Duval Street is the legendary spine of Key West's entertainment district, a mile-long strip from the Gulf to the Atlantic packed with bars — most famously Sloppy Joe's, Hemingway's favourite — dive bars, drag show venues, souvenir shops, and restaurants that collectively create the most uninhibited and festive street atmosphere in Florida. The Sunset Celebration at Mallory Square at the western end is a daily ritual of street performers, musicians, and sun-worshippers gathering to applaud the Gulf sunset. Hotels near Duval Street in Old Town Key West are at the heart of the Conch Republic's legendary nightlife.
Our Picks — Key West
Old Town
Key West's finest full-service waterfront resort sits at the foot of Duval Street with a private dock, sunset-view pool, and 100 suites facing the Gulf of Mexico — the preferred address for those who want resort facilities without sacrificing the soul of Old Town. The rooftop Hot Tin Roof bar is one of Key West's best sunset perches.
Key West Harbor
A modern boutique resort on the harbor designed with a zero-waste philosophy — solar panels, electric boat charters, and a marine conservation partnership — without sacrificing any luxury amenity. Three pools, a water sports center, and 96 rooms with harbor views make it Key West's most thoughtfully conceived newer property.
Old Town
Key West's most romantic address — a collection of four historic buildings connected by half an acre of private tropical gardens with a freshwater pool, koi ponds, and a 60-year-old bronze orchid collection. The 17 rooms are individually furnished with antiques, and the absence of TVs is a feature rather than an oversight.
Old Town
A Key West institution since 1968, anchoring the corner where Duval Street meets the Gulf with a private beach, full-service spa, and 142 rooms ranging from poolside cottages to Gulf-view balcony suites. The Chart Room bar — a wood-paneled mariner's bar that hasn't changed in 50 years — is where every Key West visit should begin.
South Beach
Key West's most family-friendly full-service resort, straddling Atlantic and Gulf beaches at the island's southern tip with three pools, a poolside tiki bar, and direct access to both Southernmost Beach and the Atlantic. The rooms in the Beach House are the finest, with private balconies facing the water.
Old Town
One of Old Town's best-priced boutique options — a restored 1895 Conch House with 13 rooms, a plunge pool, and free beach cruiser rentals, all two blocks from Duval Street. The genuine B&B warmth, owner-operator hospitality, and extraordinarily central location make it one of Key West's best values.
Looking for more options? See all Key West hotels