Where to Buy a Vacation Home in Hawaii: An Island-by-island Guide

Welcome to your tropical home away from home.

Owning a home on a tropical island amid swaying palm trees, balmy breezes, and ocean views is a dream for many of us. Buyers of vacation homes in Hawaiʻi are making that dream come true, creating huge demand for island properties. According to Rob Kildow, director of residential sales at Hualālai Realty on the Big Island, "The pandemic caused many people to hit 'pause' and take stock of what was important to them, from careers to remote work and spending time with family. People have been looking for safe harbor and are still actively seeking their Hawaiian dream home."

Turtle Bay, Resort, North Shore, Oahu, Hawaii
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Demand for real estate throughout Hawaii is strong and outweighs supply significantly. An increasing number of people desiring vacation homes are even purchasing them sight unseen, according to data from Vacasa. Buyers are relying on their agent's assessment of the home along with online tools because properties are selling so quickly.

Vacation homes in Hawaiʻi are located in gated developments, single-home residential communities, multi-acre estates, resorts, and condominium projects. The islands of Oʻahu, Maui, Kauaʻi, Hawaiʻi, and Lanaʻi all offer vacation homes, although availability, price, style, and amenities differ widely. Within each island, microclimates range from dry and desert-like to lush and green. For that reason, Donna Hansen of Hansen Ohana - Maui Luxury Real Estate has agents on the other islands who specialize in details like rainfall, weather, and things to watch for when purchasing property. Asked about luxury vacation homes in Hawaii, she responded, "Living in Hawaii is a luxury in itself."

We couldn't agree more — and with that in mind, here's a look at where to buy vacation homes in Hawaii.

Sun setting over Kukuiula Bay, Kauai, Hawaii with clouds reflecting in the pool of water in the lava rocks
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Kauaʻi - "The Garden Isle"

On the island's south shore, Timbers Kauaʻi features oceanfront residences, a championship golf course, farm-to-table dining (with an on-site farm), and luxury amenities. Chris Burden, chief development officer at Timbers, told T+L that "closings in 2021 doubled year over year."

Also on the south shore, Kukuiʻula is set on 1,000 acres with golf, ocean views, plantation style architecture, and "barefoot luxury." According to reps for Kukui'ula, prices have accelerated 30 percent or more in the past year. When prospective home buyers can't find the house they want, some have built on available home sites. Kukui'ula is planning to bring another new neighborhood to market in the near future.

On the north shore of Kauaʻi, the Princeville area features condos, townhouses, single-family residences, and home sites at a wide range of prices.

Oahu - "The Gathering Place"

Some buyers of vacation homes in Hawaii are looking for the convenience of high-rise living, close to shopping, restaurants, entertainment, and walkable destinations. Honolulu offers many options in sleek, modern buildings with a variety of amenities. The Ritz-Carlton Residences, Waikiki Beach features on-site pools, restaurants, and concierge services. At ONE Ala Moana, amenities include a heated pool, fitness center, yoga room, putting green, and more.

On the sunny leeward coast, Ko Olina features a variety of vacation home communities on the grounds of the oceanfront Ko Olina Resort. Condos, townhomes, and single-family homes are available, and the resort includes four luxury hotels, shops, golf courses, and a marina.

The north shore, known for powerful surf and quiet beaches is home to Turtle Bay Resort along with several developments of condos in Kuilima Estates and Ocean Villas at Turtle Bay. Available inventory is minimal at this time.

Hawaiʻi - "The Big Island"

Set on the warm, dry Kona-Kailua Coast, Hualālai Resort has been an acclaimed luxury destination since 1994, with a Four Seasons Resort, championship golf course, spa, stunning beaches, and ideal location. Currently, inventory is low and turnover is minimal. According to Kildow of Hualālai Realty, "Many buyers are seeking a home that will accommodate friends and family with the intent [that] the home will stay in the family for generations to come."

One Ocean, on the southern edge of Mauna Lani, Auberge Resorts Collection on the Kohala Coast, is an oceanfront gated enclave among lavascapes and golf fairways. A limited number of luxury contemporary homes are available, with access to select experiences at the resort.

In Hilo, on the northeastern side of the island, the climate is moist, and vegetation is green, with waterfalls, fertile rainforests, and lush gardens. A variety of homes, condos, and building sites can be found at Hilo Country Club Estates.

Beautiful landscape of South Maui. The backside of Haleakala Crater on the island of Maui, Hawaii
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Maui - "The Valley Isle"

In South Maui, Makena features some of the most luxurious vacation homes in Hawaii, with golf, tennis, boating, and secluded beaches. In the same area, Wailea, Maui Meadows, and Kihei offer condos, home sites, and residences.

On the west shore of Maui, Kaʻanapali, home to several famous golf courses, is located between Lahaina and Kapalua. The historic whaling town of Lahaina includes homes, condos, restaurants, and a marina.

Spreckelsville, on the north shore, was once a sugar plantation founded by the Spreckels Sugar Company. "Upcountry," away from the coasts, with higher elevations and cooler temperatures, offers residential areas, many with excellent ocean views.

Lanaʻi - "The Pineapple Isle"

Formerly home to pineapple plantations, Lanaʻi has one town, Lanai City, and is home to the coveted Four Seasons Resort Lanaʻi and Sensei Lanai, a Four Seasons Resort. Very few vacation homes are available.

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