Thinking about moving to Hawaii? It’s an incredible idea — but picking the right island matters more than most people realize. After living on a few islands and spending real time on all of them, I can tell you: each one has its own pace, quirks, and strengths. Some islands will fit you like your favorite slippahs, and some… not so much. Here’s a straightforward, no-fluff breakdown to help you find the best island to live on in Hawaii based on real lifestyle factors — not just travel brochures.
Understanding Hawaii’s Island Differences
Every island feels different — and it’s not just about size. Some islands buzz with energy, others move at a slow, sleepy rhythm. Some are easy on your wallet (relatively speaking), others will have you paying top dollar just to live close to a decent grocery store. Knowing the real differences up front can save you a lot of time, money, and frustration. Let’s dig in.
0704Hawaii037 by Luke H. Gordon is licensed under CC BY 2.0. Image may have been resized or cropped from original
The view of Diamond Head from anywhere is majestic, but the brown lava contrasts with the blue of Waikiki’s Pacific Ocean so beautifully.
Oahu: The Gathering Place
Affordability
Oahu is expensive, plain and simple. Honolulu’s median home prices are among the highest in the country, often hitting $800,000 to $900,000. You can find cheaper pockets if you’re willing to live further from town — places like Ewa Beach or parts of the West Side — but be ready for long commutes and heavy traffic.
Community Feel
Oahu feels busy and urban in the city, but quieter beach communities exist if you know where to look. Places like Kailua, Kaneohe, and parts of the North Shore still have strong neighborhood vibes. It’s not as easy to feel “small town” on Oahu as it is on the neighbor islands, but it’s possible if you find the right spot and settle in.
Outdoor Access
Oahu nails it when it comes to outdoor life. Surfing, hiking, snorkeling, paddling — it’s all here, often within a 30-minute drive. Even though it’s the most developed island, Oahu still offers plenty of wild beauty if you’re willing to explore beyond Waikiki and the tourist zones.
Job Availability
If you need steady work, Oahu has the most options. The job market is bigger and more diverse than any other island, with opportunities in tourism, healthcare, government, and increasingly, remote tech work. Plus, infrastructure like high-speed internet makes remote life much easier here compared to the outer islands.
View of Honolua Bay, a stunning coastal view in west Maui
Maui: The Valley Isle
Affordability
Maui is beautiful — and you pay for it. It’s one of the most expensive islands to live on, especially around hotspots like Kihei, Lahaina, and Wailea. Housing can easily top Oahu’s prices in some areas. If you’re looking for something more affordable, Upcountry (like Pukalani or Makawao) offers better value, but it’s still not cheap by mainland standards.
Community Feel
Maui strikes a balance between local and touristy, depending where you land. The South Side and West Maui lean heavily into tourism, but places like Haiku, Makawao, and parts of Wailuku keep more of a residential, island-style pace. Community life feels tight once you get involved, but it can take time to break through the tourist energy in some areas.
Outdoor Access
Maui is unreal for outdoor living — think world-class beaches, snorkeling at Molokini, epic hikes in Iao Valley, and sunrise missions up Haleakalā. Everything feels a little more spread out than Oahu, so having a car here isn’t optional — it’s essential.
Job Availability
Tourism drives most of Maui’s economy, so jobs are plentiful if you’re in hospitality, food service, or retail. Professional careers exist but are fewer and farther between. Remote workers can do well here if they’re self-sufficient and don’t mind paying a premium for island life.
West Side of The Big Island of Hawaii
Big Island: The Island of Hawaii
Affordability
Big Island wins for affordability, hands down. You can still find homes under $400,000, especially on the east side near Hilo and Puna. Even areas near Kona, though more expensive, are still cheaper than equivalent places on Maui or Oahu.
Community Feel
Big Island has a strong local vibe, and it feels more rooted and connected than the busier islands. Hilo, in particular, has a small-town, old-school Hawaii feel. Kona is a bit more transient and touristy, but still relaxed compared to places like Honolulu. Expect more aloha spirit, but also know you’ll need to respect local customs and ways of life if you want to fit in.
