Aloha, my fellow island dreamers!
I know how you feel – the thought of living on a beautiful, tropical Hawaiian Island seems like an absolute paradise. But with so many islands to choose from, it’s tough to know which one will be the perfect fit for your lifestyle, right? Fear not, because I’ve done all the legwork for you. Over the past couple of years, my boyfriend and I have been island-hopping across Hawaii in search of the best spots to call home.
You see, we were once undecided just like you. We understood that finding our dream island was about more than just pretty beaches and palm trees; we needed to consider things like climate, job opportunities, housing availability, and overall quality of life. So we became amateur experts at sifting through what each island had to offer – both good and bad!
Having immersed ourselves in this amazing journey together (literally!), I’m confident that our experiences can guide you toward your own personal slice of Hawaiian heaven. And hey – if nothing else – it’ll give us an excuse to relive some unforgettable moments!
Warning: With all this talk about idyllic paradises and heavenly hideaways, don’t blame me if your wanderlust kicks into high gear!
So grab a fruity umbrella drink and let’s dive into everything you need to know about finding your dream home in Hawaii already!
As the most famous island in Hawaii for tourists and holiday-goers, everyone has heard something or the other about Oahu. It’s home to the infamous Waikiki beach, the Diamond Head volcano, and some of the best surfing beaches in the world.
But if you’re looking to move here permanently, consider that it has the most expensive housing market in the U.S., and get to know some more general and interesting facts about Oahu first, which I’ve mentioned below:
Also Known As: The Gathering Place
Capital: Honolulu (also the capital of the State of Hawaii)
Area: 596.5 square miles (third largest in Hawaii)
Population: 1,016,508 (2020)
- The Kualoa Ranch in Oahu was the filming site of Hollywood blockbusters like Jurassic Park, Pearl Harbor, Jumanji, Magnum P.I., Pirates of the Caribbean, and many more.
- Waikiki is a tourist-favorite destination, home to nightclubs, hip restaurants, and upscale hotels.
- Honolulu has one of the largest Chinatowns in the U.S.
The island’s history dates back centuries when Tahitians established permanent settlements on Oahu around 500 CE. Then, in 1795 King Kamehameha I conquered Oahu and united the Hawaiian Islands. In 1845, the royal capital was moved from Lahaina in Maui to Honolulu.
Oahu was the birthplace of the Hawaiian monarchy, but by the late 19th century, the monarchy was overthrown, and Queen Liliuokalani gave up control of the islands to foreign forces in 1893. So the islands were annexed by the United States in 1898.
Also, Pearl Harbor in downtown Honolulu was attacked by Japanese forces in World War II in 1941, and 1000+ armed officials died defending the city.
Like most tropical islands, the weather in Oahu stays warm and sunny year-round, with occasional rain showers, making it ideal for people who want to settle somewhere warm.
Honolulu has hot and dry summers, and cool and windy winters, with the average temperature falling between 68-87°F. The island’s West side experiences higher temperatures and lower rainfall, and Eastern Oahu typically has more rain.
The Housing Market and Cityscape
With median sale prices falling at $1,050,000 for single-family homes and $520,000 for condos, the housing market in Oahu is fierce. Despite this, Oahu remains densely populated and accommodates the crowds with high-rise residential towers that are built throughout Honolulu.
These condo towers offer access to the city’s many restaurants and boutique shopping centers and are often a part of larger, well-developed neighborhoods.
Although the traffic situation has become horrific, Honolulu county has great infrastructure and easy access to places on foot or through the city-wide transportation system called The Bus. In addition, there are many places for families to relax and hang out, such as parks, botanical gardens, beaches, and shopping centers.
If you’re starting fresh in Oahu, the city offers many employment opportunities outside the tourism industry. Since there are thousands of job openings each year in all sectors of the economy, and salaries tend to be higher in Oahu than in other Hawaiian islands, it’s the ideal place to find a stable source of income.
So why should you move to Oahu?
Here’s why Oahu is the best Hawaiian island to live on:
- It’s a safe place for families with younger children, owing to its developed education system, secure neighborhoods, and kind locals.
- Oahu has the most amenities of any Hawaiian island.
- A wide pool of jobs are available in healthcare, education, agriculture, and more.
With gorgeous mountains, sunny beaches, and lush countryside, it’s no surprise that Maui is another favorite for visitors to the tropics. The island is also closest to the Lanai and Molokai islands, making it ideal for people who want to access them.
