Best Caribbean Vacation Packages & Travel Deals

Cruise.com via ShermansCruise offers a Royal Caribbean 4-Night Bahamas Cruise for Two, with prices starting from $458. (On the ShermansCruise landing page scroll down and click "Book Now" next to the November 26 sailing date.) That's tied with our mention from two weeks ago as the lowest price we could find by $120, and the best price we've seen for a 4-night cruise on Royal Caribbean since the week of Black Friday. This roundtrip cruise aboard the Mariner of the Seas departs on November 26 from Miami, FL. Additional fees may apply. Book this travel deal by October 31.

Cruises.com via ShermansCruise offers a Carnival Cruise 5-Night Bahamas Cruise for Two with prices starting at $588. (On the ShermansCruise landing page, scroll down and click "Book Now" next to the September 24 sailing date.) That's the lowest price we could find by $20. This roundtrip cruise aboard the Carnival Elation departs from Jacksonville, FL, on September 24. Book this travel deal by May 31.

CruisesOnly offers a Norwegian Cruise Line 4-Night Cuba Cruise for Two bundled with a open bar with prices starting from $698, as provided by ShermansTravel. (It's the top offer on the landing page.) That's $100 below our mention from three weeks ago and the lowest price we could find for such a cruise today by $20. This roundtrip cruise aboard the Norwegian Sky departs from Miami, FL, on June 4 and includes stops in Great Stirrup Cay, Bahamas and an overnight stay in Havana, Cuba. Additional fees may apply. Book this travel deal by June 3.

Trivago discounts select 3- to 5-Star Hotel Stays in Cancun, Mexico, with prices starting from $26 per night, as provided by Dunhill Travel. (We found this rate for a 1-night stay on July 15.) That's the lowest nightly rate for select stays by at least $4. Additional fees and taxes apply. Book this travel deal by May 29.

Cruise.com via ShermansCruise offers a Carnival Cruise 3-Night Bahamas Cruise for Two, with prices starting from $428. (On the ShermansCruise landing page, scroll down and click "Book Now" next to the October 29 sailing date.) That's the lowest price we could find for such a cruise by $51. This roundtrip cruise aboard the Carnival Victory departs from Miami, FL, on October 29. Book this travel deal by September 30.

BookIt offers 5-Night Stays for Two at the All-Inclusive Royal Playa del Carmen Spa & Resort in Playa del Carmen, Mexico, with prices starting at $1,652.80 via coupon code "RESORT50", as provided by ShermansTravel. (It's the top offer on the page; we found this rate on October 7.) At $331 per night, that's the lowest nightly rate we could find by $50. This 4-star resort has an Expedia rating of 92% based on 3,861 reviews. Book this travel deal by May 31 for travel from August 12 through November 18.

CheapCaribbean via ShermansTravel offers InterContinental San Juan 4-Night Flight and Hotel Vacation for two in San Juan, Puerto Rico, with prices starting at $1,081.98. This price is based on departure on June 3 from Fort Lauderdale, FL, (FLL) with arrival in San Juan, Puerto Rico (SJU); other departure cities are available at an additional cost. That's the lowest price we could find by $35. This 4-star hotel has an Expedia rating of 86% based on 2,051 reviews. Book this travel deal by December 2 for travel from May 20 through December 16.

Cruise.com offers a Celebrity Cruises 4-Night Bahamas Cruise for Two with prices starting at $598, as seen on Travelzoo. (It's the fourth offer on the landing page; we found lower prices during booking.) That's the lowest price we could find for such a cruise by $40. This roundtrip cruise aboard the Celebrity Infinity departs from Fort Lauderdale, FL, on October 28 with stops in Key West, FL, and Nassau, Bahamas. Additional fees may apply. Book this travel deal by May 31.

BookIt via Dunhill Travel offers 5-Night Stays for Two at the Hilton Puerto Vallarta in Puerto Vallarta, Mexico, with prices starting at $1,040 via coupon code "RESORT50". (We found this rate on October 7.) At $208 per night, that's the lowest price we could find today by $220. This 4-star hotel has an Expedia rating of 80% based on 329 reviews. Book this travel deal by July 17 for stays from May 27 through December 17.

CheapCaribbean via ShermansTravel offers an All-Inclusive Dreams Puerto Aventuras Resort 4-Night Flight and Hotel Vacation for Two in Riviera Maya, Mexico, bundled with $200 Resort Credit with prices starting from $1,014.06. (It's the third offer in the right sidebar of the landing page.) Assuming you use the credit, that's the lowest price we could find by $223. This price is based on departure on May 6 from Fort Lauderdale, FL, (FLL) with arrival in Cancun, Mexico, (CUN). This 4-star Puerto Aventuras hotel has an Expedia rating of 81% based on 707 reviews and received the TripAdvisor Certificate of Excellence. Book this travel deal by June 30 for stays from April 30 through June 30.

CheapCaribbean via ShermansTravel offers an All-Inclusive Melia Nassau Beach Resort 3-Night Flight and Hotel Package for Two in Nassau, the Bahamas, with prices starting at $1,615.48. That's the lowest price we could find for this package by $83. This price is based on departure from Fort Lauderdale, FL, (FLL) with arrival in Nassau, Bahamas, (NAS) on June 10; other departure cities are available for an additional cost. This 4-star hotel has an Expedia rating of 67% based on 1,698 reviews. Book this travel deal by August 2 for travel from April 14 through August 19.

CheapCaribbean via ShermansTravel offers All-Inclusive Riu Palace Paradise Island 3-Night Flight and Hotel Vacation for two in Paradise Island, Bahamas, bundled with $710 in Resort Credit with prices starting at $1,546.82. This price is based on departure on August 21 from Fort Lauderdale, FL, (FLL) with arrival in Nassau, Bahamas (NAS); other departure cities are available at an additional cost. That's the lowest price we could find by $48. This 4-star hotel has an Expedia rating of 77% based on 3,730 reviews. Book this travel deal by December 4 for travel from July 1 through December 23.

BookIt via ShermansTravel offers a 5-Night Stay for Two at the All-Inclusive Pueblo Bonito Los Cabos Blanco Resort in Cabo San Lucas, Mexico, with prices starting at $2,134.14 via coupon code "RESORT50". (It's the top offer on the page; we found this rate on September 2.) At $427 per night, that's the lowest current rate we could find by $53. Additional fees may apply. This 4-star hotel has an Expedia rating of 82% based on 1,164 reviews. Book this travel deal by May 31 for stays from August 12 through October 29.

Riu Hotels & Resorts via Dunhill Travel offers Riu Santa Fe All-Inclusive 5-Night Flight and Hotel Vacation for two in Cabo San Lucas, Mexico, with prices starting at $1,069.19. This price is based on departure on June 17 from Los Angeles, CA (LAX), with arrival in San Jose del Cabo, Mexico (SJD); other departure cities are available at an additional cost. That's the lowest price we could find by $176. This 3-star hotel has an Expedia rating of 78% based on 6,111 reviews. Book this travel deal by May 26.