Population of Luhaina is too small for a geo play IMO but I would say 300 is a fair price for it if you try to do outbound you may be able to get hight xxx to low xxxx IMO.
For vacation destinations, you can't compare the city population to the tourist population.
This isn't my niche to appraise, but find it interesting OP registered this domain for 3 years and is only looking for ~$300. The hopeful expectation is to have a 1% sale thru rate, with hand registrations expecting less than 1%. So for OP to price this domain at 10% his total cost, it certainly is priced to sell, but 3 years of registration usually means the seller is willing to wait for a decent sale.
According to
budget your trip, the average price of a hotel room in Lahaina for one night is $524.
Granted, higher end Lahaina hotels tend to be just outside of Lahaina in resort towns such as Kaanapali, Napili, and Kapalua. But still close enough to Lahaina to be largely related to Lahaina.
If a hotel chain is interested in this domain I could see it selling for XX,XXX+. (Unicorn for this type)
If a vacation rental company is interested, I could see it selling $X,XXX+. (End-user)
If an AirBNB host is interested, I could see it selling for $XXX+. (Hobbyist)
If a domainer is interested, I could see it selling for $XX+. (Reseller).
Since the domain is registered for 3 years, I wouldn't rush to try and sell it to another domainer for $XX, as $XX may be less than OP likely paid.
This domain might be hard to pitch to a unicorn hotel chain, I would think OPs best bet is to list it for low $X,XXX OBO (or best offer) while he outbounds it to Lahaina Vacation Rentals / Airbnb owners.
