I have played Negril Hills many times. It is in decent shape for the type of resort it is. It could used a re-design IMO because there are places where the layout just doesn't make sense. Overall it is well maintained and on par with an average public course at home.
The Tryall course is not too too far way. You will pass it on your way to the resort. It is expensive compared to the included golf at Negril Hills, but it is a nicer course. We tend to just play at Negril Hills with the included greens fees and free transport.
I always play in the morning. The bus leaves CN at around 8AM and sometimes stops to pick up players from CSA as well. You can play in under 4 hours most of the time, but if you get done too quick the bus won't be there to take back for a bit, so don't rush.
No need to book tee times in my experience. That could vary at times but we have never booked a tee time.
Our caddy this past summer was a very nice young man named Shern. He is polite, helpful, knowledgable and fun to be around. Be sure to get your caddy something to drink whenever you get something and tip them well as they only get a portion of the caddy fee.
My husband and I have played Negril Hills many times as well. Last year we got 6 rounds (5 nine holes and once 18 holes). The course has undergone many improvements over the past several years. Last year they made a real effort in cleaning up the greens.
We prefer to play our nine holes of golf in the afternoon - we enjoy sleeping in a bit and then doing acquabics in the morning.
The shuttle leaves around 1:00 PM and gets you back to the resort just after 4:30 PM - back in time to relax around the swim-up bar!
As far as booking tee times goes, I would not worry about it, all you need to do is go to the concierge desk and let them know that you want to take the golf shuttle. They will give you a ticket that covers the cost of your green fees.
Over the past several years our caddies have been Shaaron and Steacie - excellent caddies, lots of fun.
The one thing that I like about Negril Hills is that you can request caddies when you come back for a second or third round of golf - just make sure that you let Miss Mary know that you are coming back and who you would like for your caddie.
We walk the course, and it is truly very very hilly. It has some wonderful views from the tee-boxes and greens, so bring a camera along.
If you have any more questions let me know - we are back to CN on 28 Feb and can't wait to start playing golf again - hitting the golf ball indoors is not the same.
One last thing - we also asked if we could store our clubs there for our visit, and there was no issue. It was very nice to be able to walk back to our room with no clubs or golf shoes!
Other great caddies are Rockie and Ronicka as well.
Rule of thumb is a dollar per hole (I am thinking in US dollars because that is what I use). Most folks tip $10 for 9 holes and $20 for 18 holes. Since the caddies only get a small portion of what the courses in Jamaica call the "Caddie Fee" they are mainly working for tips.
All the best-
Played 2 rounds @Negril Hills, no tee time necessary, the golf course was in pretty good condition lots of hills, make sure you bring balls $15.00 for 3, also bring tees $4.00 for 5 tees all short, rented bag anywhere from $18- $40, both rounds only 4 people only on the course. Played both rounds early beat the heat, caddy a big plus, enjoy.