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With its own beach and large swatches of tropical gardens, the Caribe Hilton is still one of San Juan's finest properties in a city full of them. The infinity pool (plus two other pools), wide variety of restaurants (from Morton’s to Quiznos) and picturesque Caribe Terrace bar and lounge, where the piña colada is said to have been born, are a large part of its appeal. The Caribe does have its challenges, however (and a 2014 renovation program suggests that staff is addressing them). First off there’s a wide gulf between the quality of the rooms in the old and new towers. In the former, you’re likely to experience slow elevators, cranky plumbing and dated décor. In the new, well, everything is newer, spiffier and up to Hilton’s usual standards (so ask to change towers if you’re not pleased with your digs). The Caribe’s other problem is less fixable and that’s its location, a neighborhood that is a nowhere man's land after dark, with very little commerce in the area anytime. Sure you can take a cab back home from Condado or Old San Juan after an evening meal, but all those cab fares do start to add up. Still, the views from the hotel are great, as is that private beach and because there are so many rooms to fill here, the Caribe often discounts deeply (do a thorough web search before booking).