Really depends on what you are looking for.
1. None of the Hilton properties are convenient to Mallory Square, action on Duval; LONG walk from Casa Marina or Reach, DT's free shuttle makes it a viable option.
2. Echo BrlDsquise's comments regarding HGI, Hampton inferior location, street noise concern; have not stayed at either.
3. Reach is still basically an upgraded motel - small rooms, exterior hallways. Would not bother.
4. Most KW beaches are meh, shuttle in the case of DT.
5. As BrlDsquise mentioned above,Casa Marina's grounds (pools, food and beverage) are by far the nicest, most true resort "feel" of the group; Doubletree is still respectable - pool bar is typically a fun place to hang out. I believe Reach guests have access to the Casa Marina grounds.
6. DT offers the best Diamond breakfast benefit - Casa Marina will nickel and dime you, no recent Reach experience.
7. Diamond suite upgrades are much more likely at DT than Casa Marina.