Join Date: Aug 2011
Location: Sydney, Australia and Stockholm, Sweden
Programs: VA Platinum, SQ Gold, TK Gold, Hhonors Gold, Accor Diamond, Bonvoy Gold, Radisson Premium
Posts: 1,143
I'd rule out Polignano al Mare - the restaurant is over-rated anyway IMHO. The beaches are small and crowded, but I don't have experience with resorts there.
In your budget I'm sure you could get a private villa with pool to be nice and close to baby at all times. Maybe Croatia? You should be able to fly to Split (cheaper) or Dubrovnik (more expensive).