks, and the sunsets over the water.

Kelly and Josh spend time in Madeira often — showings, listings, dinner at John’s Pass. If you’re staying here, ask us where the boat captains eat breakfast and which of the boardwalk shops are worth ten minutes.

The neighborhood

Where we’d send a friend.

A short list — not a directory. These are places we return to, and the ones we mention when guests ask for a recommendation.

The Friendly Fisherman

Classic seafood at John’s Pass since the 1970s. Grouper straight off the boat, family-run kitchen, and prices that never chased the tourist crowd.

John’s Pass Village & Boardwalk

Wooden boardwalks, a working fishing marina, and shops that have been here for decades. The sunset over the pass is one of the reasons Madeira has fans.

The Wharf Restaurant

Waterfront dining right on the pass. Grouper sandwich, tropical drinks, and dolphins swimming through the channel most afternoons.

Hubbard’s Marina Dolphin Cruise

Family-run since 1928. Two-hour dolphin cruise or a full-day fishing charter, all leaving right from John’s Pass. Kids come home tired and happy.

The Sunset Ritual

The reason many guests come back year after year. Public beach access at every block, kite-flyers in the wind, and one of the coast’s most honest sunsets.

Boca Ciega Millennium Park

A quiet slice of preserved wetland right on the causeway. Kayak launch, walking trails, and one of the best places nearby to spot manatees. Free, open dawn to dusk.
Where to stay

Pink Chair homes in Madeira Beach.

A few of our current rentals in the neighborhood. Each cared for by our team, each with its own personality.