Turtle Mound 4, pictured from the black tees, looks impossible.  It's 130 yards with ever obstacle imaginable - first water, then sand, then a severely sloped and narrow green.  At least the palms on the back are nice to look at! 

By the way, this is the only hole on a "Hardest" list that's also on the Postcard List as one of the 18 most beautiful golf shots in The Villages!  

Hill Top 9 is a real maverick.  One of a kind.  It's only 115 from the back tees, but you often won't have a direct shot to the cup.  And the traps on the right make it hard to even pull the cord and bailout.  You end up having to use a long iron shot to stay low.  Plus, it's uphill and the green is sloped.  You won't be "cruising" on this one!  

Longleaf 4 is the perfect counterbalance to the previous 3rd hole.  Both are incredibly hard despite the 200-yard variance between the two.  The picture is taken from the black tees and while it shows the challenging over-hanging tree, it doesn't illustrate the real difficulty - the green is perched up so high that if you don't stick the landing, you'll be chipping onto a very tough multi-tiered rolling green.  Longleaf 3 and 4 is a great combo punch! 

The 9th at Mira Mesa is the only shot on the course over water.  But that's not the most difficult part of this hole.  It's the narrow, elevated green that's so tough to land.  The Caddie Tip is to club up to avoid coming up short and rolling back down toward the water.  The left side rolls away as well.  A Top Five course deserves a great finishing shot!

Hope the sight and sounds from the nearby Fenney Rec Center are soothing, because the shot on Red Fox 7 will most certainly not be.  You'll need pinpoint accuracy to land safely. The walled marsh and front door trap are easily seen.  But anything long will skip over the green's back ridge into the forest where furry creatures like Red Foxes play.  

The 2nd hole at Tarpon Boil is a really thin shot - you could even say it's pencil-thin.  The front trap covers nearly the entire green and it's crowned in the center rolling shots on either side away.  It's a "buffet" of obstacles! 

It's a real gamey start to Volusia 1.  No other starting hole in The Villages is as uphill as this.  And you better not be long or you'll be chipping right back down that hill - the good news is there's a fire station at the bottom of the hill in case you need a rescue!

The 7th hole at Volusia is the toughest shot on the course.  It's 130 yards of direct-line trouble over water and sand to a narrow, crowned green that rolls wayward shots far away.  This is no game - it's a seriously difficult shot.  

Walnut Grove 5 has more sand than green.  All in your way.  And that's why it's on this list!