3770 Ala’oli Wy., Lihue
Perched on a cliff with panoramic ocean views, Timbers Kauai is serene and cozy, perfect for families and long stays. The forty-seven vacation rentals are multibedroom residences with the comfiest beds and sofas, beautiful high-end kitchens, spacious lanais, iPad concierge service, and luxury amenities that make everything just so easy. The property is stretched across 450 oceanfront acres, and the two infinity pools really will trick you into thinking they’re spilling into the Pacific. We highly recommend a tour of the property’s organic farm, from which the restaurant, Hualani’s, sources ingredients like sugarcane, bananas, and papayas. And the spa does a transformative Hawaiian lomi lomi massage—don’t skip the heated coconut oil scalp massage at the end.
2829 Ala Kalanikaumaka, Poipu
Kauai is paradise, in part because it's the least touristed of Hawaii's islands, but with that comes a dearth of good place to stay. One relatively new and excellent antidote to the housing crunch—particularly for families, or anyone traveling with other couples—is the Lodge at Kukui'ula, a private club in Poipu that stretches across 1,000 acres. Comprised of multi-bedroom homes—most with adjacent guest houses—it is really well done, with plenty of high-end touches and amenities. It is so well done in fact, that you might find yourself spending too much time sprawled out on the couch, and not enough time at the beach. While all the homes are equipped with lavish kitchens, the club restaurant is excellent, and serviced by an on-site organic garden. There's a multi-level pool, complete with hot tubs, a water slide, and a beach (the real beach is just across the road), a keiki play room lined with toys, DVDs, and all the things you might not have packed, including bouncy chairs and strollers, and an on-site outfitters staffed by locals who know all the island's secrets—what's better is that they'll take you there, or…
6867 Koolau Rd., Kilauea
Nestled on a secluded 5-acre estate in the Moloa’a hills on Kauai’s north shore, The Palmwood is a veritable sanctuary—as a bed-and-breakfast, it’s got a personal touch you aren’t likely to find at the major resorts. Inspired by the country inns found in the mountains of Japan, the rooms here are on the cozy side with warm, Eastern-inspired furnishings, and the grounds are lush and green. Best of all: this intimate, peaceful hideaway is close to some of the island’s finest attractions. As it is a real-deal B&B, we also hear that Auntie Eddi makes the very, very best breakfast. (Tip: you can reserve any one of their three rooms on Airbnb.)
St. Regis Princeville
5520 Ka Haku Rd., Princeville
Tucked away in a secluded beach cove a few miles from Hanalei, the St. Regis at Princeville is Kauai’s preeminent luxury resort. Boasting everything from pools and a spa to a kid’s club, this is a popular destination for those with a generous budget—but it’s still got the quiet, relaxed atmosphere you’d want for your Hawaiian getaway. The rooms here offer jaw-droppingly gorgeous, unobstructed ocean or mountain views, and their restaurant’s curated menu focuses on local delicacies, meaning you can enjoy an extravagant yet quintessentially Hawaiian experience in their staff’s very capable hands.
Waimea Plantation Cottages
9400 Kaumualii Hwy., Waimea
So there's nothing particularly splashy about Waimea Plantation, but that's precisely the point. The beach isn't particularly spectacular either, but that's no bother, either. These sprawling cottages, which occupy the grounds of a former sugar plantation, are ramshackle and adorable, and exactly what belongs at the beach. They're also perfect for a family, as they come equipped with kitchens and all that jazz—all the better for enjoying the fresh tuna sashimi from the nearby Japanese grocery store, Ishihara (seriously, it's insane). There's incredible surf to swim in to the west of the cottages in the naval base, and it's close to the bigger resorts on Poipu. The North Side and Princeville are a bit of a drive, but it's worth your while to hike along the Western side of Kauai: it's one of the more spectacular views in the world.