If you're looking for a meeting place or a good stop around ½ or halfway between Hollywood and Cutler Bay, you can try Westchester, FL, which is about half an hour southwest of Hollywood, or about half an hour north of Cutler Bay.
Another possible place to stop near the midpoint is River Park Trailer Park.
About ⅓ or a third of the way, you can stop at West Little River, FL. This is about 17 minutes southwest of Hollywood.
About ¾ or three fourths of the way, you can stop at Kendall, FL. This is about half an hour southwest of Hollywood, or about 14 minutes north of Cutler Bay.
If you drive straight through without stopping at all, the total distance is 43 miles. The distances shown above don't include local roads to get into each town, so if you're planning a long road trip, make sure you factor in traffic and road conditions, rest stop breaks, and interesting detours along the way. If you're in a rush, you can do the trip with zero stops, and your total travel time would be around 53 minutes.