From a private Hawaiian bungaloo called Shangri-La to a fully staffed Greek Isle villa—here are 10 island homes worth exploring.
Shangri-La, Big Island
On the Big Island, you feel that energy — a combination of sun, surf and seismic activity — from the moment you get off the plane till the moment you leave, swearing you’ll come back to stay and soon. And living here brings the energy home, even if it’s only for a few weeks this time. Nestled among the coconut trees, Shangri-La captures that almost indescribable, easygoing Big Island feel. The villa’s several structures sit right on a thermally heated natural lagoon filled with native tropical fish — and you snorkeling among them. Beyond the rock walls, sea turtles swim in the open Pacific Ocean. The funky town of Pahoa lies a few miles west for -resupply runs and to share life with the locals — until you become one. Sleeps 6; rates from $375. bigislandvacationrentals.com
Il Gabbiano, Sicily
Certain cultures lend themselves perfectly to villa living, namely those where daily life — invigorating walks, healthful meals, deep rest — takes on import greater than the sum of its parts. Such a place is the Italian island of Sicily, equal parts long tradition and living for today. Rambling to the market for olives and fresh goat cheese, sniffing the steam from baking bread, drinking Marsala wine bottled down the road as you look over the water, it all adds up to an experience that feels less like a vacation and more like a life well spent. Set that in the villa called Il Gabbiano, built into the cliffs with private stairways down to the Tyrrhenian Sea, and the island life becomes a celebration. Sleeps 5; rates from $2,600. thinksicily.com
Samudra, Thailand
The villa of Samudra, “meeting of the waters,” sits on a rocky point on the southern tip of the Thai island of Ko Samui. The villa’s 12 structures — all for you — comprise an eclectic atlas of well-considered design: doorways, windows, chairs and tables from China, India and Thailand; a temple carried whole from Bali; rich textiles and artworks; and pools and pathways lined with quarried stone. And the effort to harmonize doesn’t cease with the physical here. With your bare feet on the mandala-shaped golden teak floor of the Octagon yoga studio and your eyes sweeping the ocean, you’ll feel lifted to a higher plane. Want even more harmony? Stroll to Kamalaya wellness sanctuary down the beach. Want a break from harmony? A short ride takes you into the almost-anything-goes nightlife of Ko Samui. If you’re going to rent the island life, get the whole faraway, exotic thing and a sense of community. Stay a month! In the words of one guest and lifelong islands reader: “Samudra embodies Thailand — smiling faces, wonderful food, spiritual sunsets. This is it.” Sleeps 10; rates from $800. samudra-samui.com
Villa Skinos, Ithaca, Greece
“Keep Ithaca always in your mind. Arriving there is what you are destined for.” So wrote the Greek poet Constantine Cavafy in 1911. He went on to say you should go in old age when you’re rich with experience. Fair enough. Or you could go now — mid-odyssey — and bring your whole crew! Very Greek and truly welcoming, Villa Skinos feels like a home you’re returning to. It sits on its own bay and features a captained yacht and speedboats for exploring the sparkling and myth-rich Ionian Sea. Dive in. A full staff prepares authentic Greek meals and makes you feel like family, while you take jaunts to the village taverna and enjoy what some call the most beautiful of the Greek islands. Sleeps 14; rates on application. www.fivestargreece.com
Sandy Beach House, Kauai
Life on Kauai is slow, lush and easy — for and by the water. That’s better experienced in a house than a hotel room, and this may be the best. Sitting on its own slice of beach, Sandy Beach House offers water sports and ocean swimming right outside — with mellower Lawai Beach blocks away, plus surfing at Prince Kuhio Beach and family-friendly Poipu Beach within short drives. The National Tropical Botanical Garden sits across the street, preserving Kauai’s amazing flora along with endangered -tropical-plant species from around the world. Nearby in the other direction there’s the famous Spouting Horn where the waves meet the lava shore. For longer-term provisioning, Lihue is 30 minutes away. Location isn’t everything — the house’s sunset-facing bedrooms, kitchen and decks are pretty cool too — but if it were, this one would be hard to beat. Sleeps 6; rates from $1,050. parrishkauai.com
