Docked in Paradise

Two side-by-side six-bedroom villas in a gated Key West community, with a pool to cool off in and a fire pit to gather around once the sun drops. Wraparound balconies span the full width of each level, catching the island breeze, and the palm-lined approach sets the mood before you've even walked in. When you're ready to venture out, Mallory Square's nightly sunset ritual and the bars and boutiques of Duval Street are both close at hand – and a guest experience team can map out the rest.

Home truths:
* The two villas sit side by side within the gated community but are separate homes, each with its own entrance, pool, and dock slip. If your group wants to move freely between them, you'll be stepping outside to do so.
* Two of the bedrooms – one in each villa – feature twin bunk beds in an open layout with no door. These rooms work well for children but offer less privacy than the other bedrooms, so it's worth factoring that into how you allocate sleeping arrangements across the group.
* The dock slips have no power or pump-out service, so plan accordingly if you're bringing a boat that needs either.
* The driveway at each villa accommodates up to four vehicles and a boat trailer, so larger groups arriving in multiple cars should have enough space.