Just yesterday I booked a trip there for October. Only me and my wife though so it will be a very different trip. We've been there before so I can offer a bit of advice though.
For nightlife you'll either want to be in/near downtown Hamilton or at a location that gives you quick access to it by ferry, bus, or taxi. Cabs are pretty expensive around there and the bus system is pretty awesome so while you'll likely have a bunch of guys splitting rides, taking the bus around isn't a bad alternative. If you're planning on spending a lot of time at the beach, you probably won't want to stay in Hamilton. Most of the hotels there either don't have their own beach, so you take shuttles and even ferries to other beaches, or have private beaches that are still a golf cart away.
From what I've seen, houses for rent tend to be far away from most things so maybe look more into villas/cottages at hotels than a VRBO type...but maybe you get lucky.
The Fairmont Southampton has a really nice par 3 course that can be played in about 2 hours apparently, and Port Royal is one of the best courses you can play.
We're staying at Elbow Beach...the public beach is pretty popular and a pretty frequent stop for tourists but they have their own private beach as well. It was expensive (as is everything on the island) but they have some good specials going, 3rd night free, etc (we're going 6 nights). We are going much more for beach and relaxing than nightlife so being at a nice resort right on the beach was more important.
If you end up looking more into hotels, Grotto Bay is a good lower cost option. Good location, has an all inclusive plan if you choose to do it. We stayed there our first time around.
