The Islands of Islamorada in the Florida Keys has the views, the amenities and the vibe of a five-star resort – without much ...

The Florida Keys compound is Portnoy's second Florida home; he also purchased a house in Miami for almost $14 million in 2021 ...

An unforgettable journey is a drive down Florida's 113-mile Overseas Highway, one of America's prettiest roads, surrounded by ocean waters that span the Florida Keys from Key Largo to Key West. While ...

Dave Portnoy is expanding his real estate presence with a new Florida Keys residence, and breaking records while doing it.

We made our approach by boat in a scene that felt like it was straight out of The White Lotus — being ferried to a private island resort in the Florida Keys. On the boat with me and the other guests ...

Barstool Sports owner Dave Portnoy bought a waterfront mansion in Islamorada, setting a record for home sales in the Florida ...

Florida Keys is kicking off the fall season with new airline services, accommodations, attractions and dining experiences.

The property had been listed for $31.2 million in June 2025, the Wall Street Journal reported, and Portnoy, a Massachusetts ...

Dave Portnoy may start filming more “One Bite Pizza Reviews” in the Florida Keys. The Barstool Sports founder just purchased ...