Mallory & the Moon

Two villas, two private pools, and two docks sitting right on the water – this Key West home is built for a crowd that wants to do things properly. Enjoy an alfresco lunch above the waterway as palm trees catch the breeze, then spill out onto the pool terrace for the long afternoons that follow. Inside, the calm, design-led bathrooms and bright living spaces with waterway views keep things feeling considered, not chaotic, even for a large group. Mallory Square's famous nightly sunset celebration and the bars and galleries of Duval Street are both close by when you're ready to venture out.

Home truths:
* The accommodation here is set across two separate villas – one has six bedrooms and the other has eight. Each villa has its own private pool and dock.
* The docks have no power or pump-out service to the slips, and the Florida Keys are noted as notoriously difficult waters to navigate. If you're planning to arrive by boat or explore by sea, factor in local knowledge and check berthing requirements in advance.
* The driveway accommodates up to four vehicles and a boat trailer across both villas, so if your group is arriving in multiple large cars it's worth coordinating ahead.