Cheeca Lodge’s claim to vacation fame has always been the Florida Keys trifecta: fun, fishing, and family. But now the Islamorada resort, a Keys landmark since 1946, is appealing to a new breed of traveler with a gated enclave of 11 villas with butler service and a private beachfront.
The charming clapboard cottages that make up the Casitas at Cheeca Lodge were acquired from neighboring The Moorings and rebranded as Cheeca’s premium product. This luxurious mini-community offers all the amenities of the greater resort with the important addition of privacy, space to roam, and a sense of serenity you won’t get at the bustling 27-acre property. It feels, in a word, like a hideaway.
The one- or two-bedroom villas are designed in the Keys vernacular, with colorful shutters, covered porches, and balconies off the upstairs bedrooms. Three sit directly on the private beachfront, with the rest tucked inside mature landscaping a few steps from the beach, where private chaises, hammocks, and watersports await. Butler service extends to the Casitas beach and pool, so all you need to do is send a text and cocktails and lunch magically appear.
To experience the full gamut of amenities, you will have to exit the Casitas gate and venture into the main resort, but the tiki bars alone are worth it. (What is a Keys weekend, after all, without a proper margarita?) The 525-foot pier is also a must, if only to sample the legendary fishing that has attracted presidents and aristocrats to Cheeca since the 1950s. Grab a rod and some bait from the activities hut (it’s complimentary) and try your luck in the teeming waters.
As golden hour sets in, cross the street to Pierre’s and Morada Bay Beach Café, two local favorites that were also included in the acquisition. Pierre’s is the swankier of the two, but there’s nothing like the toes-in-the-sand vibe of the Beach Café, which has an unforgettable view of the sunset (and pretty impressive lobster sliders). Or stay in, order from one of Cheeca’s three on-property restaurants, and enjoy dinner on the porch to the soundtrack of lapping waves. In the immortal words of Jimmy Buffett, “When you lose yourself, you find the key to paradise.”