Hmm. I honestly can't vote yet. I've played all the games on this list, but the qualification of "enjoyment" is tricky. One thing I know for sure is that Castlevania 64 and Legacy of Darkness are the best 3D Castlevania games and can still be enjoyed on repeat plays longer than the others. (So those two are definitely VERY enjoyable*see end of post). Also, Lament of Innocence is better than Curse of Darkness (not to say that CoD doesn't have redeeming factors like its camera system). Judgment--does it even count? I mean, it's a side/concept/novelty game like The Arcade. It can be amusing, despite its faults. Lords of Shadow is almost just as a weird beast in some ways. And I'm tempted to say it's the most disappointing because it had next-gen resources and had a number of 3D examples to use as reference for refinement. Not to mention that it felt like a roughly 85% Hollywood distortion of Castlevania. I've tried replaying it on numerous occasions--as recently as two or three days ago, and its problems become more glaring. While I had begrudging fun with it the first time through, I find it a very constricted, boxed in game. CoD was monotonous hallways, but LoS feels like it's made of restricted set pieces that feel mechanically broken and it's hard to know where you can and cannot go. For example, the huge ogre that smashes out of the fortress. When it starts that, the game stutters and then you get into these segments where you can't move forward until it gets done with a set amount of animations, even though little goblins are attacking you and there is a two-foot-tall obstruction blocking your path that would be easy to jump over. The game is filled with these moments. It feels so gimmicky and slapdash, despite some truly excellent visual flourishes/vistas. The jumping mechanics themselves feel so ridiculously loose that they were never intended for any serious platforming based on the player's choice/skill (a key CV concept). The game just doesn't trust the player, making it almost as guilty as the fundamental arena/hallway flaws of LoI and CoD. There's absolutely nothing with the skill-based freedom and dynamic structure of, say, Level 2 of CV64. LoS is still too obsessed with overzealous and superfluous combos. I mean, it doesn't even feel as open in design as God of War.
So, all that said, the battle is between Curse of Darkness, Castlevania Judgment, and Lords of Shadow. Judgment is so niche and irrelevant that I don't think I can blame it. So, CoD and LoS are left... CoD was a few steps forward and twice as many steps backward from LoI, which doesn't bode well for it. But LoS was supposed to be the relaunch and big solution to 3D Castlevania, but rather than trying to be more in the vein of CV64/LoD, which had a lot of things working for them, it brought in several of the pitfalls of LoI/CoD and just made them seem more fancy in presentation while doing random, inconsequential name drops of Castlevania lore. On the other hand, LoS in of itself is not a terrible game when compared to everything else out there. But, if we change "least enjoy" to "most disappointing," LoS is kind of the winner by analysis. CoD was a disappointment for sure, but the fact that LoS could only get around LoI level when all is said and done is kind of sad. Still, I'll hold off my vote and think it through some more. Basically, I find the least faults with CV64/LoD, and every 3D game after those was enjoyable in their own ways the first time through, but none of them hold up or really clearly made the case for best 3D Castlevania.
*Those N64 games had a lot of positive/innovative features that served up CV in 3D:
*Multiple unique characters (up to four in LoD, two in CV64) with alternate levels/bosses
*Full 3D gameplay (ala Mario 64, so it's not "on-rails")
*Multiple endings based on performance
*Level Design features spatial depth (vertical and horizontal--not flat hallways)
*day-and-night cycles with time-sensitive events (like Simon's Quest)
*Weather effects (rain, lightning, moving clouds, and "fog"--the last one likely being a graphical shortcoming that actually helped)
*Dynamic, real-time lighting (next to candles, for instance)
*spot-on atmosphere
*death-defying platforming of all sorts (including ledge grabbing).
*environmental/enemy hazards (medusa heads, spikes, guillotines, buzz-saws, cannons).
*innovative survival-horror/suspense elements
*Vampires that pretend to be human and vampires as regular enemies besides bosses
*status changes, including poison and vampirism
*manageable questing with inventory items (meat, keys, cards, cure ampules, etc)
*interesting, involving plot (characters like Rosa, Vincent, Renon, Malice, Henry, etc)
*3D in-game cinemas
*Some voicing
*Unlockable alternate costumes
*Long and short-ranged attacks (IE: whip + sword)
*upgradable sub-weapons (in LoD)
*There is a useful slide and duck/crawl play mechanic
*Diverse mix of old and new enemies in 3D
(As an aside, it's worth noting that certain Beta video elements didn't get into either game like swinging over gaps with the whip; but it shows that minds were in the right place)