Mallory Square / Top of Duval

Ocean Key Resort and Spa

★★★★★

Ocean Key's address says it all: 0 Duval Street, the precise point where the island's main street meets the harbor, next door to Mallory Square. For travelers who want to be in the middle of everything — sunset on the doorstep, Duval's bars a few steps away, the Historic Seaport a short stroll east — there is no more central hotel on the island. The resort has about a hundred rooms and suites, each with a private balcony, many looking straight out over the Gulf harbor toward Sunset Key, and the property finished a comprehensive renovation in 2025 that refreshed the rooms, rebuilt the lobby with the new Sweet Bird Bar, updated the SpaTerre spa, and created the LIQUID pool lounge around the oceanfront pool for registered guests. The signature amenity is the Sunset Pier, a long open-air bar and deck jutting into the harbor with live music every day of the year — locals and visitors alike treat it as Mallory Square's grown-up alternative, with drinks in hand and the same horizon, and hotel guests have it at their feet. Hot Tin Roof, the resort's restaurant, does upscale dinners with harbor views; SpaTerre offers Balinese and Thai-inspired treatments. The trade-offs are those of any center-of-town hotel: the harbor end of Duval is lively late into the night, rates are among the highest on the island, and there is no beach — the pool and pier are the waterfront here. For a first visit focused on sunsets, walking, and nightlife, it is the strongest location in Key West.

The resort occupies one of the island's most historic waterfront parcels, where the harbor trade once docked at the foot of Duval, and its Sunset Pier was built out over the water to capture the nightly show. Its renovation has rolled out across 2025 and into 2026, with the hotel describing a refreshed property throughout — new lobby and bar, renewed rooms and baths, spa upgrades, and the pool area reimagined as an adult lounge for guests. The design leans into Key West's tropical-colonial style with contemporary polish rather than the beach-shack whimsy of some neighbors.

Choosing a room: harbor-view and oceanfront categories with balconies facing the Gulf are the reason to stay — sunsets from your own balcony, the cruise ships and schooners passing below, and Sunset Key's palms across the channel. City-view rooms look over Duval and the town and are noticeably cheaper, but you lose the hotel's best asset. Light sleepers should ask for rooms away from the pier side on weekends, since live music and the crowd below carry into the evening. Parking in this part of town is limited and costly; if you are arriving by car, check the valet arrangements, and plan to leave the car parked for the stay.

The neighborhood is the point. Mallory Square's Sunset Celebration is a minute's walk, the Shipwreck Museum and Aquarium are next door, the Conch Train and trolley depots are steps away, and the Historic Seaport's restaurants and sunset sails are a short stroll east along the harborwalk. Duval's famous bars begin at the corner. Couples on a celebration trip, sunset-chasers, and first-timers who want to walk everywhere will love it; families who want sand and calm should look south to Casa Marina or the Southernmost Beach Resort instead. Book well ahead for winter, holidays, and Fantasy Fest in late October.