So you want to take a surfing trip in the Caribbean .... Puerto Rico is a great choice. The surfing Season in Rincon, Puerto Rico is pretty much October to March ... although, swells can come thru anytime during the year! A lot of information on planning your surfing vacation in Puerto Rico can be found on our sister site SurfWestPR.com
As for where to rent for your Rincon surfing vacation, well, it really depends if you'd like to walk out your rental door and hit the same surf spot everyday without any driving -or- maybe you'd rather stay more economically and drive to all the different Rincon surf spots.
Here are our rentals that would allow you to walk out your rental door and hit the Rincon surf (depending on the swell)
Here are our rentals that are less than a couple miles from some great Rincon surf spots
Any of our rentals are a short, 10 minute-ish, drive to all these Rincon surf spots ..... with the exception of Ashley's Ocean View (close to Anasco, on the South end of Rincon) with a 15 minute drive to any of the spots previously mentioned.