First Chair Vacations is a family of handpicked beach homes on Florida's Gulf Coast, run by Matthew, a local host who believes experiences matter more than things. From waterfront pool houses with docks, kayaks and golf carts in Indian Rocks Beach to cozy king-bed bungalows a five-minute walk from the sand, every home is set up so the vacation starts the moment you arrive: beach chairs and towels waiting at the beach-town homes, espresso machines stocked, pools heated. With more than 670 guest reviews averaging 4.96 stars, plus paddle board rentals delivered from Madeira Beach to Clearwater, First Chair makes it easy to live like a local on the beach.