Best Caribbean Vacation Packages & Travel Deals

Cruise.com via ShermansCruise offers a Carnival Cruise 7-Night Eastern Caribbean Cruise for Two with prices starting at $778. (On the ShermansCruise landing page, scroll to the bottom and click "Book Now" next to the December 9 sailing date.) That's the lowest price we could find for such a cruise in December by $20. This roundtrip cruise aboard the Carnival Fascination departs from San Juan, Puerto Rico, on December 9. Book this deal by September 30.

Cruise.com via ShermansCruise offers a Carnival Cruise 5-Night Bahamas Cruise for Two with prices starting at $578. (On the landing page, scroll down and click "Book Now" next to the October 27 sailing date.) That's the lowest price we could find by $10. This roundtrip cruise aboard the Carnival Sensation departs from Miami, FL, on October 27. Book this travel deal by September 30.

Vacations to Go offers a Carnival Cruise 4-Night Mexico Cruise for Two, with prices starting from $368. That's the lowest price we could find by $20. This roundtrip cruise aboard the Carnival Victory departs from Miami, FL, on October 22. Book this travel deal by October 21.

Cruise.com via ShermansCruise offers a Royal Caribbean 4-Night Eastern Caribbean Cruise for Two, in an Oceanview Cabin, with prices starting at $511. (On the landing page, scroll to the bottom and click "Book Now" next to the January 9, 2019, sailing date.) That's the lowest price we could find for such a cruise by $85. This 1-way cruise aboard the Jewel of the Seas departs from San Juan, Puerto Rico, on January 9, 2019, with debarkation in Miami, FL. Book this travel deal by October 31.

BookIt offers a 5-Night Stays for two at the All-Inclusive Ventus at Marina El Cid Spa and Beach Resort in Riviera Maya, Mexico, bundled with $600 Resort Credit, with prices starting at $961.20 via coupon code "RESORT50", as provided by ShermansTravel. (It's the top offer on the page; we found this rate on November 1.) At $192 per night, that's the lowest current rate we could find for this stay by $331. This 4-star hotel opened in November 2017. Book this travel deal by September 24 for stays through November 9.

BookIt via ShermansTravel offers a 5-Night Stay for Two at the All-Inclusive The Grand at Moon Palace in Cancun, Mexico, bundled with up to $2,500 Resort Credit, with prices starting from $1,957 via coupon code "RESORT50". (It's the top offer on the page; we found this rate on December 9.) At $391 per night, that's the lowest price we could find by $50. Additional fees and taxes may apply. This 4-star hotel has an Expedia rating of 84% based on 180 reviews. Book this travel deal by September 24.

Bookit offers 5-Night Stays for Two at the All-Inclusive Secrets St. James Montego Bay, in Montego Bay, Jamaica, with prices starting from $1,993.32, as provided by Dunhill Travel. (It's the first offer on the landing page; we found this rate on August 5.) That's the lowest price we could find by $20. This 5-star resort has an Expedia rating of 86% based on 1,004 reviews. Book this travel deal by December 17 for stays from June 30 through December 17.

BookIt offers a 5-Night Stay for Two at the All-Inclusive Melia Cozumel Golf Resort in Cozumel, Mexico, with prices starting at $705 via coupon code "RESORT50", as provided by Dunhill Travel. (It's the top offer on the page; we found this rate on October 7.) At $141 per night, that's the lowest current rate we could find for this stay by $50. This 3-star hotel has an Expedia rating of 80% based on 1,264. Book this travel deal by December 17 for stays from June 18 through December 22.