With Saint Martin’s mountainous landscape rising up from the Caribbean Sea only four and a half miles to the south, Anguilla makes for a noticeable contrast with its arid, scrub-covered terrain. However, for what it lacks in vegetative beauty, the island compensates with pristine, sandy beaches and a distinctive Caribbean culture. The island’s four luxury resorts—Malliouhana, Cap Juluca, CuisinArt, and the Viceroy—all line the western end of the island, but travelers seeking a quieter retreat make the trek to the island’s northern shore, where Àni Villas (www.anivillas.com), a pair of five-bedroom villas, offer 25,000 square feet of private living space.

The villas can be booked individually ($30,000 to $50,000 per week) or together ($51,000 to $85,000 per week), and boast infinity swimming pools, hot tubs perched along a cliff overlooking the island’s best spot for snorkeling, a fitness center, and a synthetic grass tennis court. But it is the property’s commitment to providing a customized itinerary with access to some of the island’s unique attractions that separates it from other Anguilla properties. "The island is really owned and governed by Anguillans, [and that’s] created this very relaxed vibe for tourists where people are genuinely welcoming and warm and appreciative on the island," says Ira Bloom, the head of development for Àni Villas. "At the same time, you get an authentic Caribbean feel because there is a local population."

For guests seeking interactions with those native Anguillans, general manager Bonnie Bloom can arrange trips to Sandy Ground, with its stretch of thatch-roofed beach bars, or to Planet Dune, a tree house–like nightclub owned by Bankie Banx, the island’s famous reggae singer, who often—but not predictably—plays sets of his island-inspired music as well as covers of classic American folk songs. The villas’ staff also can provide guided mountain bike treks along the dramatic and uninhabited shores of the island’s east end, and complimentary greens fees for four each day at the Temenos Golf Club, a 7,000-yard Greg Norman–designed course punctuated by white, Mediterranean-style villas and vistas of the Caribbean Sea and Saint Martin. And while in-house meals at the villas are included every day, Bonnie says that they also encourage dining at some of the island’s most reputable restaurants. "When we get the booking, we start doing the itinerary with the guest as soon as possible," she says. "We book them at various restaurants, especially during the high season because it’s not guaranteed that you can get a reservation there."

Horseback rides along the beach, diving and snorkeling excursions, and boat trips to Sandy Island, a small spit of land that has a restaurant known for its beach barbecues of local lobsters and crayfish, all can be arranged. While similar services are available at the island’s other luxury resorts, it is the sense of privacy that sets Àni Villas apart. "We strive to get people as much of a full Anguilla experience as we can," says Ira. "We want people to fall in love with Àni Villas in Anguilla, but we want people to fall in love with Anguilla, too. With our knowledge and experience, we want people to get the most of the island while they’re here."