Group Trip Suggestions
 

I'd like to do a long weekend trip to somewhere warm with a bunch of friends in January, probably about 8 people total. The lodging portion of the trip will be my treat, so it can't be anything too expensive. Its probably more economical to get a house or something like that than to pay for separate hotel rooms, but I'm open to suggestions. I'd like to go somewhere warm, relaxing, preferably a beach, that has places we can go out at night. Also, preferably convenient to get to, since we'd only be going for a few days (3-5, I think) and I dont want to spend the whole time traveling. Anyone have suggestions?

You'll probably have to go for 5 days, as you will loose travel days regardless of where you choose. Keep in mind January is oeakseason in Caribbean, so it's the most expensive time to go.

Fr cheaper destinations you might want to check out Cozumel, Costa Rica, and Dominican Republic.

we always stay in villas & it is less expensive, especially for a large group. more so if you're willing to do some cooking. off the top of my head easy to get to, economical villas is maya riviera coast. for some nightlife look near akumal. for more nightlife & duty free shopping near playa del carmen.
as blamona said it 'oeakseason' which translate to high season in regular life, meaning high prices & you need to book asap.
a very useful site to find houses & info on all to see/do in the area is locogringo.com

we always stay in villas & it is less expensive, especially for a large group. more so if you're willing to do some cooking. off the top of my head easy to get to, economical villas is maya riviera coast. for some nightlife look near akumal. for more nightlife & duty free shopping near playa del carmen.
as blamona said it 'oeakseason' which translate to high season in regular life, meaning high prices & you need to book asap.
a very useful site to find houses & info on all to see/do in the area is locogringo.com

sorry for the double post. got a screen that said error...

Thanks. I was originally thinking Mexico, and I've enjoyed the riviera maya area in the past, but lately I keep hearing that Mexico is becoming increasingly unsafe. I'm sure people will jump all over me for that, and say its only certain areas, not to do with tourists etc., but I'm not sure its worthwhile to chance it when I'm sure there are other places I could go where it wouldnt be an issue.

you are correct that the crime you refer to is only in certain areas - around 2000 miles away. there have been 2 major crimes in the area in the past few years. the american tv producer that murdered his wife at the hotel in cancun & a man from cozumel murdered his cruise ship employee girlfriend.

moving on. where are you traveling from?
grand cayman has lots of great villas but is a pricey island.
barbados is fabulous & is known for it's staffed beach houses - longer flight & a bit more expensive than maya riviera.
jamaica has good houses, normally with full staff - on the more reasonable side, but actually has some history of crime on tourists..
st. john in usvi has loads of villas & is pretty safe (there have been some robberies) - you fly to st. thomas then take ferry 45 mins to st. john.
overall, imho every caribbean destination is fairly safe unless you ignore all normal precautions (ie don't leave camera in full sight in open car) but no place is paradise/crime free.
maybe you could tell us a bit more about how you want to spend you time

Putting aside that I'm the worlds worst speller, my new iPad isn't helping much in that department either.

The 3 places I suggested are more affordable places, even once you're there. You don't want to get by in an economical place on an expensive island, cause you still have to eat and play!

I'll look into those places, blamona. Can you think of any particular accomodations that you can recommend?

Virginia, I am coming from the east coast of the US and it will be cold here in January, so mainly I just want to get a group of people together to get away somewhere warm. It will be my birthday, so I will probably want to go out and celebrate at least one night, but other than that I don't really want to do anything, other than relax. I'm leaning towards a villa partly because I think it will be cheaper, but I also like the idea of just sitting out on a terrace, reading and sipping cocktails. Does that help?