Of all the islands threading out from Miami that make up the Florida Keys, Key West is by far the edgiest and most frequented—for a reason. Its seven square miles are a tropical oasis of classic Caribbean homes in pretty pastels, wild mangroves, sugar-white beaches, and a spirited, laid-back local ethos that keeps the party going from dawn to dusk. Want in on the action (or lack thereof)? Check into one of the island's best hotels.
The Perry Hotel
This isn’t your average beachside hideaway. The Perry Hotel, the latest to hit Stock Island, is all about contemporary design (think natural wood floors and stone-gray walls) and, thanks to a horseshoe-shaped layout, marina views from each of its 100 rooms and their private terraces. On site, you’ll find an oyster bar, distillery, “boat-to-table” restaurant (think Key West pink shrimp and chilled Florida lobster), and art gallery with rotating exhibits. If that’s not enough culture for you, a free shuttle is available to bring guests downtown.
While The Gates’ address in New Town (about 20 minutes’ drive from downtown’s restaurants and shops) leaves much to be desired, there’s still lots to love. Guest rooms exude a serene beach house vibe, with their whitewashed wooden beds, leather club chairs, and seascape photography by local artist Jorge de la Torriente. Another highlight: the buzzy pool scene, where the Rum Row bar hosts live music and weekend DJs and The Blind Pig food truck churns out “conch fusion” small plates including tacos and ceviche.
Ocean Key Resort
Do you prefer a city view or an ocean view? At Ocean Key Resort, you can take your pick: all 100 guest rooms have balconies overlooking either the ocean or historic Duval Street, Key West’s main drag lined with early Victorian architecture, independent art galleries, bed and breakfasts, and bodegas. Rooms are contemporary, with the added luxury of whirlpool tubs, but the biggest draws are elsewhere. Downstairs, a waterfront pool features a hot tub and cabanas, SpaTerre incorporates oils and clays from Bali and Thailand into its treatments, and the pier-side restaurant features nightly music and dancing alongside perfect sunset views.
Despite being just a few blocks from frequented Old Town, Pier House manages to feel like its own private island. The former harbor-front motel is now a 142-room retreat, its low-rise buildings surrounded by bougainvillea and decorated Old Key West style with tropical prints, colonial furniture, and local art. After checking into your room (the best have balconies overlooking the Gulf), stop by the Chart Room Bar—where Jimmy Buffet and Bob Marley got their start—and fuel up on hot dogs and free popcorn before hitting the small but private white-sand beach.
Sunset Key Cottages
If only a real private island will do, set your sights on Sunset Key Cottages. A seven-minute ferry shuttles guests from Key West proper to the 27-acre Sunset Key, where just 40 pastel cottages are surrounded by palm trees, tropical gardens, white-sand beaches, the turquoise-blue ocean, and nothing else. Every room is full of charm—think bold yellow and blue accents and floral prints—as is breakfast, delivered via picnic basket straight to your porch. Factor in pampering spa treatments and romantic beachfront dinners at Latitudes Restaurant, and you might never want to leave.
Casa Marina Key West
It doesn’t get more glamorous in Key West than Casa Marina, a 1920s-era Art Deco landmark designed by the same architects as the New York Public Library that’s welcomed everyone from Rita Hayworth to Gregory Peck. Expect tech-savvy amenities, aromatherapy and oxygen facials at the spa, and a rum-focused cocktail bar. What remains blissfully unchanged? The butler-attended private beach—Key West’s largest at 1,200 square feet—remains as exclusive as ever.
It’s no longer Key West’s newest place to stay, but when it opened near the Seaport in 2014, The Marker signaled the area’s first new-build hotel in over two decades. The hotel's conch-style architecture (think sloping roof lines and covered porches) nods to its Key West roots; inside, the 96 rooms are more fashionable with their patterned carpets and armchairs and backlit mirrors. Despite the hotel’s relatively small size, there are three pools to splash around in (including one for adults only) as well as a poolside bar that hosts tequila tastings. The breezy Cero Bodega restaurant is a solid choice for lunch, where you can enjoy Cal-Mex cuisine (Cuban pork wraps; avocado salads) with waterfront views.
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Stock Island, set away from the buzz of downtown Key West, sets a sophisticatedly quiet tone for Oceans Edge, the area’s largest resort. All 175 ultra-spacious rooms have porches or balconies looking out at the ocean—a theme echoed inside in the form of driftwood lamps, navy blue and white linens, and framed tropical prints. Choose from a whopping six heated pools (all accompanied by loungers and canopy beds) to get your tan on. Rather arrive by yacht? The resort has its own private marina, where charters leave for fishing and diving excursions in the Dry Tortugas.