The 36 Best Places to Drink and Stay in Key West

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Three pools, a harbor view, and the kind of tropical-modern design that manages not to embarrass itself in a town where novelty is usually suspect. The Marker is a waterfront resort on the quieter edge of Key West, and its neighbors, famously hostile to anything new, seem to have made peace with it. Rooms lean into the Caribbean palette without overdoing it, and the water is right there, which in Key West is really the whole point.

1. Forbes Travel Guide Forbes Recommended
2. AAA Three Diamonds

A cluster of 19th-century conch houses stitched together into a 44-room boutique hotel, the Kimpton Fitch Lodge barely looks like a hotel from the street, which is half the point. The residential scale keeps things unhurried, and the outdoor pool, loaner bikes, and a nightly hosted social hour keep them social. It sits just off the waterfront, making diving, sailing, or ferry departures easy to reach without much planning.

1. AAA Three Diamonds
2. Michelin Guide Selected Hotels

A cluster of 19th-century buildings spread across half a city block, the Lighthouse Hotel sits next door to its namesake and directly across from the Hemingway house, which is either a selling point or a lot of literary pressure. Rooms go tropical-classic, with vintage-inspired prints and furniture alongside modern comforts. The grounds wind around an old banyan tree and pool, and the bar pours a Hemingway-inspired mojito, as one must.

1. AAA Three Diamonds
2. Michelin Guide Selected Hotels

Sitting at the southernmost tip of the continental United States, this beach resort straddles the turquoise Atlantic and Key West's chaotic Duval Street, which is either perfect or a lot, depending on your evening plans. A midcentury overhaul swapped tired tropics for cobalt, coral, and woven rugs on wood floors. The adults-only guesthouses, set in a pair of restored Victorians next door, are the quieter bet.

1. AAA Three Diamonds
2. Michelin Guide Selected Hotels

Named for maritime painter Winslow Homer, this collection of historic houses spreads across Key West's old district with three swimming pools and a poolside Bungalow Bar tying it all together. The rooms mix contemporary interiors with the buildings' original bones, and the common outdoor spaces are generous enough that you'll forget you're in the middle of town. The Michelin Guide has it among its selected hotels.

1. AAA Three Diamonds
2. Michelin Guide Selected Hotels

Stock Island sits close enough to Key West that the distinction feels bureaucratic, which is roughly how the Perry Hotel gets away with being the freshest place to stay in a neighborhood that almost never builds anything new. The marina-side hotel has the bones of a well-designed resort without the theme-park finish, and Architectural Digest flagged it on arrival. A good base for people who'd rather dock a boat than fight for parking.

1. AAA Three Diamonds
2. Michelin Guide Selected Hotels

1. Michelin Guide 2 Keys

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Three Diamonds

1. AAA Four Diamonds

1. AAA Approved

1. AAA Approved

1. AAA Approved

1. AAA Approved

A 24-acre resort on a stretch of the Keys most people blow past on the way to Key West, Isla Bella sits near the east end of the Seven Mile Bridge with five pools, a sandy beach, and nearly 200 suites. It's a self-contained luxury resort, the kind where you could theoretically never leave the property, which for some people is a vacation and for others is a warning.

1. Michelin Guide Selected Hotels

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