"Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments."

"With a large grass lawn set for farm-table dinners and celebrations, The Gates is a different kind of Key West resort that owes more to Brooklyn than Margaritaville. In keeping with the hipster vibe, the hotel’s only restaurant is the Blind Pig food truck, which is permanently parked outside near the pool and serves breakfast goodies, tacos, and sandwiches from morning until late, and(for reasons unknown) the last line of The Great Gatsby, done in a shticky nautical pastiche, hangs over the counter at the open-air Rum Row pool bar. Shiplap walls and headboards in the rooms are the definition of millennial chic—and Instagram gold—as are the wooden docks for tablets and smartphones."

"Key Lime Inn Both charming and affordable (it doesn’t charge a resort fee), this intimate 37-room property also has an unbeatable central location—near the heart of Old Town and just a few blocks from Duval Street and Mallory Square. Part of the Historic Key West Inns collection, the Key Lime Inn features classic Key West style with a 19th-century main house highlighted by a double-height colonnaded entrance and green shutters. Rooms follow suit with high ceilings and classical proportions, and beds are done up in crisp, white linens; most have sitting areas and private walkouts or porches to encourage lingering. Though short on amenities, the grounds are shaded by tall palms and dotted with Caribbean-style clapboard cottages painted in cheery colors with gingerbread trim, and all offer free WiFi. And if the beach doesn’t call you, a large wood deck surrounds the heated outdoor pool, and hammocks and porch swings are placed around the property for maximum relaxation."

"Located on Fleming Street in the heart of Old Town Key West , the Marquesa has everything you might expect from a romantic coastal-Florida retreat. Wide porches overlook lush gardens and a bijou pool at the center of the complex, and brick paths shaded by large palms and tropical foliage give the1884 Greek Revival–style property a secret hideaway feel. It’s understandable if you want to hole up in the guest rooms, which reside in traditional clapboard conch houses and are furnished with an eclectic collection of wood pieces sourced from around the world. In 2018, Marquesa 4-1-4 opened across the street, featuring a new compound of three buildings around a central swimming pool and courtyard. After a day spent exploring nearby Duval Street, make your way back to Café Marquesa, which is perennially packed with locals and visitors enjoying fresh seafood and an inventive menu."

"Right on Key West’s famous Sunset Pier and next to Mallory Square, Ocean Key is at the center of the action, proven by the flocks of tourists who descend on the pier every evening at sundown. Inside the resort, the contemporary rooms are decorated in tropical colors like bright lime and turquoise, and have bathrooms with rainfall showers and whirlpool tubs and private balconies with views of the Gulf of Mexico or buzzy Duval Street. The angular pool is surrounded by cabanas and day beds; grab a ringside seat for the daily fashion show at Liquid, the kicking poolside bar. Prefer a quieter experience? The spa has a full range of treatments and packages that lean heavily on Asian traditions and ingredients, from Balinese massage to a Javanese rice-and-turmeric body scrub."

"Set at the end of Duval Street, near Sunset Pier and Mallory Square, Pier House takes advantage of its waterfront address with three tiers of balconies and a pocket-sized stretch of private beach. Its location means guests are within walking distance of all of Old Town’s highlights, from the Clinton Square Market to the Harry S. Truman Little White House. Many come to follow in the footsteps of the mayor of Margaritaville himself, Jimmy Buffet, who played his first gig in town in the hotel’s now infamous Chart Room Bar. Order a rum runner, then head to the heated outdoor pool; though it’s on the small side, it has sweet views to Key West Bight. After an adventure-packed day, the rooms and suites offer low-key comfort, decorated with traditional furniture and local art and overlooking the ocean or tropical gardens and koi ponds. Equally serene is the full-service spa,one of the few on Key West."

"In its previous lives, the pink turreted Southernmost House was a private home, nightclub, and residence for visiting dignitaries, but the Queen Anne mansion is now an adults-only B&B that brims with unexpected history. Built in 1896 by a wealthy Florida family, the electricity was put in under Thomas Edison’s supervision and the club attracted Louis Armstrong, Tallulah Bankhead, and Tennessee Williams; the hotel has also hosted five U.S. presidents as well as the king of Spain . Today, guests will enjoy its location at the quiet end of Duval Street, not far from the green gardens and six-toed cats of the Ernest Hemingway Home and Museum and just a block from the southernmost point of the continental United States marker. The classical lobby and public areas are filled with ornate antique furniture, and uniquely decorated rooms have four-poster beds and antique Oriental rugs. Snag a lounge chair near the Atlantic-facing swimming pool, then meditate on your own past lives under the blazing sun."

"Key West may be the southernmost point in the continental United States, but one step farther you’ll find Sunset Key, an islet just a few minutes across the harbor. Only guests and those with reservations at the resort’s Latitudes restaurant can take the private boat launch there, ensuring serene seclusion. Narrow lanes lined with clapboard cottages give the resort a residential feel, as do wide porches dotted with white, wooden rockers and gardens planted with bright tropical blooms; all have kitted-out kitchens, flatscreen TVs, and WiFi that extends to the verandahs. Spring for a four-bedroom, oceanfront cottage with private plunge pool, or simply set up on a day bed on one of the white-sand beaches that fringe the island. Sundown is the hardest time to get a dinner reservation at Latitudes, but you can still catchfiery hues lighting up the sky later into the evening."