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 Vacation Sale
Hotel discounts, FREE nights, resort credits and more

  • Book by 12/6/20 for select travel through 1/6/21
Vacations Include: Round-trip flights, hotel accommodations, taxes and more
  • 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 San Juan Marriott Resort & Stellaris Casino. This full-service, four-diamond luxury resort along Condado Beach in San Juan offers the perfect balance of adventure and relaxation.

    Book Now
  • Hyatt Regency Grand Reserve Puerto Rico
    Hyatt Regency Grand Reserve Puerto Rico
    Rio Grande - STB 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.

    Explore tropical island living with a contemporary twist at this upscale resort with two championship golf courses.

    Book Now
Caribbean Winter Vacation Sale: Valid on new bookings made 11/2/20-12/6/20 for select travel 11/2/20-1/6/21. Minimum 3-night hotel accommodations at participating property and roundtrip airfare required. Savings is per booking, taken at time of booking and reflected in rates shown.
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]