However, Maui is more well-known for its luxury resorts, developed towns, and high housing prices to match those of Oahu, which you can learn about from the details I’ve shared below.
Also Known As: The Valley Isle
Area: 727 square miles (second largest in Hawaii)
Population: 168,307 (2021)
- Maui is home to the Road to Hana, a 64-mile road on its East side with waterfalls, botanical gardens, and secluded beaches at every turn.
- The dormant Haleakala volcano towers over the island’s East side, at an elevation of 10,000 feet, and is a well-known site for the world’s most beautiful sunrises and sunsets.
- The island offers some of the best snorkeling in Hawaii, with abundant native marine life like dolphins, turtles, and whales on its shores.
Named after the Polynesian demigod Maui, the island was first settled around 700 A.D. by Tahitians. Maui had three kingdoms in the past that make its major settlements today; Lahaina, Wailuku, and Hana. A 14th-century Hawaiian chief built the island’s largest stone temple, Pi’ilanihale Heiau, which still exists, and an extensive road system.
In 1795, Maui was conquered by King Kamehameha I, who united the Hawaiian islands. Then, in the early 1820s, whalers, and missionaries began to arrive on the island, and although whaling declined, the sugar industry grew. That remained the island’s major means of economy for nearly a century before tourism took over.
Maui’s weather conditions vary year-round and at different places on the island, owing to its elevations and closeness to the coast. However, the climate in Maui mostly stays warm, muggy, windy, and mostly clear, and the temperature typically varies from 65-88°F.
If you’re looking for warm weather throughout the year, head to Wailuku and Kahului in Central Maui, which only gets intermittent rainfall. On the leeward side, Kihei, Wailea, Makena, Lahaina, Kaanapali, and Kapalua remain hot and dry, with the least rainfall. On the windward side of Maui, Paia, Haiku, Keanae, Hana, and Kīpahulu have heavier rainfall. Upcountry Maui is ideal for lower temperatures, where the Makawao and Kula towns experience mild temperatures and cool nights.
Housing Market and Cityscapes
The housing market in Maui is just as expensive as in Oahu, with rates ranging between $1,056,000 for single-family homes and $800,000 for condos. Its higher prices are due to the island’s many luxury hotels and resorts, which offer a tourism boom for Maui.
It’s interesting to know that Maui county consists of Maui, Kahoolawe, Lanai, and Molokai, all within accessible range from the island. As far as infrastructure goes, Maui’s roads, waterways, and streets were well in place years ago and are in dire need of repair in the present day.
Most neighborhoods have a small-town feel, with secluded ones on the island’s West and South sides. There are parks, a public transportation system, and a few high-rise buildings, which add to the island’s rustic feel. However, traffic on the Road to Hana in East Maui is rising, so it’s best to avoid it in peak tourist season.
Maui’s main source of employment is the tourism industry, as the island has many large-scale resorts and hotels. However, the island also has large sectors in agriculture, information technology, and astrophysics, offering niche opportunities for jobs.
So why should you move to Maui?
Here’s why Maui is the best Hawaiian island to live on:
- Maui is generally very safe for tourists and residents, as it has low crime rates, also making it a good place for families to stay.
- The island has retained its natural beauty despite urbanization and has clean air, water, and favorable living conditions.
- If you love off-road tours, hiking, and camping, you’ll love Maui.
The Island of Hawaii is known more commonly as the Big Island among locals since it’s the largest island in Hawaii and in the U.S. Despite the size, it’s the least populated island, owing to most parts being unreachable by land. Big Island is also home to active volcanos, with Mauna Kea and Mauna Loa being the largest, which serve as its main tourist attractions.
The housing in Big Island is less competitive, owing to lower prices and the somewhat lack of amenities available. Read on to learn more about the Big Island and why you’ll love it here.
Also Known As: The Big Island/The Orchid Isle
Area: 4,028 square miles (largest in Hawaii)
Population: 200,629 (2020)
- The island has a Volcanoes National Park open to the public, which features two active volcanoes: Kilauea and Mauna Loa.
- Big Island has gorgeous green sand and black sand beaches, Mahana Beach and Punaluu Beach, respectively.
- Its area increases each year as the world’s most active Kilauea volcano continues to pour lava into the ocean.
