It’s a tale of two sisters—both entrepreneurs and Caribbean girls. Cayman Islands natives with worldly backgrounds and an innate sense for hospitality, Heather Lockington and her sister turned a chunk of beachfront land on Grand Cayman into a lovely and serene luxury villa getaway. It’s sophisticated enough to satisfy the jaded “Please-I’ve-seen-everything-in-the-Caymans” crowd and comfortable enough to make guests feel right at home—whether they’re a honeymooning couple or a family with small children. 
With only four plantation-style cottages tucked along a private beach, surrounded by palms and a tall encircling hedge, Cotton Tree is very much a specialty lodging experience, but you never feel alone or cut off from the world. Need milk for your morning coffee? If it’s not in the refrigerator, the morning staff will happily bring it to your door. Want to do an intimate dinner party in your cottage with cocktails poolside? Cotton Tree engages an in-house chef and an on-call chef for special occasions, plus Harvey Setterfield, the best sommelier on the island.
Cozied up on a picturesque little beach, blissfully private and Caribbean chic, this tiny cottage hotel definitely evinces a woman's touch in the decor. Few men would ever complain about that; it just means that the details are taken care of, with an eye for beauty—the fairy lights strung through the trees that glow softly when guests are out at night. The cabanas for two, so perfect for a mid-day nap by the pool. Not to mention the fact that there are more chaise lounges and cabanas than the maximum occupancy would ever require.
No guest will ever go without a comfy spot in the sun here, a bottle of Caribbean rum waiting in the refrigerator, or fresh flowers in the foyer. And no guest should go without the soothing experience of a massage by the sea in the open-air spa pavilion.
The special quality of Cotton Tree is that it manages to provide an authentic taste of the high-end Caymanian expat lifestyle, even if you only stay the minimum three nights. The cottages—pastel on the outside, contemporary island-chic on the inside—are exactly what world-weary travelers want when they're at rest. The property layout takes no thought to navigate: Step outside your cottage and walk 10 paces to the beach or 20 to the pool. For people who tend to get lost in the endless hallways and foyers of a big hotel, this is a de-stresser in itself.
Another charming feature is the locale. Not boxed into some concrete development on the side of a highway, as most of Grand Cayman's hotels and condos are, but instead a pretty, upscale residential street just outside of town. When the gate rolls open and the sisters come out to greet you, you know they've been expecting you.
And in the evening, if you're lucky enough to be there for a fish fry or a poolside cocktail party (Heather throws such gatherings regularly), you'll meet the artists currently exhibiting in the best island galleries, the sommelier who stocks all of Grand Cayman's best cellars, the local restaurant critic who can tell you where to find the freshest fish in town...and you will know that you've stumbled into the inner circle of authentic, friendly, Caymans luxe life.