Outdoor Access
From black sand beaches to volcanic craters, Big Island’s outdoor scene is next level. Surfing, hiking, diving, camping — it’s all here, and with way fewer crowds. You’ll need to drive a lot — the island is bigger than all the others combined — but the raw beauty makes it worth it.
Job Availability
Big Island’s job market is limited compared to Oahu and Maui. Healthcare, education, agriculture, and tourism are the main sectors. If you’re a remote worker or don’t need a high-powered career, it’s a fantastic choice. Otherwise, expect to hustle a bit more to find steady income.
Kauai: The Garden Isle
Affordability
Kauai isn’t as expensive as Maui or Oahu, but it’s getting there. Housing prices have been climbing fast, especially post-pandemic, and options can be limited. Renting is tough too — there’s a lot of competition for long-term rentals, especially in desirable areas like Kapa’a or Princeville.
Community Feel
Kauai feels the most “small town” of the main islands. It’s quieter, slower, and incredibly tight-knit. People know each other here, and if you stay long enough, you’ll be part of the rhythm. It’s also a place where respect for local culture isn’t optional — it’s expected.
Outdoor Access
If you love being outside, Kauai is a dream. World-famous hiking trails like Kalalau, secret waterfalls, incredible snorkeling — it’s all packed into a relatively small island. Just know that the North Shore can get very wet and stormy during the winter months, so where you live matters.
Job Availability
Kauai’s job market is small and mainly tied to tourism, healthcare, and education. Remote workers who can bring their jobs with them are in the best position. Otherwise, finding well-paying, non-tourism jobs can be a real challenge here.
Lanai island as looking from Maui.
From Maui to Lanai Hawaii by Justin De La Ornellas is licensed under CC BY-NC 2.0. Image may have been resized or cropped from original
Lanai: The Pineapple Isle
Affordability
Lanai is a weird one. It’s tiny, mostly owned by one billionaire (Larry Ellison), and housing is limited. There’s not much available, and what is available is either subsidized (for locals) or luxury-priced. If you can get housing through an employer or have deep pockets, you might make it work — otherwise, it’s not the easiest island to break into.
Community Feel
Lanai feels like one small town — because it is. Almost everyone lives in or around Lanai City. It’s quiet, remote, and very tight-knit. Newcomers stick out, and it takes serious time to become part of the community. If you’re craving privacy and don’t mind a slower, almost isolated pace, Lanai could work.
Outdoor Access
Lanai has beautiful beaches and rugged landscapes, but not a ton of variety. You can drive down to Shipwreck Beach, hike the Munro Trail, or snorkel at Hulopoʻe Bay. Beyond that, it’s limited — but peaceful.
Job Availability
Nearly all jobs tie back to the two Four Seasons resorts or supporting industries (construction, maintenance, small retail). Options are extremely limited unless you bring your work with you.
North shore of the island of Molokai. Copyright forest-and-kim at Flickr.com Creative Commons.
Molokai North Shore by Forest Starr and Kim Starr is licensed under CC BY 2.0. Image may have been resized or cropped from original
Molokai: The Friendly Isle
Affordability
Molokai is one of the more affordable islands, but there’s a catch: availability. There’s not a lot for sale or rent, and what exists is basic. If you want simple living and you can make it work, your money will stretch farther here than on most other islands.
Community Feel
Molokai is fiercely local. It’s the island that has fought off big development the hardest, and it shows. Life here is deeply rooted in Hawaiian culture, and it’s very different from the tourist-heavy parts of the state. This can be beautiful — but newcomers who don’t respect the way of life won’t last long.
Outdoor Access
Molokai offers incredible, untouched beauty: towering sea cliffs, empty beaches, lush valleys. It’s the most “wild” of the inhabited islands. If you like solitude and outdoor adventure without crowds, Molokai delivers like nowhere else.
