Best Caribbean Vacation Packages & Travel Deals

BookIt offers 7-Night Stays for Two at the All-Inclusive Majestic Colonial in Punta Cana, Dominican Republic, bundled with a Round of Golf with prices starting at $1,133.75 via coupon code "1X100", as provided by ShermansTravel. (It's the top offer on the page; we found this rate on October 2.) That's the lowest current rate we could find for an all-inclusive, week-long stay at this property by $173. This 4-star hotel has an Expedia rating of 84% based on 3,305 reviews. Book this travel deal by September 30 for stays from September 29 through October 29.

Of note: An additional $48 golf cart fee applies.

Vacations to Go offers a Carnival Cruise 4-Night Western Caribbean Cruise for two with prices starting at $388. That's tied with last week's mention and the lowest price we could find for any such cruise this year by at least $50. This roundtrip cruise aboard the Carnival Fantasy departs from Miami, FL, on October 31 with stops in Key West, FL, and Cozumel, Mexico. Book this travel deal by November 2.

Vacations to Go offers a Norwegian Cruise Line 4-Night Jamaica Cruise for Two with prices starting from $398. That's a $160 drop from our August mention and $240 under the lowest price we could find for any such cruise in the next year. This roundtrip Caribbean cruise aboard the Norwegian Pearl departs from Miami, FL, on November 13 with one stop in Ocho Rios, Jamaica. Additional fees and taxes may apply. Book this travel deal by November 2.

Cruise.com offers a Royal Caribbean 5-Night Western Caribbean Cruise for Two with prices starting from $338, via the directions below, as provided by ShermansCruise. That's $40 under our August mention and an all-time low for any 5-night cruise. It's also the lowest price we could find by $50. This roundtrip cruise aboard the Empress of the Seas departs on October 1 from Miami, FL, with stops in Key West, FL, and Cozumel, Mexico. Book this travel deal by September 30. To get this offer:

1. On the top offer on the page, click on "See All Rates"
2. on the popup page, select the "Cruise.com" tab
3. click on "Get Started"
4. it's the top offer on the following page

Vacations To Go offers a Norwegian Cruise Line 7-Night Eastern Caribbean Cruise for Two with prices starting from $698. That's $100 under the lowest price we could find for a comparable cruise in October. This cruise aboard the Norwegian Escape departs from Miami, FL, on October 15 with stops in St. Thomas, U.S.V.I.; Tortola, British Virgin Islands; and Nassau, Bahamas. Additional fees may apply. Book this travel deal by November 1.

Vacations to Go offers a last minute Norwegian Cruise Line 4-Night Bahamas Cruise for Two bundled with a Complimentary Beverage Package with prices starting from $398. That's tied with our mention from last week and, assuming you use the drinks package it's also a savings of up to $632. This roundtrip cruise aboard the Norwegian Sky departs from Miami, FL, on October 17 and includes stops in Grand Bahamas Island and Nassau, Bahamas. Additional fees may apply. Book this travel deal by October 1.

CheapCruises offers a Carnival Cruise 4-Night Western Caribbean Cruise for Two with prices starting at $348. (Scroll down to find this date.) That's $20 under last week's mention and the lowest price we could find for this cruise by $80. This roundtrip cruise aboard the Carnival Sensation departs from Miami, FL, on December 1 with stops in Key West, FL, and Cozumel, Mexico. This travel deal ends November 1.

Vacations to Go offers a Royal Caribbean Cruise Line 7-Night Eastern Caribbean Cruise for Two bundled with $75 Onboard Credit with prices starting from $798. Assuming you use the credit, that's the lowest price we could find by $75. This roundtrip cruise aboard the Navigator of the Seas departs from Miami, FL, on November 27 and includes stops in Labadee, Haiti; San Juan, Puerto Rico; and Philipsburg, St. Maarten. Book this travel deal by November 1.

Virgin America offers select Virgin America 1-Way Fares Nationwide with prices starting at $40.10, as seen on Travelzoo. That's $3 under last week's mention and the lowest price we could find by $3. This price is valid on flights departing from Las Vegas, NV, (LAS) with arrival in Los Angeles, CA, (LAX) on September 27. This sale includes flights to San Francisco, CA, (SFO); Seattle, WA, (SEA); Dallas, TX, (DAL); and more. Book this travel deal by September 30 for travel on select dates from through November 9.

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

Apple Vacations cuts up to 50% off select AMResorts properties in Mexico, the Caribbean, and Central America, with prices starting from $549 per person. (Price is based on double occupancy.) These packages include roundtrip airfare, hotel transfers, hotel tax, resort baggage handling, fuel surcharges, and more. Book this travel deal by October 24 for vacations through December 15.

