Puerto Rico Vacations

Fall in love with Puerto Rico and the myriad unique and thrilling experiences it offers. Discover centuries-old fortresses; stroll along quaint cobblestone streets that wind through the vibrant colonial enclave of Old San Juan; catch some sun or ride the waves on some of the world’s best beaches; explore the only rainforest in embark on a gastronomic adventure that showcases the best of local flavor and global talent.

3 nights with round-trip air from $439


Sheraton Puerto Rico Hotel & Casino

Find non-stop excitement, with the largest Casino on the island, 4 restaurants/3 bars, 24 hour fitness and a full service spa.

3 nights with air from $439


Gran Meliá Golf Resort Puerto Rico

With an idyllic location on Puerto Rico's northeastern coast in Coco Beach, this 486-room resort offers privacy and exclusivity.

3 nights with air from $455


Wyndham Grand Rio Mar Beach Resort & Spa

Situated on 500 acres of beachfront property, this non-smoking resort offers breathtaking views, outstanding snorkeling and countless entertainment options.

3 nights with air from $475


Caribe Hilton San Juan

Set within lush gardens near historic Old San Juan, this resort features breathtaking views of the Atlantic Ocean.

3 nights with air from $565


San Juan Marriott

This full-service, four-diamond luxury resort along Condado Beach in San Juan offers the perfect balance of adventure and relaxation.

3 nights with air from $565


The Ritz-Carlton, San Juan

Ideally located on eight acres of prime beachfront property in Isla Verde tourist area, The Ritz-Carlton, San Juan offers 416 air-conditioned guest rooms each filled with a myriad of in-room amenities.

3 nights with air from $845


The St. Regis Bahia Beach Resort

Set on a former coconut plantation and native maritime forest, this resort introduces an unrivaled dimension of luxury and bespoke hospitality.

3 nights with air from $915


W Retreat & Spa, Vieques Island

This gorgeous resort nestled on the pristine island of Vieques offers luxurious indulgences.

3 nights with air from $1,319

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Rates are based on roundtrip air travel to/from Boston (BOS) to Puerto Rico and are per person, based on double occupancy. Advertised vacation rate(s) valid for departure 8/22/17.
Caribbean – Exclusive $100 OFF: Valid on new bookings made 3/27 – 5/7/17 for travel 3/27 – 12/16/17 at participating hotels and resorts. Roundtrip air and 3-night minimum stay required. Savings is per booking and taken at time of booking.
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.]