Best Vacation Packages & Travel Deals to Caribbean

CheapCaribbean offers a Conrad San Juan Condado Plaza 3-Night Flight and Hotel Package for Two in San Juan, Puerto Rico, with prices starting at $726.52, as seen on Travelzoo. (Click on the top photo to book this deal.) That's $25 under our April mention and the lowest current rate we could find for this package by $137. This price is based on departure from Fort Lauderdale, FL, (FLL) with arrival in San Juan, Puerto Rico, (SJU) on July 23; other departing cities are available for an additional cost. Some dates may be excluded and additional fees may apply. Book this travel deal by May 28 for travel May 27 through August 31.

American Express Travel offers an All-Inclusive Now Jade Riviera Cancun 3-Night Flight and Hotel Package for Two in Riviera Maya, Mexico, bundled with a $200 resort credit with prices starting at $1,712.76, as provided by ShermansTravel. (Click on "check availability" next to "Now Jade Riviera" and use the right drop down menus on the resulting page to book this deal.) That's the lowest current rate we could find for this vacation by $319. This price is based on departure from Miami, FL, (MIA) with arrival in Cancun, Mexico, (CUN) on July 14; other departing cities are available for an additional cost. Some dates may be excluded and additional fees may apply. Book this travel deal by May 31 for travel through December 22.

BookIt offers 3-night stays for 2 at the All-Inclusive Hotel Riu Tequila in Playa del Carmen, Mexico, with prices starting at $516, as provided by Dunhill Travel. (Click on "Check Rates" and "Try Our Lowest Price Calendar" to find these rates.) That's the lowest current rate we could find for a 3-night, all-inclusive stay for two at this property by $4. Some dates may be excluded and additional fees may apply. Book this travel deal by May 24 for stays through November 30.

Of note, BookIt offers stays in other hotels in Riviera Maya with prices starting at $36 per person / per night. Scroll down to see them all.

CheapCaribbean offers a 4-night stay for 2 in a Superior Room at the All-Inclusive Lifestyle Tropical Beach Resort & Spa in Puerto Plata, Dominican Republic, with prices starting at $192, as provided by Dunhill Travel. (Click on the top photo to book this deal.) That ties our March mention as the second-lowest rate we've seen for stays at this property. It's also a current low by $208. A 4-night minimum stay is required. Taxes and fees are additional, and blackout dates may apply. Book this travel deal by May 27 for stays through December 23.

Virgin America offers select 1-way fares with prices starting at $58.90, as seen on Travelzoo. That's the lowest current base fare we could find for select flights by $10. This price is valid on flights from San Francisco, CA, (SFO) to San Diego, CA, (SAN) departing on June 11; prices vary depending on the travel cities and dates chosen. A 14-day advance purchase may be required and blackout dates may apply. Book this travel deal by May 29 for travel June 1 through November 20. Other notable routes:

• Los Angeles (LAX) to San Jose (SJC) from $58.90
• San Francisco (SFO) to Los Angeles (LAX) from $67.90 $61.90
• Seattle (SEA) to Los Angeles (LAX) from $98.90
• see all available Virgin America fares

Club Med takes 40% off select all-inclusive hotels in the U.S., Caribbean, and Mexico, as provided by Dunhill Travel. (Discount is shown at checkout.) That's the first such sale we've seen from Club Med this year. Additional fees and restrictions may apply. Discounted properties include Cancun Yucatan, Sandpiper Bay, Buccaneer's Creek, and more. Book this travel deal by May 22 for travel June 1 through October 26.

BookIt offers 3-night stays for 2 at the All-Inclusive Hotel Riu Palace in Riviera Maya, Mexico, bundled with in-room WiFi and a $35 spa credit with prices starting at $894, as seen on Travelzoo. That's the lowest current rate we could find for an all-inclusive, 3-night stay for two at this property by $41. Some dates may be excluded and additional fees may apply. Book this travel deal by May 24 for stays through November 30.

Of note, BookIt offers stays in other hotels in Riviera Maya with prices starting at $36 per person / per night. Scroll down to see them all.

Cruises Only offers a Carnival Cruise 4-Night Bahamas Cruise for Two bundled with a $25 onboard credit with prices starting at $338. That's the second-lowest rate we've seen for a 4-night Bahamas cruise from Carnival. Assuming you use the credit, it's also the lowest current rate we could find for this cruise by $25. This roundtrip cruise departs from Port Canaveral, FL, on November 10 with stops in Freeport and Nassau, Bahamas. Additional taxes and fees may apply. This travel deals ends May 23.

Virgin Vacations offers a Dublin City Inn 6-Night Flight and Hotel Package for Two in Dublin, Ireland, with prices starting at $1,698 via coupon code "VNC05DH13B", as provided by Dunhill Travel. (It's the top offer on the page; enter coupon during final checkout page.) That's the lowest current rate we could find for similar packages by $600. This price is based on departure from New York, NY, (JFK) with arrival in Dublin, Ireland, (DUB) on October 21; other departing cities are available for an additional cost. This deal includes roundtrip airfare, 6-night hotel stay in Dublin, fuel surcharges, and more. Some dates may be excluded. This travel deal ends May 22.

ShermansTravel offers American Airlines roundtrip flights to Mexico from select cities in the U.S. for as low as $277.38. (Click on "AmericanAirlines.com" in the main paragraph to see this sale; all taxes are included.) This price is valid on flights departing from Miami, FL, (MIA) to Cancun, Mexico, (CUN) on September 15 with return on September 24; prices vary depending on the travel cities and dates chosen. That's $18 under our April mention and the lowest current base rate we could find for select routes by $7. Book by May 29 for travel August 14 through December 7. Other notable deals:

• Dallas (DFW) to Monterrey (MTY) from $320.89
• Washington, D.C. (IAD) to Los Cabos (SJD) from $364.02
• Chicago (ORD) to Puebla (PBC) from $431.51
• see all available American Airlines fares to Mexico

Ocean by H10 Hotels offers stays for 2 at the Ocean Coral & Turquesa in Riviera Maya, Mexico, bundled with complimentary airport transfers with prices starting at $179 per night, as provided by ShermansTravel. (Click on "Choose This Offer" and select "Ocean Coral & Turquesa" from the drop-down menu to book.) That's the lowest current rate we could find for stays for two at this property by $20. Blackout dates and additional fees may apply. Book this travel deal by June 15 for travel through June 27.

Travelzoo offers 3-night stay for 2 at the Costa Baja Resort and Spa in La Paz, Mexico, with prices starting at $349. That's $226 less than the lowest rate we could find for a 3-night stay at this property. (6-night stays are available starting at $698. Room upgrades are also available for an additional cost.) Blackout dates and additional taxes and fees may apply. Book this travel deal by May 25 for travel through August 31.

Royal Caribbean offers a Royal Caribbean 3-Night Bahamas Cruise for Two with prices starting at $818, as seen on Travelzoo. That's the lowest current rate we could find for this cruise by $40. This roundtrip cruise departs from Port Canaveral, FL, on June 14 and includes stops in Nassau and CocoCay, Bahamas. Some restrictions may apply; fees, government taxes, and fuel supplements are additional. This travel deal ends May 31.