As the youngest Hawaiian island, Big Island was discovered by people from the Marquesas of Polynesia some 1500 years ago. The explorer Captain James Cook reached here in 1778 and was killed at Kealakekua Bay in 1779. The Big Island is also the birthplace of King Kamehameha I, who united the Hawaiian islands in 1795 and named them after his birth island.
Big Island enjoys eleven of the thirteen climates on Earth, so depending on where you land, expect heat, chill, snow, or rain. For the most part, it’s warm and tropical year-round, with average temperatures near the major resort areas being 75-85°F.
At higher elevations like Waimea, temperatures are much cooler, especially during the night. Hilo can also have lower temperatures depending on how far inland you travel and has a history of hurricanes and tropical storms. Whereas Mauna Kea, Mauna Loa, and Hualalai can be quite chilly, with snow expected in winter.
Housing Market and Cityscapes
The median sale prices on the Big Island are much lower than the other main islands, with $509,000 for single-family homes and $510,000 for condos. The major residential settlements are Hilo and Kona (the oldest town in Hawaii), which are also tourist destinations with well-maintained infrastructure, bike paths, and downtown areas with many shops.
Traffic can be a problem on the 10-mile stretch between Keaau and Pahoa in the Puna District. Aside from Kona and Hilo, other residential districts rely on rainwater systems for water and have to pick up their own mail and drop off their garbage at disposal sites.
Cattle ranching is the main contributor to the economy, and leading agricultural products include orchids, coffee, and macadamia nuts. Unfortunately, aside from tourism, there are few jobs on the island, and unemployment is high. So make sure to land a job before you arrive, choose to work remotely, or adopt a rural lifestyle through agricultural practices in the many communes.
So why should you move to the Big Island?
Here’s why Big Island is the best Hawaiian island to live on:
- Big Island is fairly safe, as neighborhoods look out for each other, and crimes are generally low.
- The island is ideal for senior citizens to settle, with Hilo housing the most retirees in Hawaii.
- Those seeking nature will love Big Island, as it has an environment uninterrupted by much urbanization.
Kauai will be your best pick if you’re looking for the most secluded and beautiful island to live on, away from crowds. The island has stunning beaches, waterfalls, and mountains on its Na Pali Coast and a rustic beauty from its lush landscapes and rainforests.
Living in Kauai is more laid-back and relaxed than the other islands, except for the housing prices, which are comparable to the larger islands. However, that shouldn’t deter you from living in Kauai, which has plenty of hidden charms which you can read about below.
Also Known As: The Garden Isle
Area: 552 square miles
Population: 73,298 (2020)
- Kauai is geologically the oldest Hawaiian island, and it’s the least developed of the four major islands.
- By state law, no building can be constructed taller than a palm tree, adding to the island’s eco-friendly environment.
- You can find the largest coffee plantation in the U.S. on Kauai, named Kauai Coffee.
Polynesians are said to have reached the Hawaiian islands a millennium ago and settled at the mouth of the Wailua River. The mythical people known as the Menehune (little people) are believed to have constructed some of the island’s landmarks. They also traded through the Menehune Fishpond, an 800-year-old water body that still exists today, by providing villagers with fresh catch.
In 1778, the English explorer Captain James Cook first landed in Kauai. Then in the late 18th century, Kauai and Niihau were the only Hawaiian islands to resist conquest by King Kamehameha I. However, they were united with the rest of Hawaii in 1810 through peaceful negotiations.
Sugar and pineapple plantations were the island’s main source of economy for 100 years, bringing people from around the world to work on them.
The weather in Kauai remains stable, warm, and humid year-round, with temperatures varying between 67-85°F. Its mountain ranges in the Kokee State Park and the Waimea Canyon are generally cooler and receive more rainfall, with Mount Waialeale averaging some 450 inches of rainfall annually, considered one of the wettest places on Earth.
Housing Market and Cityscapes
The median sales prices of homes in Kauai are on par with the larger islands, averaging $995,000 for single-family homes and $742,450 for condos. However, as the least populated island, Kauai lacks urban development (so you can’t shop for your favorite brands here.)
Kauai county governs Kauai and the Niihau island off its shore. The infrastructure was put in place decades ago, including roads, one-way bridges, small parking lots, and a small public transportation system called the Kauai Bus, which is the only way to get around Kauai. The drainage and water system is somewhat lacking, as it’s from the times of sugar plantations and has caused small-scale floods over the years.
