Book Cheap Last-Minute Hotels in Key West

Here’s the biggest thing to know about the country’s southernmost city—Key West is the definition of “on island time.” Maybe because it’s basically happy hour 24/7 here. Is it Wednesday or Saturday? Who cares! Grab another daiquiri.

In a town of endless summers and countless free spirits, creating a hard-and-fast itinerary is a no-go. Once you’ve booked one of the best hotels in Key West, there are the basics to cover: meandering down Duval Street and popping into the renowned Sloppy Joe’s, catching an unreal sunset at Mallory Square, and eating your weight in locally caught shrimp, crab, and conch. After that, the untamed sky’s the limit, but here’s a footloose and fancy-free guide to this two-by-four-mile island, because there’ll be no wasting away in Margaritaville while you’re here. (Okay, maybe a little.)

Welcome to the Wild, Wild Key West

Go All the Heming-way: Ernest Hemingway is often misquoted as saying, “Write drunk, edit sober,” so he may have also said, “Key West is bomb.” No one can know for sure. But one thing is certain—this is a Hemingway-centric town. Stopping by the home where the novelist wrote most of his works is mandatory for one reason: The pack of 40 to 50 six-toed Hemingway cats. Next, grab some blueberry pancakes for breakfast at Blue Heaven and honor the garden grounds of where the author used to referee boxing matches.

Get Nauti(cal): Your last-minute getaway to Key West does have to get a little beachy at some point. Especially when you have so many enticing options to get wavy. This is a diving and snorkeling paradise and getting into the turquoise waters is a must. If you’d rather stay dry, hop on a boat for a sunset sail (sunsets are huge here), or grab a kayak or paddleboard and skim through the mangroves.

Lime Time: Key West is home to the key lime, which is the tarter sister to a regular ol’ lime. So, when in the Keys, do as the Floridians do—eat a big slice of key lime pie. The master of the tasty pastry here is Kermit’s Key West Key Lime Shoppe, where you’ll also find all other forms of the tart stuff, from marinade to dog treats. To get your sips with a side of lime, cozy up to the bar for a Sloppy Rita at Sloppy Joe’s or a Key Lime Mojito at Willie T’s. After you’ve out-limed yourself, squeeze your way back to your Key West hotel near Duval Street to unrind.

Heed the Call of the Oddball: There’s definitely a weird side to Key West. This is the town that once mock-threatened to secede from the nation to become “The Conch Republic,” after all. So if you’re ready to get uncanny, there’s plenty of opportunity. The Garden of Eden is a “clothing optional” rooftop bar where you can let it all hang out, while Captain Tony’s Saloon is the oldest bar in Florida and the site of a former gallows (the tree is still in the center of the bar), as well as a morgue, bordello, and cigar factory. Even Key West’s above-ground cemetery has a twist. You’ll find tombstones engraved with dark humor from beyond, like “I told you I was sick” and “I’m just resting my eyes.” This wacky jaunt is sure to cause you to want to give your own lids a break, so get some shut-eye at your Key West hotel near Mallory Square.

Frequently Asked Questions About Key West