The Condado Plaza Hilton in San Juan, Puerto Rico, offers summer stays starting from $139 per night, as provided by ShermansTravel. That's a savings of at least $140 compared to booking at other times of the year. This 4-star hotel has an Expedia rating of 88% based on 3,116 reviews. Book this travel deal by December 15 for stays from June 1, 2016 through October 31, 2016. The stays:

• Stays from August 1, 2016 through September 29, 2016 from $139 per night
• Stays from June 1, 2016 through July 31, 2016 from $149 per night
• Stays from September 30, 2016 through October 31, 2016 from $159 per night