I would let price and times be your determining factor. All else the same, I'd go with the one that best fits your rewards situation. After that, I'd agree with HI air and suggest Alaska Air. I'd particularly suggest you look at AK air because sometimes they're a lot cheaper on first class. You're listed in FL, how are you getting to LAX? The reason I ask is that if you're flying there you might be able to get it all as one ticket and that may affect your best choices. AK air and AA are particularly good choices out of MCO in my experiences there. You can do 1 layover as part of a single trip, I thin it's up to 30 days. If you're visiting any other island, you may be able to fly into one island and out of another though I don't think you can do a layover AND an open jaw both on the same ticket. Do rent a car for that location. Good luck and enjoy.
When I booked last January for this past August I booked the cheapest flights I could find for our overall itinerary
(with flight times & durations that I was happy with - sometimes the total flight durations to/from the east coast can vary from 12 or 13 hours to over 20 hours with layovers so you have a lot to consider). I ultimately ended up booking a combination of 3 diff. airlines (AK, Delta and Hawaiian) as we were stopping in LA to visit DL for a few nights and then were island hopping to Maui for a few nights. From DC I found that Alaska Airlines had both reasonable fares and good timing (esp. on their return from Maui).
And to add to what Dean has already mentioned, Alaska's first class prices into National Airport on the return flight from Maui were cheaper than United's coach seats into Dulles!! I still booked coach 'cuz it was cheaper but only by about $300 or so per person (but that added up to $900 for our family of 3)!! That price gap between coach and first class DID widen as time went on tho so I would book ASAP again. I booked 7 mo. out (right after I booked Aulani) and the total amount for our same flights went up by about $600 the closer we got to our trip dates.
Sadly, 8 days before we were to leave this past summer my DS had a medical emergency and wasn't allowed to fly for several weeks so we had to cancel the whole trip and we drove to FL instead. Each airline had a diff. cancellation policy and since the flights I'd booked were of the cheapest non-refundable type we had lots of re-booking issues to deal with. Delta gave us 1 yr. from the orig. purch. date to re-book someplace
AND FLY with no penalty fees (so we're heading to WDW over MLK weekend because I wasn't about to waste that $816). Hawaiian Air gave us 1 yr. from purchase to re-book (but not necessarily FLY), again, with no fees and Alaska Air (our most expensive flights) charged us $100 pp penalty BUT they gave us 1 year from our first flight origination date to use them (August 3rd in our case). Additionally, they said it is common to give a 30-day extension on that 1 yr. whenever we go to re-book (I just need to call and book by phone) so we basically have $2,000 coming to us so that we can attempt to re-book the whole trip for this August.
Even tho they charged us $100 pp for the change I was THRILLED that we would not lose the entire $2,200 that we'd spent because there was no way we could've used it by January. Now, we still have to decide if we're going to include Maui next time and we have to re-purchase that hop from LA to HNL (the Delta flight) which I am hoping to find for around the same amount on SOME airline but at least we can try to re-plan the trip. I would gladly book Hawaiian OR Alaska air again if they happen to offer the best fares / times to suit us.