Shogun, Mustique
Proportion, position, precision. These attributes of refined design cannot be rushed or quibbled over. Shogun Villa stands as testament — voiced through its choice of woods and placement of walls and windows — that perfection is worth the time and expense. Built into a five-acre Japanese-style garden on a bluff 300 feet above the Caribbean, the compound feels almost painted in, foliage along the path and koi in the pond like brush strokes, the light suspended. The main house commands views of Britannia Bay from its salon and sun decks. Little Shogun, a two-bedroom cottage separated from the other buildings, adds yet another layer of privacy. Traveller’s Tree Cottages, ideal for kids or your personal staff, perches above the complex. And speaking of layers, the whole place — stone flagstones, fine linens, rooftops, sea below and sky above — enfolds your moments here. It may be an extended vacation, but it feels like reverence. Go ahead, try not to wonder what your time at Shogun means. Here’s a hint: It means you did something right. Sleeps 18; rates from $30,000. www.shogunmustique.com
Villa North Island, Seychelles
For a couple seeking privacy — but with pampering — this place could top the list. The outlying islands of the Seychelles are less about cultural immersion and more about azure immersion. Tucked in Takamaka Forest away from the other 10 villas on private North Island, this signature spot offers pure seclusion. To get more privacy than this, you’d have to sail solo around the world, and then who would bring you cocktails? Hand-built by local craftsmen of wood and local stone, the house has wraparound views out to Anse d’est (east beach). That’s it for entertainment. Share it with someone you really like. Sleeps 2; rates from $3,700. www.north-island.com
Clytha Castle, Wales
Once upon a time, in a castle in the heart of Wales, a fairy tale waited only for its heroes. That’s where you come in. Built in 1790, the castle was renovated in 1974 to bring 18th-century romance into the modern age. Or almost — there’s still no TV. And the kitchen in the south tower has no microwave, but from its windows, you may see deer frolicking in the forest — a fair trade. Run by the Landmark Trust, which maintains historic properties all over the British Isles, the castle fits snugly into the Welsh countryside. If a knight in armor happened by, you wouldn’t be surprised. The local pub lies within walking distance, the town of Abergavenny a short drive away and cosmopolitan Cardiff not much farther. Or you could lay in a leg of lamb and a jug of mead to let your fairy tale continue. Sleeps 6; rates from $188. landmarktrust.org.uk
The Istana, Bali
Villas all over the world promise Bali-inspired architecture, furniture, pavilions and landscapes. On Bali, they just call that “home.” This elegant villa on the island’s southern tip has westward views over white-sand beach and colorful reef, plus some of the best surf and sunsets on earth. Turn around to see the main pool, infinity-edged and lined with green granite, plus groomed lawns, five suites (the master suite with its own pool), spa, theater, extra rooms and fun for kids, plus dining and entertaining spaces for grown-ups. A staff of 30 pampers you. The key feature, of course, is the island itself. Istana, like all the best villas, lets you join the scene and also retreat. Engage, indulge, repeat. Uluwatu Beach is a short walk, Uluwatu temple a short ride in the chauffeur-driven minivans. Sleeps 10; rates from $1,750. theistana.com
Alata Channel House, Turks and Caicos
If you’re hiring a house in the Turks and Caicos, you probably want relaxation, views of blue water and a rollicking rum party you can reach quickly but can’t hear from the veranda. Built of Jamaican hardwoods on an all-but-private stretch of white-sand beach, this house admits the breeze and ocean sounds but prohibits worries. And the urban hub of Providenciales is a short drive or sail if you get bored. This is pirate luxury, plush and hidden from view but not too far from the action. Sleeps 8; rates from $700. globalartichoke.com
