My advice...go island time.
Driving on the left is no big deal. Different yes, but not a vacation ruiner (?) by any means. Remember, you are on vacation. No where to be, no meeting to be at, no problem mon (with all due respect). If you get there early, they won't be open anyway and in no hurry to serve and quite frankly that is why you are going to VI in the first place. If you wanted service go to Vegas or Disney World. If you want to chill, revive the soul and get to know your mate or friends better than you do already go to he VI.
When you come to the switchback and can't see the road in front of you, honk the horn to let someone know you are there (not like you want to get them moving at a light when back home). The limit is 20 MPH and at times you will think "that's just suicidal!" but again, you are not trying to catch a train so 'go with the flow'.
Bottom line, don't worry. Enjoy it, you will be back home on the RH side soon enough and wishing you were driving on the 'wrong' side again.

2 door Jeep Wrangler has very limited amount of luggage space.
There are plenty of luggage space in the 4 door Wrangler or Liberty. (unless you are bringing your whole closet.)
For 4 adults, everyone will be more comfortable in the Wrangler or Liberty -
With 2 door, people will have to climb in and sometime this is not the easiest thing to do.
4 door Wrangler or Liberty, everyone can have their own door.
Hope this helps!!!

With four people and luggage/and beach equipment you'll definitely want to go with the 4 door Wrangler. The Liberty is too small and the 2 door Wrangler is waaaaay too small.

Disregard my earlier reply tennisfan84. Not sure how it got on this topic but I must chalk it up to User Error.
Unless you plan on making numerous trips or packing the luggage on top of the passengers I suggest the Liberty. Both the 2 &4 foor Wrangler have about the same practical space.

With 4 people, I can not recommend a jeep, 2 or 4 door.
A 2 door is an absolute no. There is no room at all and it is a pain in the butt to get in that back seat,
A 4 door will give more passenger room but not any more storage for bags.

we love the Jeeps but gave up on renting them. Just too small for beach chairs, beach bag, and a cooler.

We have rented the Liberty with 4 adults and luggage to match. It was a tight fit with the luggage but it made it and we had plenty of room for us and our beach gear each day

Thanks everyone for the advice. We ended up renting a Suzuki Grand Vitara-4 Door.... Dependable was sold out of the 4 door wranglers.
Hope it will be big enough for the 4 of us! We should have rented back in April...the prices have gone up considerably for the time we will be there (7/1-7/11)

You will be very happy with the Grand Vitara. Plenty of room for passengers and luggage.