Where to Stay on Maui

Where to Stay on Maui

A Neighborhood-by-Neighborhood Guide for Future Homeowners

By Benjamin Finnerty | The 808 Team at Keller Williams Realty Maui

If you’re reading this, chances are you’re not just planning a vacation—you’re thinking about making Maui home. Maybe you’ve been here before and fell in love with the sunsets over Makena, or maybe you’re exploring the island for the first time with an eye toward putting down roots. Either way, knowing the personality of each area is one of the best things you can do before you start your property search.

I’ve lived and worked on Maui as a REALTOR® for years, and I’ve surfed, eaten, and explored my way through every corner of this island. Here’s my honest, boots-on-the-ground take on Maui’s most popular neighborhoods—and what it’s really like to live in each one.

South Maui: Kīhei

The Vibe

Kīhei is where I call home, so I might be a little biased—but there’s a reason so many residents and buyers gravitate here. It’s sunny nearly every day (South Maui gets the least rainfall on the island), walkable along the coast, and packed with great restaurants, farmers markets, and local shops. It feels like a real community without the resort price tag.

Who It’s For

Kīhei is ideal for first-time buyers, remote workers, retirees, and anyone who wants everyday beach access without a luxury resort budget. Condos here offer some of the best value on the island, and many are in complexes that allow short-term rentals—a big consideration for buyers looking at investment properties.

What to Know

The area ranges from the quieter, more residential North Kīhei to the bustling South Kīhei strip near Kalama Park. If you want walkability to shops and nightlife, South Kīhei is your spot. If you want more peace and proximity to the Kealia Pond wildlife refuge, head north.

➤ Kīhei is one of the most active condo markets on Maui. If you’re curious what’s available right now, reach out and I’ll send you my curated list of properties that match your goals.

South Maui: Wailea & Makena

The Vibe

Wailea is Maui’s resort coast—think championship golf courses, five-star hotels, and some of the most beautiful beaches on the planet. Makena, just south, is quieter and more rugged, with Big Beach drawing locals and visitors alike. This is premium real estate, and it feels like it.

Who It’s For

Luxury buyers, second-home owners, and those who want a resort lifestyle year-round. Properties here range from high-end condos at places like Wailea Beach Villas to sprawling single-family estates with ocean views that will take your breath away.

What to Know

Wailea’s HOA fees tend to be higher, reflecting the resort-level amenities. But the trade-off is world-class pools, concierge services, and beautifully maintained grounds. Makena is more limited in inventory but offers a sense of seclusion that’s hard to find elsewhere on the island.

➤ Interested in Wailea or Makena properties? I can walk you through the differences between complexes and help you find the right fit for your lifestyle.

West Maui: Lahaina

The Vibe

Lahaina holds a deeply special place in the hearts of everyone on Maui. The historic town is in the midst of rebuilding and renewal following the 2023 wildfires, and the community’s resilience and aloha spirit have been incredible to witness. As Lahaina continues to rebuild, there are opportunities to be part of this next chapter.

Who It’s For

Buyers who feel a connection to Lahaina’s history and want to invest in its future. This area appeals to those who value community, culture, and being part of something meaningful. It’s also historically been one of the more affordable West Maui options compared to Kāʻanapali and Kapalua.

What to Know

The real estate landscape in Lahaina is evolving. I’d encourage anyone interested in this area to have a conversation with me so I can share the most current information on what’s available, what’s being rebuilt, and how the market is shaping up.

➤ Lahaina’s story is still being rewritten. If you want to be part of it, let’s talk about the opportunities available in this resilient community.

West Maui: Kāʻanapali

The Vibe

Kāʻanapali is the quintessential West Maui resort experience. The famous Kāʻanapali Beach stretches for three miles, lined with resorts and condo complexes. There’s great snorkeling at Black Rock, Whaler’s Village for shopping and dining, and those legendary West Maui sunsets every single evening.

Who It’s For

This area attracts vacation-home buyers and investors looking for strong rental income potential. Many condo complexes here are zoned for short-term rentals and are located in business-zoned areas—which means they are not affected by Bill 9, the recent legislation impacting short-term rentals in apartment-zoned properties. That’s an important distinction for investors.

What to Know

Prices here sit between Kīhei and Wailea. You’re paying a premium for the West Maui location, but the rental income potential can make the numbers work beautifully for the right property. The key is understanding which complexes offer the best return—and that’s where having a local agent makes all the difference.

➤ Thinking about an investment property in Kāʻanapali? I can help you run the numbers and find complexes that align with your investment strategy.

West Maui: Kapalua

The Vibe

Kapalua is the crown jewel of West Maui—exclusive, lush, and breathtakingly beautiful. Home to the Kapalua Resort, two championship golf courses, and some of the island’s most pristine beaches (Kapalua Bay has been rated one of America’s best beaches more times than I can count), this area feels like its own world.

