On every other island the where-to-stay question is about trade-offs between areas. On Molokaʻi it is mostly about availability. There are no resorts, no chain hotels and only a small number of condos and houses that rent to visitors, so the first constraint is what exists on your dates rather than which side you prefer.
Book earlier than instinct suggests. On a normal island, leaving accommodation until six weeks out costs you money. Here it can cost you the trip.
See what is available on Molokaʻi
Kaunakakai: the practical answer
The main town, such as it is: a few blocks with the grocery, the harbor, the bakery and most of the island's restaurants. Central on a long thin island, so nothing is more than an hour away.
This is where most visitors stay and it is the right default, particularly on a first trip or a short one. It is not scenic. It is close to the things you need daily, which on an island with this little infrastructure matters more than a view.
The west end: space and sunsets
A small cluster of condos near Papohaku, dry and open, with three miles of usually-empty beach and sunsets over Oʻahu. The quietest place to stay on an island that is already the quietest in the state.
Twenty-five minutes or so back to Kaunakakai for food, which you will do more often than you expect. Bring groceries with you when you come out.
Right for a slow week and for anyone whose reason for choosing Molokaʻi was solitude. Wrong if you would rather walk to dinner.
The east side: beautiful and impractical
Scattered houses along the shoreline road toward Hālawa, past fishponds and churches, with the best scenery on the island outside your door.
There is essentially nowhere to buy food out here, the road narrows considerably at the far end, and driving it after dark is not enjoyable. If you stay east, shop in town first and plan on cooking.
Worth it for a repeat visit or for a trip built around Hālawa. A lot of friction for a first three days.
What you will not find
No resort, no spa, no concierge, no room service, no pool bar. The west end resort closed years ago and did not reopen.
Most places are self-catering, which means the grocery in Kaunakakai is part of your itinerary rather than an errand. Its selection and its hours are both smaller than you are used to.
None of this is a complaint. It is the reason the island is what it is, and it is worth understanding before booking rather than after arriving. Visiting respectfully matters more here than anywhere else in Hawaii.
The short version
First visit, three or four days: Kaunakakai.
Solitude and sunsets: west end.
Repeat visit, built around Hālawa: east side.
Any trip at all: book the car at the same time as the room. Both run out.
