Hawaii vs San Diego Airbnb: Which Market Actually Pays

San Diego runs 18 points higher on occupancy and generates £15K more median revenue per listing. Here's what that gap means for your buying decision, and the one case Hawaii wins.

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The number that settles this comparison before you've read another word is occupancy: 48% in San Diego against 30% in Hawaii. That's not a rounding difference. At Hawaii's nightly rate of $362, that gap costs you roughly $22,000 in gross revenue every year on a single listing, and the data backs that out almost exactly — median annual revenue is $37.0K in San Diego versus $21.6K in Hawaii.

This piece will work through what drives that spread, whether Hawaii's rate premium closes it, how the seasonal shapes affect cashflow for different operator types, and where regulation adds friction for a buyer arriving fresh to either market. The short answer is San Diego. The longer answer is that Hawaii still makes sense for one specific kind of buyer, and it's probably not you.

Where the money actually is

Hawaii's $362 nightly rate beats San Diego's $348 by $14. That sounds like an advantage until you pair it with occupancy: Hawaii sits at 30%, San Diego at 48%. Run those numbers across a year and the Hawaii listing earns $21.6K; the San Diego listing earns $37.0K. The rate premium is real. It just doesn't survive contact with the occupancy deficit.

The supply picture reinforces this. Hawaii carries 23,973 active listings against San Diego's 9,600. More than twice the competition for fewer booked nights. The entire-home share is similarly high in both markets — 93% Hawaii, 88% San Diego — so you're not competing against a different product type; you're competing against near-identical listings for a guest pool that, in Hawaii, simply isn't booking as often.

Both markets saw enormous rate growth year-on-year, 63.8% Hawaii and 65.0% San Diego, so neither has a momentum edge on pricing. What the data can't tell you is purchase price or mortgage cost in each market, and that's the honest caveat: a Hawaii property bought at the right number on the right island could change the yield calculation entirely. But on operator economics alone, San Diego wins without much argument.

The shape of the year

Both cities peak in July, but they behave very differently across the rest of the calendar. Hawaii runs from a 30% trough in May to a 54% peak in July — a 24-point swing, and a trough that lands in what most buyers assume is peak spring season. San Diego moves from 31% in December to 68% in July, a 37-point swing, but its floor is in winter rather than spring, which is a more intuitive pattern to manage cashflow around.

For a year-round operator, San Diego's floor of 31% is barely any worse than Hawaii's 30%, but its ceiling of 68% is 14 points higher. If you're running a single property and need consistent monthly income to cover finance costs, San Diego's occupancy curve is simply more forgiving. Hawaii might suit an operator who plans to block personal use in May and doesn't need the rent to cover costs every month — which is exactly the profile of someone who bought the property for lifestyle reasons and lets it out around their own visits. That's a legitimate strategy. It's just not an investment-first strategy.

Where the rules bite

Neither market imposes a night cap as of the latest snapshot, which removes the single biggest structural risk for a short-let investor — the kind of cap that's gutted returns in Edinburgh and parts of London. That's genuinely good news for both cities and means you're not buying into a market where the council can halve your revenue with a single policy vote.

The caveat is that 'no night cap' is a market-level data point and doesn't capture HOA restrictions, condo rules, or city-district-level ordinances that can effectively bar short-term letting in specific buildings or zones. Hawaii in particular has seen aggressive municipal action on individual islands — Maui's 2023 moratorium on new permits in certain zones is the obvious example — and a buyer needs to verify permit status at the property level before exchanging, not after. San Diego has its own permitting regime, but the regulatory trajectory there has been more stable. Neither market is risk-free on this front; both require a solicitor or local attorney who knows short-let law specifically, not just conveyancing.

The call

San Diego is the better investment market. The occupancy gap is too wide to paper over with a $14 rate premium, the supply environment is more rational with fewer than 10,000 active listings, and the seasonal shape produces a more manageable cashflow year. A buyer whose primary goal is generating income from a property they don't already own should shortlist San Diego and not spend much time on Hawaii.

Hawaii wins one scenario: you're buying a property you want to use yourself, the letting income is supplementary rather than load-bearing, and you've done the permit diligence on a specific island and property type. In that case the lower occupancy is acceptable because you're occupying the property during the troughs anyway, and the $362 nightly rate is competitive when you do let. That's a sound approach for the right buyer. It's just a different business from income-led investment, and conflating the two is how people end up disappointed on both counts.

Frequently asked questions

Methodology. Figures are medians across active listings from Inside Airbnb's 2026-06-21 snapshot, refreshed automatically as new snapshots land. The table and chart above always show the latest data; the commentary is re-written when the numbers move materially.