I like the second home better. Enclosed pool means potential year-round use (what could be nicer than a nice swim followed by hot tub in winter?). Lot is significantly bigger - over 1/3 acre. The "whimsy" is all in the decorating/furnishings, which could be yanked overnight and replaced with whatever style you prefer.
I'd have the pool inspected for leaks and proper plumbing/heating. Also check the structure around/over the pool for moisture problems/dry rot/termites. Big crack in driveway might mean ground settlement, or nothing at all.
Again, what about the laundry room???