Best Key West Hotels

If you want to be oceanfront, this is the place to be. Rather than the chain’s normal glass-and-concrete style architecture, they went totally Key West, blending wood architectural details with railings, staircases and balconies. The central courtyard is open on one end to provide views over the harbor and hosts a large, comfortable pool. The adjacent Blue Mojito bar overlooks the pool, courtyard and harbor and has acres of outdoor seating, perfect for those steamy tropical nights. With its own private dock, gourmet SHOR restaurant, a wonderful spa and architecture similar to the Hemingway house, we simply loved it here. The bathrooms are huge, with showers that could hold half a dozen adults, and the most comfy bed we’ve ever slept on. The staff is ample and friendly, and walk three blocks and you’re standing at the intersection of Front and Duval streets. 

This used to be our favorite hotel not just in Key West, but anywhere in Florida. Built by Henry Flagler as the grand punctuation mark to his jaw-dropping engineering feat--bringing the Florida East Coast Railroad across miles of open ocean to Key West--the original building was a Gilded Age masterpiece: thick walls, exposed heart pine beams, wooden floors and a century’s worth of character. The hotel has been used as officers’ quarters in more than one war, but fell into decline after the Cuban Missile Crisis through the late-1970s, when it was restored and refurbished. It really gave a view of how the wealthy lived and played. It was acquired a few years back and “expanded,” by which the new owners meant stripping much of the character from the interior and adding on some noisy rooms in a new wing with outdoor concrete concourses. It’s now part of the Waldorf Collection and, while the service is undoubtedly superb, nothing can bring back the turn-of-the-century character of the original. It’s oceanfront, with a beautiful beach out back and a pool overlooking the ocean. If you can get past the remodel, it’s in a great location on the Atlantic end of town.

At the opposite end of Duval Street from Mallory Square, the Southernmost Hotel offers good value. It’s actually a collection of four properties, including the historic Dewey House. The Southernmost Hotel is across the street from the beach, while La Mer is on the beach. Guests at the four properties share all of the complex’s amenities (fitness center, spa, restaurants, pools, beach). This end of Duval has plenty to keep you interested, but don’t walk all the way to Front Street at the opposite end unless you have a couple of hours and comfortable shoes. Rooms are clean and kept up-to-date.