Best Islands To Live On: Hawaii Top Houses

For our Best Islands to Live On ranking, we've highlighted editors' picks of the best houses for sale or for rent in Hawaii, from beachfront homes to hilltop estates.

See how to move or retire to Hawaii in our new Best Islands to Live On: Hawaii Guide and read more in our Ultimate Best Islands to Live On Guide.

Big Island Hawaii Home for Sale Realtor
**West Shore, Big Island
$28,000,000 ** While the Big Island is usually No. 1 — or close to it — on the Best Islands to Live On annual ranking, this $28 million 6,600-square-foot home on the west side of the Big Island is not the No. 1 most expensive house listed in the Hawaiian Islands. In fact, it's only No. 3. Still, if you can settle for five beds, six baths and views from your pool that will make you weep with joy, this house is worth it. See the real-estate listing on |
Oahu Luxury Villa for Rent on North Shore
North Shore, Oahu
$4,800 a night
If you aren't ready to move to Hawaii quite yet, we really like the selection of rental homes available on Picture staying at this five-bedroom luxury villa on the North Shore of Oahu. If you're not ready for down payment, you can get this villa for $4,800 a night and up to see what living on Oahu would be like, away from all the Honolulu tourists. You may never leave. See the rental listing on |
Big Island Hawaii Sothebys resort home for sale
West Shore, Big Island
For a true permanent vacation, relax at this six-bedroom, 9,000-square-foot home on the Big Island. While this mansion itself feels like a resort, with its koi ponds, sauna, workout room, tennis court and staff quarters, it includes access to the Mauna Lani Resort for lounging at the secluded beaches and golfing on the championship courses. What more could you want from life in Hawaii? See the real-estate listing from Sotheby's International Realty. |
Kauai North Shore Hawaii home for sale
North Shore, Kauai
This view accounts for about $23,000,000 of the asking price; that perfect little cottage is the other $1 million. Actually, location really is everything in Hawaii. It just so happens that Kauai is the location that most ISLANDS editors want to be at any given time. We're pooling our money now to buy the nearly 30 oceanfront acres with views of Secret Beach and the Kilauea Lighthouse, then build a few more cottages for the ISLANDS editors. Unless you beat us to it. See the real-estate listing from Sotheby's International Realty. |
Kauai Hanalei home for sale
Hanalei, Kauai
So let's say you want to live on Kauai but need a home a bit more modest than a mansion on top of a bluff. Just a short walk from Hanalei Bay is this three-bedroom, 2,3000-square-foot home, beautiful on the outside and in. An open layout with lots of windows gives you a waterfront view in one of the prettiest corners of Kauai. See the real-estate listing on |
Kauai Hawaii Kalihiwai house for sale
Kalihiwai, Kauai
The numbers of this house only tell part of the story: 5 bedrooms, 6,200 square feet, five acres. Few homes are as architecturally inspiring as this one above Kalihiwai Bay on the north shore of Kauai. The hand-cut stone lanais, the wide-open views, the pool and infinity-edge waterfall all seem hewn from this 180-foot hilltop overlooking the bay and the Pacific beyond. See the real-estate listing on |
Oahu Hawaii Presidential Estate home for rent
Kailua, Oahu
$3,571 per night
Usually when we see "5-Star Presidential Estate" or a claim that "the President slept here," we're skeptical. But this stunning five-bedroom gated beachfront home in Kauai really is the place where President Obama has spent three recent winter vacations. No matter your politics, that's a pretty good endorsement. You can stay at the "Winter White House" too and try living not just the island life, but the presidential life too. See the rental listing on |
Kapalua Maui Hawaii luxury home for rent
Kapalua, Maui
$2,995 a night
As beautiful as this home is, that starting price for a nightly rental can seem pricey. But the listing is smart to show how this 6,100-square-foot home and accompanying 1,000-square-foot guest house can accommodate up to 14 people. That becomes potentially a better deal than the nearby Ritz-Carlton (which we've stayed at and loved). A retired couple lives here when it's not rented out, so you could try not just the Hawaii life, but what it would be like to retire in Hawaii. See the rental listing on |
Haiku Maui Hawaii house for sale
Haiku, Maui
Relative to some of the hilltop oceanfront real-estate listings in Hawaii, this perfect Hawaiian estate on Maui could actually be a bargain at less than $12 million. You don't just get that perfect 10-bedroom, 9,600-square-foot historic home, you get a guest cottage, three caretakers' cottages, a tennis court and swimming pool. And a couple ISLANDS editors are big-time windsurfers, so they dream of snapping up this estate so they'd be close to famous Hookipa Beach Park. See the real-estate listing from Sotheby's International Realty. |
Kapalua Maui Hawaii luxury home for sale
Kapalua, Maui
If you really, really want your own corner of Maui to live on, this is the house for you. Built in 2012 within the Kapalua Resort and has 120-feet of beachfront. The six-bedroom, 7,800-square-foot house is behind one gate, but two in an ultra exclusive neighborhood that only has four houses. See the real-estate listing on |
Kilauea Kauai Hawaii home for sale
Kilauea, Kauai
Imagine living in a luxury Bali resort. On Kauai. That's a dream we didn't think was possible until we saw this listing for a 4,400-square-foot home designed by an architect known for his Balinese style in crafting resorts and spas. With an impressive pool, spa and cascading lily ponds, the house is built of hardwood with Indonesian lava stone in the exterior living spaces. Plus, there's a bedroom in an Asian Rice Barn. We're struggling to find words stronger than "dream come true." See the real-estate listing on |
Oahu Luxury Rental home in Hawaii
Laie, Oahu
$1,100 per night
After browsing some of the previous million-dollar-plus magnificent homes for sale in Hawaii, the starting price of $1,100 a night for this beachfront house rental seems cheap. It is an amazing deal: four bedrooms all with beachview lanais and 100 feet of beachfront. It's an ideal way to rent the island life. See the rental listing on |
Big Island Hawaii most expensive house for sale
Kailua-Kona, Big Island
Yes, this is the most expensive home for sale in the Hawaiian Islands. Why? It's a 9,400-square-foot, six-bedroom, eight-bathroom masterpiece on the Big Island, with a modern design (built in 2007) that opens up the outdoor living space to let you feel like you're one with Hawaii. If you buy this home, please let ISLANDS know — so we can come visit you as you live the greatest island life. See the real-estate listing on |