Spanning more than 1,500 miles of the Pacific Ocean, Hawaiʻi’s five major islands — Oʻahu, Maui, Kauaʻi, the Big Island, and Lānaʻi (now largely owned by billionaire tech founder Larry Ellison) — each have their own distinct personality. Maui is defined by its broad beaches and statement villas; Oʻahu pairs cosmopolitan energy with the calm of the North Shore; Kauaʻi unfolds in rain-fed cliffs, dense greenery, and bursts of tropical bloom; the Big Island feels elemental, moonlike almost, in its lava-sculpted landscapes rising toward Mauna Kea; while Lānaʻi, pared-back and private, is quiet and shaped by low-key luxury. To experience Hawaiʻi in a more intimate way, choose a luxury Airbnb — architecturally compelling homes with private pools, seamless indoor-outdoor living, and generous lanais.
Maui
Beachfront Oasis
Splurge on this modern four-bedroom, three-bath home, featuring a full chef’s kitchen with quartz countertops, a bold backsplash, and seamless indoor-outdoor seating. After a day on Maui’s sandy shores, unwind by the secluded pool, complete with lounge chairs and a waterslide.
To Book: Airbnb
Kauai
Stunning Villa
Located in Koloa — close to pristine beaches, hiking trails, and river kayaking — this four-bedroom, four-bath villa (with separate guest house) features contemporary coastal décor, an outdoor shower, and a private lanai. Gather for sunset dinners before sinking into the hot tub.
To Book: Airbnb
Hawaii: The Big Island
Polynesian Pod-Style Home
Pairing luxury living with island authenticity, this five-bedroom, six-bath home offers an open-concept layout and heated saltwater pool, anchored by breathtaking views of Mauna Kea.
To Book: Airbnb
Spacious Home in Waikoloa Beach Resort
This four-bedroom, three-and-a-half-bath home celebrates island beauty with soaring vaulted ceilings and an airy, open design that brings the outdoors in. Start the morning with yoga in the tranquil courtyard surrounded by koi ponds, lily pads, and lush greenery.
To Book: Airbnb
Oceanfront Condo
This top-floor condo in Kailua-Kona is flooded with natural light and effortless sophistication. Relax with panoramic views, cushy outdoor loungers, and easy beach access.
To Book: Airbnb
Serene Showstopper
This luxe showstopper, located near the Kohola Coast, is defined by its extravagant outdoor space. We are talking private pool and hot tub, swing chairs, a fire pit, and a wood-burning pizza oven.
To Book: Airbnb
Oahu
Local Beachfront Living
Beachfront along Hale‘iwa’s turquoise shoreline, this three-bedroom, three-bath home has guests living like a North Shore local. Sway in the hammock under twinkling string lights or unwind on sunloungers as waves lap against the sand. Enjoy too the complimentary kayaks, surfboards, and scuba gear.
To Book: Airbnb
Modern Honolulu Penthouse
Featuring marble countertops, bamboo paneling, and gold detailing, this stunning penthouse suite is just steps from Waikiki Beach in the heart of Honolulu. We love the clever coffee bar (that doubles as a workspace).
To Book: Airbnb
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