The Best Hotels in Key West

Finding the perfect hotel for your Key West getaway depends upon whether you’re here for the Duval Street party or the relaxing Gulf of Mexico views. Drop your bags in the heart of Old Town or next to Mallory Square if you want to be in the center of the action; if soaking up the Conch Republic vibe is more your speed, opt for a secluded cottage on the sand.

1500 Reynolds St, Key West, FL 33040, USA
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.
725 Truman Ave, Key West, FL 33040, USA
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.
600 Fleming St, Key West, FL 33040, USA
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 the 1884 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.
501 Southard St, Key West, FL 33040, USA
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.
1 Duval St, Key West, FL 33040, USA
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.
1435 Simonton Street
Just a few blocks from the bustle of Old Town and Duval Street, this Caribbean-style resort is a serene retreat with a swath of white-sand beach, a pool concierge, and a private pier for fishing or gazing out over clear turquoise waters. All of the contemporary rooms and suites are generously sized and have private balconies with views of the pool, courtyard, or ocean, but the real draw remains right outside your door. Guests can snorkel off the shore, face off on the giant chess board, or simply sway between two palms in one of the beachside hammocks. They also have privileges at sister resort Casa Marina, just up the beach, including at the oceanfront Spa al Mare. Have kids in tow? The hotel offers a full roster of activities, plus babysitting services for parents who want to hit the town.
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