The Francis Bay house, if it is the one I am thinking of, the walk to the beach isn't bad at all. Is it Honeymoon Cottage? That is a great location. The drive to Cruz Bay would be via North Shore Road, which is all paved.
I found this rental agency to be very helpful. Tell them what you are looking for and they'll give you a list of options, they live on STJ -
http://www.villafish.com/I stayed above the house you mentioned, it is a good location for access to town.
We stayed here last trip. I didn't love the location or the way the pool was behind the house with no view (from the pool) but the house itself was very nice -
http://www.caneeltrailside.com/inside.htmlWe almost rented this house and I still have it on the list for a future trip. It is above your budget but it couldn't hurt to ask the agency for a discount -
http://www.cateredto.com/ebb-tide/#.UrMSeXIo7csCheck out Beit Hawa on this list -
http://www.cateredto.com/villas/#.UrMTa3Io7cvTerrahawk is also on that list. Above your price range but I have seen some nice discounts offered on that one and the property next door, Kallaloo, which is my absolute favorite location on the island.
I'll post more as I think of them.
