When two boats share the same hull type — in this case both the Key West 166 SK 2009 and the Key West 244 CC 2011 are modified vee designs with fiberglass construction — the buying decision usually comes down to a handful of practical questions: how many people are you putting on the water, how far do you trailer, and what does your tow vehicle weigh?
The power gap is worth calling out. Rated to 300 hp, the Key West 244 CC 2011 has a 250-hp advantage over the Key West 166 SK 2009's 50-hp ceiling — enough to notice on acceleration and at cruising speed, particularly with a full passenger load.
For family outings this is probably the sharpest distinction between the two. The Key West 244 CC 2011 is rated for 7 passengers, while the Key West 166 SK 2009 caps at 4. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Key West 244 CC 2011 could be the deciding factor.
Bottom line: Choose the Key West 244 CC 2011 if your priority is putting more people on the water — it handles 7 passengers and at 24,3 ft it has the deck room to back that rating up comfortably. The Key West 166 SK 2009 is the smarter pick if you want a lighter, easier-to-trailer boat rated for 4 that costs less to run day-to-day.