Job Availability
Job options are slim. Agriculture, small government roles, and a bit of tourism-related work exist, but most people here live simple, low-income lifestyles by choice. Remote work is your best shot if you want to live on Molokai without financial stress.
Affordability Showdown: Best Island for Budget Living
If cost is your biggest concern, the Big Island takes the win — no contest. Hilo and Puna especially offer real estate deals you won’t find anywhere else in Hawaii. Molokai also stays affordable, but with fewer resources. Oahu and Maui are the most expensive, with Kauai creeping up fast behind them.
Community Feel: Best Island for Feeling “At Home”
If you want a small-town vibe and a deep sense of community, Kauai, Molokai, and parts of the Big Island are your best bets. Oahu and Maui offer community pockets, but you’ll need to work harder to find them. Lanai feels close-knit too, but it’s very small and very isolated — not for everyone.
Outdoor Access: Best Island for Nature Lovers
Every island has amazing outdoor activities, but they feel different. Oahu has the most variety packed into the smallest space. Kauai feels the most wild and lush. Big Island has the most dramatic landscapes and the fewest crowds. If you want constant outdoor adventures without tourists everywhere, Big Island and Kauai are standouts.
Career Opportunities: Best Island for Building a Career
Oahu is the clear leader if you’re chasing a traditional career. Honolulu has the widest range of industries — from government jobs and healthcare to tech startups and education. Maui has opportunities too, mostly tied to tourism and hospitality, but it’s smaller. Big Island and Kauai offer fewer options, and you’ll need to carve out your niche or get creative if you want to climb a professional ladder there.
Remote Workers: Best Island for Working From Home
If you’re remote and bringing your own job with you, you’ve got options. Oahu makes it easy with strong internet infrastructure, lots of rental availability (if expensive), and more amenities nearby. Big Island is great if you want space and peace — but you’ll need to make sure the house you rent or buy actually has reliable internet (don’t assume!).
We have a couple of great resources discussing Internet in Hawaii:
Maui sits somewhere in the middle — stunning scenery with decent connectivity if you pick the right area.
Slower Life: Best Island for Simplicity and Peace
Molokai wins here, hands down. It’s slow, real, and completely different from the touristy side of Hawaii. Kauai and Big Island also offer slower, more rural lifestyles, depending on where you land. Lanai is peaceful too but so isolated that it feels almost disconnected from the rest of Hawaii.
Final Thoughts: Choosing the Best Island to Live on in Hawaii
Choosing the best island to live on in Hawaii isn’t about picking the postcard you like most — it’s about what fits your life best. Oahu is for the career-focused and city-lovers. Maui blends natural beauty with high-end living. Big Island offers space, affordability, and raw adventure. Kauai gives you small-town charm and endless greenery. Lanai and Molokai are for those who really want to live quietly and simply.
No island is perfect. Each comes with trade-offs. But if you’re clear on what you want — whether it’s career opportunities, community connection, nonstop outdoor adventure, or just peace and quiet — there’s an island waiting for you.
FAQs About Choosing the Best Island to Live on in Hawaii
Is it cheaper to live on the Big Island or Maui?
The Big Island is significantly cheaper than Maui. You’ll find lower home prices, cheaper rent, and a generally lower cost of living, especially on the Hilo side.
Which island has the best healthcare access?
Oahu has the best healthcare facilities, including top hospitals like Queen’s Medical Center. Maui and Big Island have decent hospitals, but options are more limited the smaller or more rural you get.
Where can I find the strongest local community?
Kauai, Big Island, and Molokai offer the strongest sense of local community. These islands move slower and hold tightly to traditional values, making them ideal if you want to really integrate into island life.
Is remote work possible from all Hawaiian islands?
It’s possible, but easier on some islands than others. Oahu, Maui, and much of the Big Island have reliable internet. Kauai does too, but more remote areas on all islands can have spotty service.
Which island is best for raising a family?
Oahu offers the most schools, activities, and healthcare options for families. However, many people also love raising kids on Kauai and Big Island for the slower, safer lifestyle and strong sense of community.
What do you think?