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A Key West vacation may be more commercialized than it used to be, but this sunny island at the end of the Florida Keys is still one of the world's most recognized vacation destinations. Perhaps it's the laid-back, local sense of sun-drenched hedonism that tourists find most contagious.
Gorgeous weather, a tropical feel, and a quirky, laid-back group of beach-town dwellers.
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Although the small, mom-and-pop guesthouse is still the quintessential Key West experience, down here they have everything from old-time motels to full-service resorts. Average room rates are over $200 and in high season, anything below $125 is rare. Minimum stays may be required in some cases, especially in high season.
La Concha Crowne Plaza
Dating back to 1926 and still the tallest building in town, La Concha’s rooms are small and old-fashioned, but its...
Marquesa Hotel
Twenty-seven rooms spread throughout an idyllic compound of four houses, one from the 1880s, comprise this small,...
Little Palm Island
This five-acre private island off Little Torch Key has 28 gorgeous bungalows and two suites, superb service, beachside dining,...
Ocean Key
Looking for serious pampering in an elegant, waterfront resort? Look no further. Two quality restaurants (one serves seafood,...
Olivia by Duval
Save your pennies at this gracious guesthouse with its cute pool and poolside grill. Pastel-colored guest rooms are outfitted...
La Concha Crowne Plaza
Dating back to 1926 and still the tallest building in town, La Concha’s rooms are small and old-fashioned, but its...
Marquesa Hotel
Twenty-seven rooms spread throughout an idyllic compound of four houses, one from the 1880s, comprise this small,...
Little Palm Island
This five-acre private island off Little Torch Key has 28 gorgeous bungalows and two suites, superb service, beachside dining,...
Ocean Key
Looking for serious pampering in an elegant, waterfront resort? Look no further. Two quality restaurants (one serves seafood,...
Olivia by Duval
Save your pennies at this gracious guesthouse with its cute pool and poolside grill. Pastel-colored guest rooms are outfitted...
Hungry? Choose from Key West's 240 dining spots ranging from simple diner-style joints and old Conch hangouts to cutting-edge kitchens.
Alice's Key West Restaurant
Alice’s one-room eatery is a local institution. She cheerfully dubs her deliciously inventive fare "new world...
Blue Heaven
Live roosters wander among outdoor tables in this artsy joint and former whorehouse (Ernest Hemingway used to referee boxing...
Pepe's Café
A venerable Conch stalwart with an old-time vibe, order oysters or one of their tasty fish sandwiches in the rustic,...
Seven Fish
Check out this snug little favorite in Old Town for its quality Asian fusion cuisine – dishes include crab and shitake...
El Siboney
Enjoy the solid Cuban home-cooking – chicken and rice, tangy Cuban-style pork, paella, and island sandwich classics...
Louie's Backyard
Chef Doug Shook blends Florida, Caribbean, and world cuisine with dishes like his stew of Mediterranean fish, shellfish,...
Alice's Key West Restaurant
Alice’s one-room eatery is a local institution. She cheerfully dubs her deliciously inventive fare "new world...
Blue Heaven
Live roosters wander among outdoor tables in this artsy joint and former whorehouse (Ernest Hemingway used to referee boxing...
Pepe's Café
A venerable Conch stalwart with an old-time vibe, order oysters or one of their tasty fish sandwiches in the rustic,...
Seven Fish
Check out this snug little favorite in Old Town for its quality Asian fusion cuisine – dishes include crab and shitake...
El Siboney
Enjoy the solid Cuban home-cooking – chicken and rice, tangy Cuban-style pork, paella, and island sandwich classics...
Louie's Backyard
Chef Doug Shook blends Florida, Caribbean, and world cuisine with dishes like his stew of Mediterranean fish, shellfish,...