Atlantic Side / South Old Town

The Reach Key West, Curio Collection by Hilton

★★★★★

The Reach is the beach resort for people who want to walk to Duval. It sits at 1435 Simonton Street on the Atlantic side of Old Town, on what the resort describes as one of Key West's only natural sand beaches — a real distinction on an island where most beaches are built with imported sand. From the lobby, the southern end of Duval Street, the Butterfly Conservatory and the Southernmost Point replica are a few minutes on foot, and Mallory Square is a pleasant twenty-minute walk or a short bike ride. The resort was renovated and relaunched as part of Hilton's Curio Collection in 2020, and it is a sister property to Casa Marina, a short walk along the shore, which broadens the choice of pools and restaurants for guests. Rooms and suites are bright and coastal, many with balconies and ocean or garden views. The beach is the main event: loungers and cabanas on the sand, paddleboards and kayaks for rent, watersports operators on site, and a calm, shallow shoreline. The pool has a shallow end for children and a poolside bar, and Four Marlins serves oceanfront breakfast, lunch and dinner. A spa offers massages and treatments by appointment. The resort is dog-friendly, with a playful yappy hour for pups. Trade-offs: rates are high in season and resort and parking charges add up; the beach, while natural, is small and the water is shallow with seagrass, so do not expect a long Caribbean strand; and the ambience is relaxed rather than glamorous. For families and couples who want sand, a pool and Old Town within walking distance, it is one of the best-balanced stays on the island.

Why stay here rather than on Duval: you get a genuine resort day — beach, pool, a drink at the bar — and can still walk into town for dinner without a car or taxi. The Atlantic side of the island is quieter, with mostly residential streets and guesthouses around it, and mornings on the beach are peaceful. Being next door to Casa Marina means a larger resort ecosystem to draw on, with more dining choices and a long stretch of shoreline for walks.

Choosing a room: oceanfront rooms with balconies are worth the premium for sunrise views and the sound of the water; garden-view rooms are calmer on price. Families should ask about suites or connecting rooms. If you are bringing a dog, check the pet policy and fees in advance. Parking on site carries a daily charge, and rideshares or bikes are the easiest way to get around Old Town. Book watersports and cabanas early on holiday weekends.

Who it suits: families who want a beach and pool without giving up walkability, couples who want a calm oceanfront base, and dog owners. Travelers focused on nightlife might prefer La Concha or the harbor hotels, and those seeking a big beach should take a day trip to Bahia Honda. Pair a stay with mornings on the sand, afternoons in Old Town at the Hemingway Home and the lighthouse, and sunsets at Mallory Square or on a sail from the seaport.