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 EXCLUSIVE - $100 OFF per booking

  • Book by 11/02/25 for travel through 06/30/26
  • San Juan Marriott Resort & Stellaris Casino
    San Juan Marriott Resort & Stellaris Casino
    San Juan, Puerto Rico Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    Soak up the sun in style at this full-service luxury resort along Condado Beach in San Juan which offers the perfect balance of adventure and relaxation.

    Book Now

Caribbean $100 OFF per booking Offer: Valid on new bookings made 09/08/2025 – 11/02/2025 for select travel 09/08/2025 – 06/30/2026. Minimum 3-night hotel accommodations at participating property and roundtrip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. 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.]