St. James, Barbados—$2,454-$3,385/Night
Don’t let the “reasonable” price fool you – this luxury holiday villa is still in a class by itself. Located in the exclusive Royal Westmoreland resort, “The Westerings” – as its known by those who are so well off that their familiar enough with the place to give it a nickname – is nestled in lush gardens and tropical Barbados landscape. Views soak up the nearby golf course and vibrant blue waters of the Caribbean Sea. The custom built property includes a palm-fringed terrace, infinity pool and Jacuzzi hot tub. Five bedrooms offer luxury views with the master boasting private lounges and a spa-like ensuite bath. There’s a guest cottage to house further revelers, and guests can partake in air hockey and table football in the games room. A golf buggy gives guests a quick and easy way to boot around the resort, while a housekeeper, cook, and butler can be hired on at an extra charge if you’re feeling particularly “Downton Abbey”.