Key West has never been a place that asks you to tone it down. The southernmost island in the Florida Keys — self-styled 'Conch Republic' — welcomes roosters in the streets, costume-heavy nights on Duval Street, and anyone who'd rather claim a poolside lounger than a barstool. Jimmy Buffett fans already know the lore: he reportedly finished writing 'Margaritaville' while stuck in traffic on the Seven Mile Bridge and debuted it on Duval Street not long after. That anything-goes energy peaks during Fantasy Fest, the island's big annual party, but the default setting here is simply warm, sunny and unbothered.
So where should you actually sleep? The short answer, according to a recent roundup of the island's best hotels from Condé Nast Traveler: aim for Old Town. This historic quarter at the island's western edge fronts both the Gulf of Mexico and the Atlantic, and nearly everything worth doing — great restaurants, Hemingway-era sites, scruffy dive bars — sits within a short walk. It's the kind of place where a post-dinner wander through leafy, gingerbread-trimmed streets is part of the holiday, not a commute.
The counter-argument is price. New Town, further east, has more conventional accommodation, often at noticeably lower rates. What you trade away is atmosphere: think chain-mall parking lots and shuttles timetabled by the hour. Given that so much of Key West's appeal is stumbling home past lush gardens after an evening out, the editors' advice to splurge on Old Town — ideally in one of the restored cottages or historic buildings where the island's literary and seafaring past is still visible — is hard to argue with.
The hotel picks span the whole spectrum of Key West holidays. There are historic inns for couples after romance, lively options suited to a friends' weekend, adults-only properties serving the island's long-established LGBTQ and clothing-optional scene, family-friendly beach resorts, and even stays on private islands offshore. The common thread is that each property was reviewed by a journalist who has actually visited, with selection based on design, location, service and sustainability credentials across a range of price points — so the list works whether you're booking a honeymoon or a budget-friendly group trip.
For travellers, the takeaway is simple: Key West rewards staying central. Book an Old Town property early if you're targeting festival dates or winter high season, and expect to pay a premium for the walkability and heritage factor. If budget wins, New Town is a workable fallback — just factor in the back-and-forth to the fun.
Full write-up at Condé Nast Traveler.