The southernmost island in the always-popular Florida Keys, Key West may also be the archipelago’s boldest. It’s a tropical favorite for divers, beachgoers, snorkelers and swimmers, thanks in part to the miles of coral reef you can explore. As the marine life is diverse, so are the people, and a rich nightlife attracts partiers to Key West. Surrounded by Caribbean architecture, it’s no wonder famous artists and writers (like Ernest Hemingway) decided to reside in its supremely chill vibes. Add in fresh seafood and Cuban coffee and cigars and you have a (very) abbreviated idea of what Key West can offer.
Yes, there’s plenty to do in Key West, and chances are you won’t be spending too much time in a hotel room when you can lounge on the area’s sparkling white sand. So instead of spending time indoors, why not choose a hotel with easy beach access from our list below?
From $800/ night
Yes, they’re expensive, but the Sunset Key Cottages comes with a reason for their exorbitant price tag. The entire property is located on a 27-acre private island (the eponymous Sunset Key) but 500 yards from Key West. Cottages contain up to four bedrooms, with kitchens, verandas and a TV included, making them a hit with families. But Sunset Key is also beloved by couples apparently: the on-site restaurant Latitudes has been ranked among OpenTable’s “100 Most Romantic Restaurants.” Enjoying a meal with your significant other on a private island, overlooking a sparkling abyss of blue? That’s so romantic it’s almost cliche!
From $226/ night
The glowing, fairy-tale exterior of this beautiful property looks like something out of Alice in Wonderland—too bad the kids can’t enjoy the inside, as it’s an adults-only hotel. Hopefully those of-age can still find time to enjoy the tropical palettes and cozy furnishings of this bed and breakfast. Located on the popular and busy Duval Street, the 18 elegant guest rooms here offer air-conditioned, wifi-equipped bliss—and the promise of a complimentary breakfast once morning comes. The beach (and a zero-entry pool) are also but steps away from this gorgeously redone Victorian building.
From $263/ night
Key West is known for its party atmosphere, and after a night out you may want to rest your head without screaming kids nearby. Sorry children, but sometimes your parents need a little alone time and so this is the second adults-only property on our list. The real reason for its inclusion, though, is its abundance of favorable reviews (almost a perfect 10 on Booking). It’s close to Duval Street if you want to shop or dine, while the hotel itself offers a little rooftop fun with a year-round pool and sun terrace. Rather stay in your room than possibly socialize with people? A complimentary happy hour and drink upon arrival should help loosen those nerves!
From $179/ night
Walk outside your room here and white sand will be nearby. This oceanfront resort is as colorful and cultured as Key West itself, and its interiors blend midcentury design with Havanan motifs and colors. The active-bodied should enjoy themselves, with distractions as numerous as kayaking, birdwatching (parrots included!) and LED-lit paddleboarding. All rooms come with refrigerators and seating areas—giving you plenty of space to pour yourself (and a few friends) a nightcap before bed. You might even be able to enjoy that drink with nighttime scenery: many rooms come with views of the courtyard or ocean.
From $117/ night
Yes, the Southwinds Motel is our value option for Key West—but oh, what value it brings. Only a block away from Duval Street, this motel is a walker’s paradise, with 37 restaurants less than a half-mile away. Butterflies, liquor and an art gallery are also within a 4-minute walk, further proving just how sweet and diverse a location this is. The rooms are minimal but comfy, and past guests have been positive with their feedback. Southwinds’ proximity, friendly staff and reasonable prices croup up consistently in reviews. But wait, there’s more: like free breakfast (highly rated by guests), as well as a pool and bike rentals you can enjoy during your stay.