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.
 

EXCLUSIVE $100 OFF per booking

  • Minimum 3-night vacation packages
  • Book by 10/27/19 for travel through 6/28/20
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Caribe Hilton
    Caribe Hilton
    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.

    Set within lush gardens near historic Old San Juan, this resort features breathtaking views of the Atlantic Ocean.
    • Beach Standard With Balcony - King Bed
    • Exclusive $100 Off per booking

    3 nights with flight from $653+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
    See Details
  • Sheraton Puerto Rico Hotel & Casino
    Sheraton Puerto Rico Hotel & Casino
    Old San Juan 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.

    This remarkable hotel near historic Old San Juan overlooks the bay, affording splended views and a wealth of amenities.
    • Traditional Double/Double
    • Exclusive $100 Off per booking

    3 nights with flight from $837+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
    See Details
  • The St. Regis Bahia Beach Resort
    The St. Regis Bahia Beach Resort
    Rio Grande - STB Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Set on a former coconut plantation and native maritime forest, this resort introduces an unrivaled dimension of luxury and bespoke hospitality.
    • Garden View King Casa Caribe
    • Exclusive $100 Off per booking

    3 nights with flight from $992+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
    See Details
  • Dorado Beach, a Ritz-Carlton Reserve
    Dorado Beach, a Ritz-Carlton Reserve
    Carolina Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    This private retreat, once a plantation, features beautiful beachfront accommodations, three spectacular 18-hole golf courses and the historic Rockefeller Nature Trail.

    • East Beach Garden Reserve, Ocean Front Luxury King/King, 1st Level
    • Exclusive $100 Off per booking

    3 nights with flight from $2086+

    Newark, New Jersey (EWR) departures, valid for travel 12/02/19 - 12/05/19
    See Details
Caribbean - EXCLUSIVE $100 OFF per booking offer: Valid on new bookings at participating resorts made 8/26 - 10/27/19 for travel 8/26/19 - 6/28/20. Roundtrip airfare and minimum 3-night stay at a participating hotel or resort required. Discount is per booking, taken at time of booking and reflected in rates shown.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]