Agree with reworking the kitchen, perhaps with an island and seating around it.

I'm not sure what table I would use may go against the old fashion style and do the island and smaller or contemporary dinning. The living now needs ideas...lol...
Accepted about the bedroom layout as well.

You might consider a larger or double window in the first bedroom and having only one large window in each of the corner rooms. This will allow more wall space and give you greater options for furniture placement. We recently built our house and I kick myself all the time for not installing larger windows in the secondary bedrooms.

Also, is there a designated front entrance?

Yes Darren M, agreed about the larger window in the smaller bedrooms. The front entrance is located between the kitchen bar and the bedroom wall. Will have a canopy like extended front porch to enter....with some pillars

Unless you use air conditioning all the time in Barbados or the house is in the middle of a city no way would I give up the cross ventilation in the two bedrooms for ease of furniture purchase/placement. I would want as much island breeze and scent as I could get. No question furniture is an issue but you can figure out something besides getting rid of the window. Use underbed storage, max out use of the closet, build In something if you have to.