Who It’s For

Discerning luxury buyers who want privacy, natural beauty, and top-tier amenities. Properties here often come with golf memberships, and the Kapalua community has a distinct, refined character that attracts buyers from around the globe.

What to Know

Inventory at Kapalua is limited and doesn’t turn over often, which means when the right property comes on the market, it moves fast. If Kapalua is on your radar, getting set up with instant alerts for new listings is essential.

➤ Want to know the moment a Kapalua property hits the market? I can set you up with instant MLS alerts so you never miss an opportunity.

Central Maui: Kahului & Wailuku

The Vibe

Central Maui is where the locals live. Kahului is the island’s commercial hub—Costco, Home Depot, the airport, and the harbor are all here. Wailuku, just next door, has a charming small-town feel with a growing food and arts scene along Market Street. These aren’t resort towns, and that’s exactly the appeal for full-time residents.

Who It’s For

Full-time residents, families, and anyone looking for a more “normal” lifestyle on Maui. Central Maui offers the best access to schools, hospitals, and everyday conveniences. If you’re relocating to Maui for work or raising a family, this is where most of the practical infrastructure lives.

What to Know

Single-family homes here are in high demand and represent some of the best value for full-time living. Central Maui doesn’t have the beach-town glamour, but it has something equally valuable: convenience, community, and a real sense of place.

➤ Looking for a home base on Maui? Central Maui might surprise you. Let me show you what’s available in Kahului and Wailuku.

Upcountry: Makawao, Pukalani & Kula

The Vibe

Upcountry Maui is like a different island entirely. Perched on the slopes of Haleakalā, you’ll find rolling green pastures, cooler temperatures, and a bohemian-meets-paniolo (Hawaiian cowboy) culture that’s unlike anywhere else in Hawaiʻi. Makawao town is home to art galleries, boutiques, and some incredible restaurants. Kula is all about farms, gardens, and sweeping views that stretch from the mountain to the ocean.

Who It’s For

Buyers who prioritize space, privacy, and a connection to the land. If you dream of acreage, a gentleman’s farm, or simply waking up above the clouds, Upcountry is calling your name. This area also appeals to families looking for the highly regarded King Kekaulike school complex.

What to Know

Properties Upcountry tend to be larger and more spread out. You’ll trade beach proximity for elevation, cooler weather, and some of the most spectacular views on the island. The commute to the beach is about 20–30 minutes, which many residents say is a small price to pay for the lifestyle.

➤ Dreaming of acreage and mountain views? Upcountry living is something special. Let me know what you’re envisioning and I’ll help you find it.

North Shore: Paia & Haiku

The Vibe

Paʻia is Maui’s surf town—colorful, eclectic, and full of character. It’s the last stop before the road to Hāna and home to some of the island’s best boutiques, restaurants, and people-watching. Hāʻiku, just inland, is lush and tropical with a tight-knit community and properties that range from modest cottages to sprawling jungle estates.

Who It’s For

Creative types, surfers, remote workers, and anyone who wants to live at a slower pace in one of the most beautiful settings imaginable. The North Shore attracts a younger, more adventurous demographic, though you’ll find everyone from retirees to young families.

What to Know

The North Shore gets more rain than South and West Maui, which keeps everything impossibly green. Properties in Hāʻiku often sit on larger lots and offer incredible privacy. Paʻia is walkable and vibrant but can feel touristy during peak hours—the real magic happens in the mornings before the crowds arrive.

➤ The North Shore has a magic all its own. If it’s calling to you, let’s explore what’s on the market.

A Note on Short-Term Rentals & Bill 9

If you’re considering a Maui property as an investment, it’s important to understand Bill 9, recent legislation that impacts short-term vacation rentals in apartment-zoned areas. Here’s the key distinction: condos in apartment-zoned complexes are affected by the new restrictions, while properties in business-zoned areas (many of the popular resort complexes in Kāʻanapali and Wailea) are not affected.

This is a nuanced but critical detail that can significantly impact your investment strategy and returns. I stay on top of every development with this legislation and can help you understand exactly which properties are affected and which aren’t.

Ready to Find Your Place on Maui?

Every neighborhood on Maui has its own personality, and the right one for you depends on your lifestyle, budget, and what you want your daily life to look like. The best way to figure that out? Let’s talk.

Whether you’re just starting to explore or you’re ready to make a move, I’d love to help you find your place on this island. I live here, I work here, and I know these communities inside and out.



Benjamin Finnerty

REALTOR® RS-83812

The 808 Team | Keller Williams Realty Maui

📱 808-481-9748

📧 benjamin@the808team.com

🌐 benjamin.the808team.com