South Kohala
This 4200-sq ft, four-bedroom villa is as luxurious as rentals get in Kohala. Designed by an architect, the space expertly utilizes natural light and…
South Kohala
This 4200-sq ft, four-bedroom villa is as luxurious as rentals get in Kohala. Designed by an architect, the space expertly utilizes natural light and…
Moloka'i
The layout and furnishings are tidy and functional at these two vacation cottages just east of mile marker 18. Each cottage sleeps four and comes with…
Princeville
Set on a loop road in the heart of Princeville, this manicured complex of individually owned condos is not cliffside, nor does it have sea views, but it…
Waikiki
This hip boutique hotel is a lovely sanctuary near Kaimana Beach. At the calm southern edge of Waikiki, many rooms have panoramic views of Diamond Head…
Kihei
Wooden cottages, cozy hammocks, picnic tables, swaying palms – this place looks like the tropical version of summer camp. Sporting recently refreshed…
Princeville
Perched atop the cliffs, just short of the Princeville Resort, Pali Ke Kua offers an easy trail down to its namesake beach, also known as Hideaways. Some…
Windward Coast
The grassy, botanical-garden-surrounded tent sites at the base of the Koʻolau Range are cool and green, fed by frequent mists. With an overnight guard and…
Lihuʻe
Set beside its own thin ribbon of sand (no swimming), this sprawling resort sports 350 boutique-on-a-budget rooms, four pools complete with waterfalls,…
Princeville
Perched cliffside with nothing but water between you and Alaska, this 1200-sq-ft, two-bedroom, two-bath unit in the Ali‘i Kai development, complete with…
Hanalei Bay & the North Shore
At the only North Shore county campground to remain open at press time, you set up your tent on well-shaded lawns just back from the beach, with restrooms…
Hilo
Rent this 2000-sq-ft, one-bedroom guesthouse and make believe you live in Hilo. With inviting lounging areas and chef-worthy full kitchen, this place is a…
Princeville
This large condo development, perched on the grassy Princeville cliffs, is comprised of three-story wooden turquoise-brushed buildings with slanted roofs…
Princeville
Basking in 180-degree views of the deep blue Pacific from their gorgeous cliffside location, these wind-weathered, wooden-shingled condos make a dramatic…
Poʻipu
This romantic boutique resort occupies a unique niche in Poʻipu. A decidedly adult property, it's a bold exploration of design instead of the Hawaiiana…
Hilo
Just across the Singing Bridge near downtown Hilo, find three immaculate guest rooms within sight and sound of the bay. Rooms are tastefully tropical…
Waimea Canyon & the Westside
Glorious rural accommodation in the large guestroom of a private home, kitchenette-equipped and facing across a huge meadow with fruit trees. Breakfast is…
Hamakua Coast
Surrounded by wildly thriving flora, this aptly named hideaway has sweeping horizon views and a laid-back feel. More lived-in than brand new, it's the…
Hilo
Four breezy rooms below the main house enjoy sweeping ocean views and refreshing trade winds. The lanai is shared, but partitioned, with outdoor seating…
Kona Coast
Amid tropical gardens, this plush, romantic four-room B&B is filled with rich fabrics, carved bed frames and Asian and Hawaiian decor. Guests share a hot…
Hamakua Coast
Set in an unpretentiously elegant home, this B&B strikes a nice balance between professionalism and warmth. The eight ocean-view rooms are spacious, with…
Kiahuna Plantation Resort Kaua‘i by Outrigger
Poʻipu
This wonderfully underappreciated resort harks back to the golden age of Kaua‘i tourism. Surrounding massive central lawns with the feel of an oceanfront…
Poʻipu
The Sheraton enjoys an undeniable advantage, occupying a prime stretch of sandy, swimmable, sunset-perfect beach, with a pool and luau gardens right by…
Poʻipu
If you're traveling with a larger family, this oceanfront luxury house rental, might just be heaven. The place sleeps eight and spreads over 1800 sq feet…
South Kona Coast
You're guaranteed to swoon at the heady ocean views from the shared lanai, guest living room and some bedrooms at this the property on a 5-acre fruit farm…
Hanalei Bay & the North Shore
This chic and comfortable house has an enviable location only a short walk from the beach. Expect modest luxury, Hawaii-style, with a polished wood…
Waimea Canyon & the Westside
Make advance reservations online to camp at the primitive sites in Polihale State Park. You’ll be rewarded with beautiful sunsets, late afternoons and…
Poʻipu
This luxurious cottage is just a stone's throw from Baby Beach. Everything feels updated and clean. The little slat-board bungalow just catches ocean…
Poʻipu
Set on a grassy outcrop that juts into the sea opposite Prince Kuhio Park, this aging but perennially popular three-story oceanfront complex claims the…
Poʻipu & the South Shore
After a long day’s adventures, relax at this class-act B&B with a 50ft saltwater lap pool and great views over Lawa‘i Valley. The three rooms are…
South Kohala
This two-bedroom house is decked out with hardwood floors, bright artwork and decor that evokes a seaside aesthetic, which makes sense, seeing how close…
South Kohala
Stay overnight in one of six cabins near Hapuna Beach, an awesome location for sunset watching. While rather makeshift, the location is essentially…
Waimea Canyon & the Westside
This two-story home looks right onto the water – it really is the bee's knees for a family getaway. Everything has been updated; expect vaulted ceilings,…
Waimea Canyon & the Westside
Sleeping up to six people, this luxurious oceanfront two-story home has terrific views from nearly every room. Teak furniture, classic styling and an…
Poʻipu
For the ultimate splurge, try this private South Shore pleasure palace that blends Asian motifs with Hawaiian colors. The 2000-sq-ft house only has 1…
Four Seasons Resort Oahu at Ko Olina
Pearl Harbor & Leeward O‘ahu
The Four Seasons resort is right on the beach and is popular with those wanting to avoid the Waikiki scene, but still have all the trappings of top-end…
Hanalei Bay & the North Shore
A 500-sq-ft wooden cottage on a working, 7.6-acre organic farm. There's a vaulted ceiling in the living room, a queen bed in the bedroom, and a hot tub…
Waikiki
Terraced ocean-view rooms and suites are elementally chic, showing off teak doors and marble baths. Not all rooms have balconies and some also lack basics…
South Kona Coast
This whole home rental earns its name from its sloped, Asian-style roof, but that's hardly the highlight. Multiple home levels are decked out with…
Poʻipu
A little less sophisticated than the other Parrish Collection Cottages, this 3-bedroom home has terrific ocean views from every room and an oceanfront hot…
Waimea Canyon & the Westside
Rented in its entirety, this green-painted oceanfront house offers three suites with cherrywood and bamboo furnishings, and two with private lanai and…