Key West Hotels

The Ocean Key resort sits at the very top of Duval Street on one side and the lively Sunset Pier on the other, making it a convenient home base from which to explore. The décor is fittingly perky—with pops of turquoise and rattan accents scattered throughout the rooms; the on-site restaurant, Hot Tin Roof (killer sunset-watching spot); and the rooftop pool—but just enough so as not to be overwhelming.

This is a big, beautiful, Deco-style resort that somehow manages to strike a balance between the glitz of a Waldorf Astoria property and local clout: The structure has been here since the ’20s and is listed on the National Register for Historic Places. The massive, 300-plus-room compound sits on a private beach, so you can retreat to a lounge chair, or your beautifully appointed guest room, or the world-class spa whenever the craziness of Duval Street, which is walking distance from the hotel, gets to be too much.