The Gasparilla Inn

14 Best Hotels in the USA, Canada, and the Caribbean 2026 According to Our Editors | Condé Nast Traveler

"A storied icon of American hospitality, The Gasparilla Inn sits on its eponymous barrier island on Florida’s Gulf Coast. The historic 1913 landmark has evolved into a vibrant pageant of old-Florida grace: an expanded 63-room inn surrounded by yellow clapboard cottages, a golf course on its own island, and a sprawling beach club that’s set amid manicured palms, bougainvillea, and banyan trees, and fronts one of the state’s most magnificent beaches. Every detail here feels correct: Interiors by Kemble Interiors showcase an exuberant mix of coastal maximalism and island whimsy. Each space looks lovingly composed, from the pink-tinged ladies sitting room and the floral-saturated main hall with its “green goddess” tones and orchids to the coral-and-cream ocean cottages overlooking the Gulf. Owned by just three families throughout its 113-year history, the Inn protects its heritage and privacy with near-reverent care. Tradition still rules here, as brass keys hang where they always have, reservations are made by phone, and loyal guests return season after season to the same beloved rooms. The Gasparilla Inn endures as the epitome of old-Florida magic: historic, timeless, and still undeniably relevant. From $470. —Paul Rubio" - CNT Editors