What is the easiest & reliable car to keep maintained if I’m not doing it myself?
It depends what country are you staying in. In the Philippines, our Isuzu Crosswind is easy to maintain because the mechanic guy and shop is just near the place I stayed. It is reliable because we’ve been using it for years. It actually depends how you use your car and the availability of the person who will maintain its good condition. 
Whatever you get, do not buy anything European. Easy and reliable do not apply to any European brand.
Early '90s GM with a pushrod engine. Quad Fours can be reliable as well, if they have been properly maintained. Given the unknown factor, you should stick with the pushrod motors. GM cars of this era are simple and bulletproof, labor rates are low, anybody who calls themselves a mechanic have worked on them, and parts are cheap, easy to find, and easy to replace. Hondas and Toyotas are also reliable, but require routine timing belt changes. This job ranges from $400-1000 depending on the vehicle if you include a water pump and tensioner with the job. This maintenance requirement can be a deal-breaker for some, which is why I recommended older GMs first.
If you are not doing the work yourself, any car is easy to maintain. After all what is easier than some one else doing the work, while you lounge around the pool sipping cocktails.
I LIKE THE BIT ABOUT THE COCKTAILS! I currently own a '99 Honda CRV. Love the car. My (around the corner) mechanic has the same year and model, so he knows what he’s doing. Repairs have been manageable and not too expensive. But every car has its lifespan, so I’m looking at the Element as a replacement. A test drive tells me it feels like my CRV. (Don’t like the new CRV styling). Appreciate everyone’s input. Please feel free to comment on this post.
Reliability and maintenance costs for the Element should be similar to the CRV.
A Toyota RAV-4 would also be a good choice as a replacement for the CRV.
Somewhere in the mid-2000’s Toyota changed (at least on some models) to timing chain instead of timing belt. My 2000 Camry had a belt; the 2004 Camry and 2007 Corolla did not. I don’t know about Honda (or other makers). I, too, prefer to pay the up-front cost for the chain and not have the every-several-years high-cost maintenance of the belt.
The easiest car to work on would be a street-legal dune buggy. There are no body panels to get in the way. There isn’t even a hood. If you can find one with a Honda Civic or Honda Accord engine, it should be as reliable as it is easy to work on.
Now if you have other concerns, like shielding yourself from the sun and weather, or you want amenities like heat and air conditioning, you will have to seek other options. However, based on the lack of criteria, I recommend you get a street-legal dune buggy and have a rebuilt Civic or Accord engine installed.