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San Juan February School BreakWhen I went from being a father of two to a father of three I got many “What were you thinking?” comments from friends, other parents, supermarket cashiers – virtually anyone who felt comfortable observing that my wife and I had exceeded some maximum. And you know who else I still hear it from? Hotel booking engines, which respond to my request for a single room accommodating two adults and three children with “exceeds max children” or some similar admonishment.

From the moment I began traveling with my party of five, my strategy has been to check the rate on a standard double room that takes two adults and two kids, and from there, grill reservationists about whether the room has a sofa bed or will accommodate a rollaway. I also ask if  there’s a charge for the extra bed and/or an extra occupancy fee for my additional child. Much of the time I’m pleasantly surprised by the answer. And then there are those times like the other night when I called the Caribe Hilton in San Juan to see if the $269 a night room I found for February 20-24 allowed a rollaway. Nope.


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The Hilton reservationist also couldn’t guarantee a rollaway would be available even if one was permitted. However, she pointed out, I could have the two-bedroom presidential suite for $2,199 a night. Not this time, I said. If you do have the standard two kids, $269 a night isn’t bad, nor are other rates available through Hilton’s 4th Night Free discount – though you can’t always get the free night on the rooms with the lowest rates. The chain’s Any Weekend, Anywhere special affords a bit more flexibility and is worth checking out for a potential 20-50 percent discount if you book before the end of January.


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My motivation for using the Caribe Hilton for this booking exercise was that I had fond memories of staying  there as a child – before it had a Morton’s steakhouse or Starbucks on site – and if you have two kids, the hotel is still a worthwhile base for a San Juan vacation. But if you have three children and would rather avoid the presidential suite during your kids’ February break, two other properties are worth investigating.

For my sample dates of February 20-24, Embassy Suites Hotel & Casino in San Juan has a two-room suite available for $159 a night – part of the aforementioned Any Weekend, Anywhere deal, since Hilton and Embassy Suites are part of the same happy hotel family. The hotel is less than a mile from San Juan Luis Munoz Marin International Airport (SJU) and a free cooked-to-order breakfast is included every morning of your stay.

Another option is the Sheraton Puerto Rico Hotel & Casino, as of this writing $164 a night when booked through Expedia for the same four nights in February. The “superior bay view” room has two double beds and a Sheraton reservationist verified that a rollaway bed, at a rate of $25 per night, would be available to accommodate my third child who ordinarily exceeds the max.

Use our Travel Search price comparison tool to find the lowest rates and travel deals on hotels, flights, vacation packages, and more. For general trip-planning information, see our San Juan Travel Guide.

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