The communities and neighborhoods have a nice relaxed vibe, and everything starts shutting down early.
Tourism rounds out Kauai’s economy, with nearly 50% of the island’s workers employed in the hospitality industry. Kauai’s top 10 employers in 2019 were resorts and hospitals, with some small opportunities for locally-owned businesses and small-scale ventures.
So why should you move to Kauai?
Here’s why Kauai is the best Hawaiian island to live on:
- Kauai’s lesser populated land makes it safe and secure, with very low crime rates.
- Kauai is one of the world’s premier hiking destinations, from the trails on its Na Pali Coast.
- The old Hawaiian lifestyle of peaceful living still resides in Kauai, and its neighborhoods are ideal for families.
Being one of the smaller inhabited Hawaiian islands, only 2% of Lanai is available for private residents to live on, as Larry Ellison, founder of the Oracle Corporation, has ownership of the rest. The island is known for its lush fields, pineapple plantations, and complete lack of urbanization, which makes it ideal for people looking for a secluded lifestyle.
However, despite the housing market being cheaper in Lanai than any other Hawaiian island, you’ll need luck to find a home here as there are hardly ever any on sale!
Also Known As: The Pineapple Island
Major Settlement: Lanai City
Area: 141 square miles
Population: 3,135 (2020)
- Lanai was once responsible for producing 75% of the world’s pineapples from its plantations.
- Lanai has one school and hospital serving the entire island.
- It’s believed that cliff diving originated from Kaunolu Point in Lanai, where Hawaiian warriors used to leap into the ocean.
Lanai was composed of small fishing villages in the past. However, in 1854 a group of Mormons formed a colony, which was later unsuccessful. Until 1922, Lanai was used primarily for cattle grazing when it was bought by the Dole Corporation for use as pineapple plantations.
In 1961, Castle & Cooke merged with Dole and took over Lanai with 98 percent ownership of the island. Here, they established luxury resorts, golf courses, and residences. In 2012, Castle & Cooke sold their ownership of Lanai to Larry Ellison for $300 million.
Lanai has pleasant and dry weather year-round, with temperatures ranging from 70-85°F. Coastal places, like Manele Bay, are usually about 10 degrees higher, while Lanai City averages 72°F. The island receives nearly 37 inches of rainfall per year.
Housing Market and Cityscapes
The sale prices for single-family homes in Lanai average at $440,000. The island has no traffic lights and has only recently seen paved roads. Ellison has proposed plans to modernize the city while keeping it eco-friendly, which include a hydroponic farm.
The island’s population is concentrated in Lanai City, which features locally-owned businesses selling art, souvenirs, and more.
You’ll need a 4WD to get around the island, as there is no public transportation. In addition, there is the expected establishment of an industrial park, a university, more housing, film studios, and a tennis academy.
Most inhabitants in Lanai work for the Four Seasons hotel or the other upcoming projects initiated by Ellison.
So why should you move to Lanai?
Here’s why Lanai is the best Hawaiian island to live on:
- Lanai is extremely safe, with no crime and as few as 22 inhabitants per mile.
- The natural beauty of Lanai is untouched by the outside world and offers quiet living amongst nature.
- There are close-knit communities, regular gatherings, and events that create a sense of Aloha.
Residents of Molokai are mostly families who have been here for many years and a few infrequent visitors, which makes it a peaceful place to live in. The island has rich soil, which most people grow produce on, jaw-dropping cliffs, and locally-owned businesses. Plus, the housing in Molokai is amongst the cheapest in Hawaii, as you’ll be living a rustic and rural life.
Also Known As: The Friendly Isle
Major Settlement: Kaunakakai
Area: 260 square miles
Population: 7,345 (2020)
- The island’s northeast coast has the highest sea cliffs in the world at 3,900 feet above the ocean’s surface.
- The island has only one hotel, Hotel Molokai.
- Molokai is the birthplace of the traditional Hawaiian dance, hula.
Polynesian settlers from Marquesas, Tahiti and other Pacific islands inhabited Molokai around 650 AD. There remained peace for ages until the 18th century, when internal conflicts occurred, causing chiefs from Oahu to take control of Molokai, which King Kamehameha would later unite into Hawaii.
In 1866, King Kamehameha V made Molokai, a leprosy colony at Kalaupapa, which held 8000 exiled lepers until 1969. Molokai also had a sugar mill for 30 years, run by Rudolph Meye, who produced wheat, potatoes, coffee, and corn for export.
