I stayed at this hotel a couple of weeks ago for a long weekend. We traveled with a group of friends for a wedding and were spread out among three hotels, with the other two properties being La Concha and the Vanderbilt. La Concha is in the same price point as the Caribe and is much nicer. We paid with points at 50,000 a night. As others have mentioned, if you have to stay here this is the way to go. The $400+ rates are outrageous. First for the positive aspects of the stay, we found the diamond treatment to be excellent. We were proactively upgraded at check-in to a junior suite in the ocean front tower, we also enjoyed having options for breakfast. They let you chose a free continental buffet, a second full buffet for $11 each, or if you don't want to go to breakfast you can have a $20 credit for two for food or drinks in the resort. The room had a nice ocean view in the beach tower and it was quiet because we were at the end of the hall in the junior suite. They are also very responsive to the texting and in app concierge. We also found the food on property to be of high quality. They have a great team at the lobby bar.
For the downsides, the property felt more like a convention hotel than a beach property. While the lobby bar was nice, the check-in area is basically a large, open, space with white walls and not a lot of character for convention goers to hang out. It is constantly busy, like an airport terminal. They also do not allow uber into the main driveway up to the property, you have to walk down the side of the hotel to a pick up area. This is the only hotel in San Juan that does this. Taxis line-up in the driveway at the lobby, and they won't allow Uber to drive there. The security guards are very rude to Uber drivers. In one case, he cursed out our uber driver who was just doing his job and picking us up in the designated pick up zone. He stopped for 20 seconds so we could put our bags in the trunk, and this was what set the security guard off. This left a very bad taste for us. Also, they will close the entire outside of the hotel in nice weather for mild winds. This includes the beach, pathways, pool decks, pool areas, outside bar, etc. This happened everyday during our stay. They said it was for "high winds", but 20mph winds are common on the water and it was just such nice weather with beautiful skies. No other resort did this, as we could see from our balcony. At least we were able to go see our friends at La Concha and enjoy that pool (which never closed) or go to the public beach next door, which was calm, nice, and quiet. As you can imagine, the lobby was full of frustrated people who were mainly there for the beach and the pools to find locked doors and security guards. They wouldn't even let anyone take a walk on the paths by the water to enjoy the view. As a result of these downsides, we would never return or recommend the hotel to anyone for a vacation. If I was able to do it again, we would have just paid and stayed at La Concha or the Vanderbilt despite the great points redemption.