Cruise.com offers a Disney Cruise Line 3-Night Bahamas Cruise for Two with prices starting from $830 via the directions below, as provided by ShermansCruise. (Although ShermansCruise lists this cruise for $491 per person, we found lower rates at checkout.) That's tied with last week's mention and an all-time low for any Disney Cruise. It's also a current low by $40. This roundtrip cruise aboard the Disney Wonder departs from Port Canaveral, FL, on February 9, 2017 and includes stops in Castaway Cay, the Bahamas. Additional fees may apply. Book this travel deal by October 7. To get this offer:

1. On the top offer on the page, click on "See All Rates"
2. on the popup page, select the "Cruise.com" tab
3. click on "Get Started"
4. it's the top offer on the following page

Virgin America offers 500 Virgin America Elevate Points for free when you sign up to receive Virgin Sports emails. That's the best deal we've seen for Virgin America frequent flyer points. Deal ends September 30.

CheapCaribbean offers an All-Inclusive Grand Riviera Princess All Suites Resort 4-Night Flight and Hotel Package for Two in Riviera Maya, Mexico, in a Jacuzzi Junior Suite with prices starting at $1,025.52, as provided by ShermansTravel. (Note that this rate will appear higher on the booking page; it will drop during checkout.) That's $24 below our mention from last week and the lowest price we could find for this package by $238. This price is based on departure on October 30 from Ft. Lauderdale, FL, (FLL) with arrival in Cancun, Mexico, (CUN); other departure cities are available for an additional cost. This 4-star hotel has an Expedia rating of 79% based on 1,920 reviews. Book this travel deal by September 30 for stays through December 22.

Vacations to Go offers a Carnival Cruise 5-Night Mexico Cruise for Two with prices starting at $498. That's $60 under our mention from a month ago and the lowest rate we could find for any such Carnival cruise in October by at least $20. This roundtrip cruise aboard the Carnival Triumph departs from New Orleans, LA, on November 26 with stops in Cozumel and Progreso, Mexico. Additional fees and taxes may apply. Book this travel deal by October 1.

At Southwest Vacations, book a Flight and Hotel Vacation at a select Atlantis Paradise Island Resorts in Paradise Island, Bahamas, and get up to $500 Resort Credit for free. (A 3-night minimum stay is required.) This offer includes hotels like the The Cove Atlantis and Atlantis, Paradise Island Royal Towers. Additional fees and blackout dates may apply. Book this travel deal by December 20 for travel through April 24, 2017.

CheapCruises offers a Carnival Cruise 4-Night Western Caribbean Cruise for Two with prices starting at $358. (Although CheapCruises advertises prices from $169 on this date, the price increases at checkout.) That's the lowest price we could find for any such short cruise in November by $20. This roundtrip cruise aboard the Carnival Victory departs from Miami, FL, on November 28 with stops in Key West, FL, and Cozumel, Mexico. Additional fees and taxes apply. This travel deal ends October 1.

JetBlue via ShermansTravel offers select JetBlue Roundtrip Fares to the Caribbean with prices starting at $55.60. (On the ShermansTravel page, click on "JetBlue.com" in the main paragraph to see this rate.) That's $66 under the lowest price we could find for select routes on comparable airlines. This price is valid on flights departing from Fort Lauderdale, FL, (FLL) with arrival in Nassau, Bahamas (NAS) Rico, (BQN) on September 21. Book this travel deal by September 29 for travel through October.

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

CheapCruises offers a Carnival Cruises 4-Night Mexico Cruise for Two with prices starting from $358. That's the lowest price we could find for any such cruise in November by $40. This roundtrip cruise aboard the Carnival Inspiration departs on November 7 from Long Beach, CA, with stops in Catalina Island, CA, and Ensenada, Mexico. Additional fees may apply. Book this travel deal by November 1.

Cruise.com offers a Carnival Cruise 7-Night Bahamas Cruise for Two with prices starting at $838, as provided by ShermansTravel. (Scroll down and click on "Show me more departure dates" to see this option.) That's $80 less than any other such Carnival cruise in December. This roundtrip cruise aboard the Carnival Pride departs from Baltimore, MD, on December 4 with stops in Port Canaveral, FL; Nassau, Bahamas; and Freeport, Bahamas. Additional fees may apply. Book this travel deal by September 28.

Vacations to Go offers a Carnival Cruises 6-Night Eastern Caribbean Cruise for Two with prices from $758. That's tied with last month's mention and the lowest price we could find for any such October cruise by $120. This roundtrip cruise aboard the Carnival Conquest departs from Ft. Lauderdale, FL, on October 23 and stops in Half Moon Cay, Bahamas; Amber Cove, Dominican Republic; and Grand Turk, Turks and Caicos Islands. Additional fees may apply. Book this travel deal by October 1.