Buying Vacation Homes in Hawaii

Owning a home on a tropical island amid swaying palm trees, balmy breezes, and ocean views is a dream for many. Buyers of vacation homes in Hawaiʻi are making that dream a reality, leading to immense 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.”

Moreover, demand for real estate throughout Hawaii is strong and significantly exceeds supply. An increasing number of individuals aspiring for vacation homes are purchasing them sight unseen, as per data from Vacasa. Buyers are increasingly relying on their agent’s assessments and online tools because properties are being sold rapidly.

Vacation homes in Hawaiʻi can be found in gated developments, single-family residential communities, multi-acre estates, resorts, and condominium projects. Each island—Oʻahu, Maui, Kauaʻi, Hawaiʻi, and Lanaʻi—offers unique vacation home options, although the availability, pricing, style, and amenities vary greatly. The islands also exhibit diverse microclimates, ranging from dry and desert-like to lush and green. Consequently, Donna Hansen of Hansen Ohana – Maui Luxury Real Estate has agents on each island, specializing in aspects such as rainfall, weather, and important considerations when purchasing property. Regarding luxury vacation homes in Hawaii, she stated, “Living in Hawaii is a luxury in itself.”

Kauaʻi – “The Garden Isle”

On the island’s south shore, Timbers Kauaʻi offers oceanfront residences, a championship golf course, farm-to-table dining available onsite, and luxury amenities. Chris Burden, chief development officer at Timbers, noted that “closings in 2021 doubled year over year.”

Also on the south shore, Kukuiʻula is spread over 1,000 acres, featuring golf, breathtaking ocean views, plantation-style architecture, and “barefoot luxury.” According to representatives from Kukui’ula, prices have surged by 30 percent or more in the past year. When potential home buyers cannot find their desired home, some have opted to build on available home sites. Kukui’ula is planning to introduce another new neighborhood to the market soon.

On the north shore of Kauaʻi, the Princeville area offers condos, townhouses, single-family residences, and home sites at a wide variety of price points.

Oahu – “The Gathering Place”

Some buyers of vacation homes in Hawaii seek the convenience of high-rise living, situated near shopping, dining, entertainment, and walkable areas. Honolulu offers many choices in sleek, modern buildings equipped with a plethora of amenities. The Ritz-Carlton Residences, Waikiki Beach features on-site pools, restaurants, and concierge services. At ONE Ala Moana, residents enjoy a heated pool, fitness center, yoga room, putting green, and more.

On the sunny leeward coast, Ko Olina hosts several vacation home communities within the oceanfront Ko Olina Resort. Options include condos, townhomes, and single-family homes, while the resort features four luxurious hotels, shops, golf courses, and a marina.

The north shore, famed for its powerful surf and serene beaches, is home to Turtle Bay Resort along with various condo developments such as Kuilima Estates and Ocean Villas at Turtle Bay. Presently, available inventory is minimal.

Hawaiʻi – “The Big Island”

Located on the warm, dry Kona-Kailua Coast, Hualālai Resort has been an acclaimed luxury destination since 1994, featuring a Four Seasons Resort, championship golf course, spa, stunning beaches, and a prime location. The current inventory is low, and turnover is minimal. According to Kildow of Hualālai Realty, “Many buyers are looking for a home that will accommodate friends and family, intending for the home to remain in the family for generations.”

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

In Hilo, situated on the island’s northeastern side, the climate is moist, yielding verdant vegetation, waterfalls, and lush gardens. A variety of homes, condos, and building sites are available at Hilo Country Club Estates.

Maui – “The Valley Isle”

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

On the west shore of Maui, Kaʻanapali is home to several prestigious golf courses, nestled between Lahaina and Kapalua. The historic whaling town of Lahaina features homes, condos, an array of restaurants, and a marina.

Spreckelsville, on the north shore, was once a sugar plantation founded by the Spreckels Sugar Company. The “Upcountry” area offers higher elevations and cooler temperatures, presenting residential neighborhoods, many of which boast excellent ocean views.

Lanaʻi – “The Pineapple Isle”

Once a hub for pineapple plantations, Lanaʻi features one town, Lanai City, along with the coveted Four Seasons Resort Lanaʻi and Sensei Lanai, a Four Seasons Resort. Unfortunately, very few vacation homes remain available.