Fleckre, we stayed one week in Simpson Bay ( dutch side ) one week in Orient Beach, and one week in Grand Case - vbro or homeaway for our 3 different trips. Grand Case is the place to be, you can find high end restaurants, but there are lolos at the north end where you can eat at a picnic table, and picnic table fare and a pizza place at the sound end of town as well. While the street is dark, and there is no sidewalk, just watch where you are walking , we walked to dinner and back each night, no problems. If you want to go to Orient for a day, it is a very short trip. Orient Beach got very quiet at night, and very few dining options on the beach, though there are more in the Orient village area. If you rent a VBRO or homeaway in Grand Case - check on the parking - not sure if it matters as much in June, but in the busy season it is nice to have dedicated parking. You won't need a car if you just stayed in Grand Case, but we liked taking day trips to other nearby beaches.