It's really hard to rank them, but here's my best shot, with my reasons for each ranking. I also included some that are now HVC, but we stayed there in the Diamond days:
1. King's Land Waikoloa - the best location and resort in the best destination
2. Kohala Suites Waikoloa - second best resort in the best destination
3. Charleston Liberty Place - the best furnished and appointed villa we have stayed at. Excellent location.
4. Tuscany Borgo alle Vigne - unique resort in a beautiful, unique destination. Lots of "vino"
5. Ocean Oak Hilton Head - great location on a great island
6. Lagoon Tower Waikiki - great property, but a somewhat lower ranking because I'm not a big city/urban guy
7. Fiesta Americana Los Cabos - great grounds in a great destination, but rooms were dated when we were there
8. Carlsbad Marbrisa - Fine location but unremarkable
9. Orlando Tuscany Village - it's Orlando. Meh.
10. Orlando Sea World - it's Orlando. Meh.
11. HVC Kaanapali Beach - owned here until 2014 pre-HVC. It's in Maui, but not really on the main Kaanapali Beach
12. The Point at Poipu, HVC - stayed here pre-HVC. A little dated. On the water but no beach.
13. The Ridge on Sedona - stayed prior to HVC. Dated rooms, but good location
14. Las Vegas Elara - it's Vegas, Double Meh.
Upcoming. We'll see where these rank:
- La Pacifica Los Cabos
- The Bay Club Waikoloa