Gloria Estefan — Miami Beach Hospitality Queen

Estefan and her husband Emilio own multiple properties on Miami Beach's Ocean Drive — including the iconic Cardozo Hotel (an Art Deco landmark), Larios on the Beach restaurant, and Estefan Kitchen. The Cardozo is where they filmed scenes for The Birdcage. Rooms start at $300/night with direct beach access, outperforming the average Miami Beach hotel price of $250/night by 20% for a premium oceanfront stay. Estefan Kitchen serves Cuban comfort food (the ropa vieja is legendary) for $20-40 per plate, making it 15% cheaper than the typical rival Cuban restaurants in South Beach. The Estefans have invested over $100 million in Miami Beach real estate. Gloria didn't just sing about Miami — she bought a significant chunk of it and turned it into a hospitality portfolio.