Best Caribbean Vacation Packages & Travel Deals

CheapCaribbean offers an All-Inclusive Riu Santa Fe 4-Night Flight and Hotel Vacation for Two in Los Cabos, Mexico, with prices starting from $1,034.52, as provided by ShermansTravel. Plus, kids 12 and under stay and eat for free. That's the lowest price we could find for this package by $77 and the best deal we've seen for a 4-night flight and hotel vacation at this property. Book this travel deal by July 31 for travel from August 18 through October 26.

Virgin America via ShermansTravel offers select Virgin America Roundtrip Fares to San Francisco, CA, with prices starting from $96.40. (On the ShermansTravel landing page, click on "VirginAmerica.com" in the top paragraph to see this offer; although the landing page shows fares from $113, we found lower fares within.) That's tied with our mention from last week and the lowest price we could find for select routes today by at least $20. Book this travel deal by July 31.

All prices, dates, and booking details were valid at the time of publication.

Virgin America offers select 1-Way Cross Country Fares Nationwide with prices starting at $138.20, as seen on Travelzoo. That's the lowest price we could find for select routes by at least $9. A 21-day advance purchase is required. Book this travel deal by July 31 for travel from August 15 through November 15.

All prices, dates, and booking details were valid at the time of publication.

VacationsToGo offers a Carnival Cruises 4-Night Mexico Cruise for Two with prices starting from $498. That's tied with our mention from last week and the lowest price we could find now by $60. This roundtrip cruise aboard the Carnival Imagination departs on October 1. Additional fees and taxes may apply. Book this travel deal by July 31.

CheapCaribbean via ShermansTravel offers an All-Inclusive Grand Oasis Cancun 5-Night Flight and Hotel Package for Two in Cancun, Mexico, with prices starting at $1,353.60, via coupon code "OASIS50". (The coupon may apply automatically.) That's the lowest price we could find for this package by $42. Book this travel deal by August 31 for travel from August 17 through December 21.

CheapCaribbean offers a Condado Plaza Hilton 4-Night Flight and Hotel Package for two in San Juan, Puerto Rico, with prices starting from$954.40, as provided by ShermansTravel. That's the lowest price we could find for this 4-night San Juan vacation by $50. Book this travel deal by September 18 for travel from October 1 through December 21.

CheapCaribbean offers an All-Inclusive Sunscape Puerto Plata 5-Night Flight and Hotel Package for Two in Puerto Plata, Dominican Republic, bundled with a $100 Resort Credit, with prices starting at $1,079.52, as seen on ShermansTravel. Plus, two kids 12 & under can stay and eat for free. That's tied with our mention from two weeks ago and the lowest price we could find today by $73, excluding the extras. Book this travel deal by July 31 for travel from August 19 through December 22.

Playa Hotels & Resorts takes up to 50% off stays at All-Inclusive Hyatt Zilara Cancun in Cancun, Mexico, as provided by Dunhill Travel. Plus, bag $200 in Resort Credit for free. This 4-star resort has an Expedia rating of 96% based on 2,461 reviews. Book this travel deal by July 28 for stays through December 24.

Norwegian Cruise Line offers a Norwegian Cruise Line 3-Night Bahamas Cruise for two bundled with a complimentary open bar with prices starting from $658, as provided by ShermansTravel. (It's the first listing on the landing page.) That's the lowest price we could find for such a cruise in September by $100. This roundtrip cruise aboard the Norwegian Sky departs from Miami, FL, on September 8. Additional fees and taxes apply. Book this travel deal by July 31.

Vacations to Go offers a Carnival Cruise 5-Night Mexico Cruise for two, with prices starting at $658. That's the lowest price we could find for such a cruise in September by $20, although we saw it for $40 less two weeks ago. This roundtrip cruise aboard the Carnival Fantasy departs from Mobile, AL, on September 23. Book this travel deal by July 31.

Playa Hotels & Resorts takes up to 55% off stays at All-Inclusive Hyatt Ziva Los Cabos in San Jose del Cabo, Mexico, as provided by ShermansTravel. Plus, stay four nights or more and get the fourth night for free. This 4-star resort has an Expedia rating of 92% based on 1,162 reviews. Book this travel deal by July 31 for stays through October 31.

CheapCaribbean offers an All-Inclusive Iberostar Playa Mita 4-Night Flight and Hotel Package for Two in Riviera Nayarit, Mexico, with prices starting at $1,102.58, as provided by ShermansTravel. (It's the second offer on the sidebar on the right side of the landing page.) That's the lowest current rate we could find for this package by $172, although we saw it for $22 less last week. Book this travel deal by July 31 for travel from August 13 through October 31.

Vacations To Go offers a Carnival Cruise 4-Night Bahamas Cruise for Two bundled with $50 Onboard Credit, with prices starting at $558. Assuming you'll use the credit, that's the lowest price we could find by $50. Additional fees and taxes may apply. This roundtrip cruise aboard the Carnival Liberty departs from Port Canaveral, FL, on October 1. Book this travel deal by August 1.

BookIt offers 7-Night Stays for Two at the All-Inclusive Grand Sunset Princess All Suites Resort in Playa del Carmen, Mexico, in a Deluxe Junior Suite with Jacuzzi, with prices starting at $1,298.24 via coupon code "SAVE100", as provided by Dunhill Travel. (It's the top offer on the page; we found this rate on September 3.) At $181 per night, that's the lowest price we could find by $360. This 4-star hotel located in the Riviera Maya has an Expedia rating of 79% based on 2,231 reviews. Book this travel deal by July 28 for stay through December 19.

Travel Up via TripAdvisor offers stays at the Westin Resort and Spa Cancun in Cancun, Mexico, with prices starting from $107.10 per night as provided by ShermansTravel. (We found this price for a 4-night stay on August 22.) That's the lowest nightly rate we could find by $13. This 4-star resort has an Expedia rating of 82% based on 2,793 reviews. Book this travel deal by July 31 for stays through August.

BookIt offers 5-Night Stays for Two at the All-Inclusive Hideaway at Royalton Riviera Cancun in Cancun, Mexico, bundled with $150 Resort Credit, with prices starting from $1,442.92 via coupon code "SAVE50", as provided by Dunhill Travel. (It's the top offer on the page; we found this rate on September 3.) At $289 per night, that's the lowest price we could find by $285. This 4-star adults-only resort has an Expedia rating of 83% based on 337 reviews. Book this travel deal by July 30 for stays from September 3 through October 27.

BookIt offers a 5-Night Stay for Two at the All-Inclusive Melia Puerto Vallarta in Puerto Vallarta, Mexico, with prices starting at $1,225 via code "SAVE50", as provided by Dunhill Travel. (It's the first offer on the landing page; We found this rate on October 2.) At $245 per night, that's the lowest price we could find by $50. This 4-star hotel has an Expedia rating of 81% based on 1,196 reviews. Additional taxes and fees apply. Book this travel deal by July 28 for stays from September 4 through November 27.