The weather in Molokai is warm, humid, windy, and mostly clear. Over the course of the year, the temperature varies from 65°F in winter and up to 85°F in summer.
Housing Market and Cityscapes
The average sale prices for single-family homes are around $343,000 in Molokai, the lowest of any Hawaiian island.
There are no traffic lights on the island, one highway going from the island’s east to west side, a small bus system for public transport, and an airport.
In addition, the town life in Molokai is developed with one general hospital and community health center and nature and forest reserves.
Agriculture and tourism are the major means of employability in Molokai, although both are significantly low. Most locals run small-scale businesses and shops. Due to the residents’ fight against development and tourism, Molokai has Hawaii’s highest unemployment rate.
So why should you move to Molokai?
Here’s why Molokai is the best Hawaiian island to live on:
- Molokai has a stable education system, with public schools, a charter school, and one private school.
- Crime is non-existent in Molokai, as everyone knows everyone, and neighborhoods are close-knit.
- Molokai is a natural wonderland with state parks, protected areas, forest reserves, and white-sand beaches.
Closed off for residential purposes
Niihau, located off the coast of Kauai, is dubbed the Forbidden Isle, as it’s closed off to outsiders. You need an invitation from the Robinson family to enter the isle, who has owned it since Elisabeth Sinclair bought the island in 1864 from King Kamehameha V for $10,000.
The island is inhabited by 200+ native Niihauians, and contact with outsiders is forbidden on the island by the Robinson family in an effort to maintain the natural environment and indigenous people.
This is why no one can own real estate in Niihau, and even getting invited was impossible. Still, in recent years, you can tour the island for a hefty fee via helicopter or go hunting on safaris.
Though historically occupied by natives, and even a penal colony once used by Hawaiian monarchs, Kahoolawe is now completely unoccupied and dangerous to live in. That’s because the U.S. military used the island from 1941-90 for munitions testing and bombing exercises, which greatly damaged the ecology.
In 1994, the state government took control of the island to rid the island of unexploded ordnance and replant forests and vegetation.
What is the most affordable Hawaiian island to live on?
Of the four main islands, the Big Island is considered the most affordable Hawaiian island for residents. That’s because the Big Island has Hawaii’s lowest average cost of living, fair market rents, and relatively low yearly expenses, making it the most economical island in Hawaii.
Which Hawaiian island is the best to live on?
You can find a great permanent home from Hawaii’s four major islands, depending on what you’re looking for. Oahu offers the best employment and city life, Maui has unspoiled views and great residential communities, whereas the Big Island and Kauai offer natural wonders, lower housing prices, and a lack of crowds.
Where is the cheapest and safest place to live in Hawaii?
The islands of Molokai and Lanai offer the cheapest housing and crime-free communities. Although, finding homes and employment here can be difficult, owing to the close-knit local communities already residing here.
What is the best Hawaiian island to retire on?
Hilo on the Big Island is the best Hawaiian island for retirement. The island has the largest population of retirees in Hawaii, and the cost of living is 18% less expensive than the state average. Other than the cost advantages, Hilo has great gardens, zoos, and hiking trails.
How much money do you need to live comfortably in Hawaii?
The average local earns $58,000 each year living in Hawaii. However, the cost of living is higher on the islands than in the rest of the U.S. Ideally, families with two children need $75,000 yearly to live comfortably in Hawaii, including all amenities.
Winding Up The Best Hawaiian Island to Live on
Living in Hawaii is a dream, but the competitive housing markets here make it a harsh reality; I mean, who doesn’t like waking up every morning in paradise? However, for those that can secure employment on its islands and find a suitable home, there’s really no better place to settle permanently than Hawaii.
Each island offers natural beauty from beaches, lush mountains, and forests, low crime rates, safe close-knit communities, and a welcoming Aloha spirit, which is an ideal environment to grow up and old in.
Looking for the best Hawaiian island to live on for families? You’ll love Oahu and Maui.
Need an island to splurge your retirement funds on? Head to Hilo on the Big Island.
Want to live away from crowds and amidst nature? Then, Kauai island is the best one for you.
Want to try living a rustic life away from modern facilities? Look for a home on Lanai and Molokai islands.
Living in Hawaii is a literal dream come true!
Last Updated on April 3, 2023 by Brigitte