The short version
Who can skip it, the family car, Turo, the Hāna and Haleakalā rules ↓
Someone staying beachfront in Wailea or central Kāʻanapali who plans to use the resort, nearby restaurants and organized tours can skip the car.
Kīhei, Nāpili, Kapalua, the North Shore, Upcountry and vacation rentals are all much easier with one.
The car-free trip looks like this: airport transfer, a Wailea or Kāʻanapali resort, beach, pool, restaurants, a lūʻau and one or two organized excursions. Resort shuttles and rideshare cover short trips, but don’t rely on rideshare somewhere remote where the ride back becomes the problem; the Maui Bus is transport, not a way to sightsee. If nobody wants to drive Hāna, take a guided tour rather than renting a car for it.

Kaupō, East Maui. Photo: Hawaii Tourism Authority (HTA)
A midsize crossover for a family of four. It has room for luggage, a stroller and beach gear without being awkward in small beach lots or on the Hāna Highway.
Choose a minivan for:
A Jeep is rarely the practical family choice.
We’d usually keep the car for the whole trip, and book early for busy periods.
Yes, with conditions.
The rental center and pickup rules: Maui airport guide →

Keʻanae, on the Hāna Highway. Photo: Hawaii Tourism Authority (HTA)
A normal sedan or crossover is fine for the standard paved Road to Hāna. Don’t assume the rental contract allows:
Check the actual contract rather than online assurances about what “most companies” allow.
Drive it or book a tour: Road to Hāna: drive yourself vs guided tour →
A standard vehicle is fine for the paved summit road; four-wheel drive isn’t needed. Use lower gears on the way down and obey the speed limits. Use the pullouts, don’t stop in the road, and let faster traffic pass.
The summit: Haleakalā guide →

Back road in Kaupō, East Maui. Photo: Hawaii Tourism Authority (HTA)
Drive times and parking: Getting around Maui → Where to base the week: Where to stay on Maui → Kāʻanapali without a car: Best things to do in Kāʻanapali →
Keep it simple and rent the car. It may sit for two days, and it’ll save the other five.
Most visitors do: beaches, Upcountry, the North Shore, Haleakalā and Hāna are spread out, and a car lets you change beaches when conditions shift. Only a resort-centered stay in Wailea or central Kāʻanapali works well without one.
Yes, if you’re staying beachfront in Wailea or central Kāʻanapali and the plan is the resort, nearby restaurants and organized tours, with airport transfers and resort shuttles. Anywhere else, rent one.
It can be, with a well-reviewed host, clear pickup and return instructions that follow airport rules, insurance terms you understand and real savings. For a late arrival, young kids or a small price difference, use an on-airport company.