Casa Dolphina in Saint Petersburg/Tampa FL. 6br $125/room/night after tax. Pool and hot tub on water. Not too walkable, but near stuff. 5 ba. Most rooms have a view. Tampa activities, per Tripadvisor.
All options evaluated
Flight to Kahului 6 hours @ 488 via Alaska.
Flight 11 hours @ $560 via Jetblue per Google Flights.
Oceanfront condo on Seven Mile Beach. 3br $330/room/night after tax. "Biggest pool on Seven Mile Beach." "One of the largest patios on SMB." Rooms small/spartan but amenities would be well-utilized. Looks pretty walkable?
Flight 7 hours @ $200-250. Average February high 75 degrees, low 64.
Flight 3 hours @ $300 probably. February weather averages high of 66 degrees, low of 51. Actual temps during our window in 2019 a bit grim, especially for swimming.