18 deals from our U.S. site*
* Taxes and fees may be additional.
Source: CheapCaribbean.com

Spend three nights at the Condado Plaza Hilton and receive an upgrade to an ocean view room.

Select departures May 3-6; Aug. 24 - Oct. 31
Source: Sheraton Old San Juan Hotel & Casino

Travel to the Sheraton Old San Juan Hotel & Casino which is situated in the heart of historic and romantic old San Juan.

Sundays-Thursdays May 4 - July 31; +$30 weekends
Source: Sheraton Puerto Rico Hotel & Casino

The Sheraton Puerto Rico Hotel & Casino features Puerto Rico's largest casino and four onsite restaurants

Sundays-Thursdays through Sept. 30
Source: Rincon Beach Resort

This deal is valid any day of the week and includes a one-hour kayak rental.

Through May
Source: Horned Dorset Primavera

This 4-star property is beachfront in Rincon, one of the world's premier surfing destinations.

Sundays-Thursdays May 1 - June 30
Source: Turtle Bay Inn

This deal is at an eco-friendly property and includes continental breakfast and parking.

Weekdays through May; +$20 weekends
Source: Parador Villas del Mar Hau

This hotel's rooms overlook the blue waters of the property's private beach.

Through April 9
Source: Villa Montana Beach Resort

Villas at this beachfront resort boast fully-equipped kitchens, dining areas, living areas and more.

Sundays-Thursdays through June; +$33 weekends
Source: Aquatica Dive, Surf & SUP's

Explore Aguadilla with the number two ranked attraction on TripAdvisor.

Through May
Source: Hilton Ponce Golf & Casino Resort

This beachront resort is the only 4-star property in Ponce.

April 1 - June 28
Source: Holiday Inn Mayaguez & El Tropical Casino

This hotel is ideally located in the center of Puerto del Sol's largest city.

Weekdays through April; +$7 weekends
Depart Nov. 8; +$30-$100 Oct. 25; Nov. 22; Dec. 6
Depart Nov. 1, 15 ,29; Dec. 13; +$100 oceanview
Select departures May 2-10; Aug. 24 - Oct. 31
Cheap Roundtrip Fares to San Juan from:
(Per person, including taxes and fees. Click a price to verify availability now.)
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Andrew Young — Travel, Entertainment and Local Deal Expert
Andrew Young
Deal Expert, New York
Summer is coming. Our thoughts turn to beaches, grilling meats and summer vacation. More