Puerto Rico Deals

Puerto Rico Vacation Packages

 
Sun, sea, sand and history - come experience it all! Puerto Rico's status as a US commonwealth means you can leave your passport at home, so there's no excuse to let the beauty of this Caribbean island pass you by.

Walk the colorful streets of Old San Juan and visit colonial fortresses, letting your imagination carry you on a journey into the past. Relax on miles of pristine tropical beach or get your feet wet with swimming, snorkeling, kayaking and some of the area's best surfing. Or, if you're the type to travel on your stomach, explore the amazing local cuisine and try some of Puerto Rico's famous rum.

Caribbean Winter & Spring Vacations
Exclusive $100 OFF per booking

  • $200 OFF stays of 7 nights or longer
  • $150 OFF stays of 5-6 nights
  • Book by 01/15/23 for travel through 06/30/23
  • Caribe Hilton
    Caribe Hilton
    San Juan, Puerto Rico Our 4-Star

    Resting on a beautiful peninsula, the iconic Caribe Hilton is a positively paradisiacal resort. Situated on 17 acres of tropical landscaping, the resort is ideally located just a short distance from historic Old San Juan and the vibrant Condado district.

    Book Now
  • Royal Sonesta San Juan
    Royal Sonesta San Juan
    San Juan, Puerto Rico Our 4-Star

    This upscale hotel is situated on a white-sand beach and features upscale guest rooms and suites overlooking palm-fringed Isla Verde Beach and the sparkling Atlantic.

    Book Now
Exclusive Caribbean up to $200 OFF per Booking Offer: Valid on new bookings made 11/21/22 – 01/15/23 for travel 11/21/22 – 06/30/23. Minimum 5-night hotel accommodations at participating property and roundtrip airfare required. Minimum 7-night stay required for $200 savings. Minimum 5-night stay required for $150 savings. Savings is per booking and taken at time of booking. This entire offer is based on availability and can be modified or closed out at any time. 
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]