7 Stylish Hotels on the Ocean to Ring in the 200th Anniversary of Key West, Florida

Key West, Florida, is well-known for its sunny atmosphere, but not so much for its history. And Americans tend to flock to places whose main attraction is their rich backstory. Boston, which is nearly 400 years old, Philadelphia, and even the nation’s capital, are cities held in such high esteem because they’re geographical relics of the foundation of the United States. After all, there’s an undeniable thrill that comes with running a finger down the crack of the Liberty Bell. And even though America and its most historic cities are relatively young compared to their international counterparts, which were settled thousands of years ago, their anniversaries are still significant. Case in point: Key West, Florida, the two-mile-wide island that floats halfway between the tip of Florida and Havana, Cuba, is celebrating its bicentennial throughout March.

Unlike its historic neighbors in the north, Key West is a bit more of an obvious destination, courtesy of the weather. Perhaps that’s why there are so many luxurious hotels situated along the azure-hued water. For those looking to celebrate the tiny island’s 200th anniversary, be sure to do so in style at any of these seven hotels.

The Reach Key West, Curio Collection by Hilton

Positioned on the only natural sand beach in the southernmost tip of the continental U.S., The Reach Key West has recently reemerged after a multi-million-dollar renovation. Though much of the 150-room resort has changed, its nautical name remains. Plus, it’s inspired much of the quietly luxurious spaces, including the naturally lit and airy lobby, where local artwork transforms the gallery into a gallery. Perhaps the most visually charged area of the hotel, though, is the massive patio. One of the patio’s few walls is home to the Gypsy Chicken, a large-scale mural by Cuban American muralist, street artist, and painter, David Lavernia, that reaches the top of the wall.

Another stylish space? The newly appointed oceanfront restaurant whose interiors reference a famous photo of Ernest Hemingway on a fishing trip with his family in Key West. Along with many others, the image hangs prominently on the arrival gallery wall.

Parrot Key Hotel & Villas

Though the 148 guest rooms and one-and two-bedroom suites are worth booking, the pièces de résistance are the recently refreshed standalone villas that boast their own white-sand terrace and a porch with views of the mangrove-lined salt canal. The historic property, which suffered through the 2017 Hurricane Irma and has since been fully renovated, may not be the biggest in the city, but it does have four sizable pools, which means there’s no need to head down there too early to snag a lounge chair as there are plenty.

The Marker Key West Harbor Resort

Among other activations, The Marker is celebrating the city’s big birthday with cocktails—specifically, the Two Double Oh Martini. Like a few of its neighbors, The Marker is nestled within a quiet enclave near the harbor, but it’s not so isolated. In fact, it’s only a few blocks away from the energetic Duval Street, which is flanked by buzzy restaurants. Otherwise, stay put at the 96-room hotel and roam its tropical gardens and three pools, both of which are spread across the property’s two acres.

Casa Marina Key West Resort, Curio Collection by Hilton

Another hotel in Hilton’s coveted Curio Collection, Casa Marina, first opened its doors on New Year’s Eve in 1920. The brainchild of American railroad tycoon Henry Flagler, the 311-room resort was designed and built to accommodate wealthy customers of Flagler’s Overseas Railroad, which connected the little island to the Florida mainland. If the regal hotel’s architecture looks a bit familiar, that’s because the architects responsible were also behind New York City’s Metropolitan Opera House and the New York Public Library. 

And Flagler, who died before the hotel broke ground in 1918, purchased six and a half acres and 1,200 square feet of beach for the handsome price of $1,000 to offer a sense of natural luxury to his future guests, which included quite a few celebrities. Everyone from Gregory Peck to Rita Hayworth has booked a suite at the Casa Marina.

Opal Key Resort & Marina

Situated right on the Old Town Key West waterfront, just steps from the famous Mallory Square, the 178-room Opal Key Resort & Marina takes a cue from the surrounding bright blue ocean just outside. Nearly all of the spaces, whether it’s the two-bedroom suites or the alfresco bistro, feature an easy-on-the-eyes blue and white palette. Few places have more coastal-inspired interiors than Opal Key.

Oceans Edge Resort & Marina Key West

Though many hotels in the Florida Keys boast privacy, Oceans Edge, completely surrounded by crystalline waters, is as secluded as resorts can get. Luckily, the 20-acre hotel uses its water accessibility to its advantage, offering a 165-slip full-service marina and a waterfront resident restaurant that serves daily catches. Plus, Yellowfin Bar & Kitchen will even cook up your own fresh catch. And the rooms are just as much of a feast (for the eyes) as the menu items in the restaurant. Decorated in a contemporary coastal look, each of the rooms, whether a three-bedroom suite or a two-queen guest room, has a fully furnished balcony with views of the nearby Atlantic below.

Eden House

Known affectionately among locals as Key West’s original hotel, Eden House has taken a slightly different approach design-wise. It’s a circa 1924 Art Deco marvel first called Gibson Hotel, named after the original owner. The current owner, Mike Eden, promptly renamed the landmark hotel and added the surrounding historic conch houses to the property. To say Eden House is simply charming is an understatement; it’s a magnificently restored survivor of perhaps the most beloved design movement.

Pier House Resort & Spa

A 50-room boutique hotel built at the height of the midcentury modernist movement, Pier House Resort & Spa is backed by decades of history. It was actually built by a Key West native, David Wolkowsky, who’s largely credited with preserving Key West’s architectural integrity. That coveted and authentic nod to island living has attracted such luminaries as Jimmy Buffett and Bob Marley, who spent the early days of their careers in the hotel’s funky Chart Room Bar. Even American novelist Truman Capote has spent a bit of time within Pier House’s storied walls. In fact, he spent most of his winters in one of the suites while he wrote his 1986 Answered Prayers.