Best Romantic Things to Do in Key West
Why Key West works for a wedding weekend: Casa Marina's 1920s beachfront grounds, The Reach Resort's only natural sand beach, and Old Town walkable from every real partner property.
Key West sits at the very end of US-1, the southernmost city in the continental United States, roughly a hundred-mile drive south of Key Largo. It is a different kind of wedding backdrop than the Upper Keys: Old Town's historic streets, Duval Street's nightlife, and the nightly sunset gathering at Mallory Square give it a livelier, more urban energy than the quiet bay-and-reef pace of Key Largo or the resort-and-golf scene of Islamorada.
Casa Marina Key West is the real choice for a ceremony that wants scale and history rather than an intimate pier setting -- a grand beachfront resort built in 1920, with sweeping lawns and the largest private beach in Key West. It is the property built for a wedding that wants room to spread out and a setting with a hundred years of its own story already behind it.
The Reach Resort has the more intimate version of the same beachfront setting: it sits on the only natural sand beach in Key West, a Curio Collection property with an intimate pool terrace, better suited to a smaller ceremony than Casa Marina's sweeping lawns. And The Marker Key West, in the heart of Old Town with three saltwater pools and an adults-only atmosphere, is the pick for a rehearsal dinner or bachelorette weekend that wants to walk to Duval Street rather than drive to it.
All three of these real properties sit inside Key West's compact Old Town core, which is the practical upside of a Key West wedding weekend: once guests arrive at the end of the Overseas Highway, the ceremony, the reception, Duval Street, and Mallory Square's sunset crowd are all a walk apart, not a string of rental-car errands.
Stays we have notes on near Key West, Florida Keys
Guide last updated Aug 25, 2026.
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