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Caribbean Vacations: Packages & Deals*

*Some taxes, fees extra. Vacation prices are per person, based on double occupancy, unless noted.
$3499 & up -- Cuba: 8-Nt. Escorted City & Beach Trip w/Air
 
Source: smarTours | By Veronica Crews

Highlights include riding in vintage cars, cigar making and a visit to the home of Ernest Hemingway
Select dates in 2017

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Source: Pleasant Holidays

This Riu resort opened just this summer; this is part of a larger sale including family-friendly Punta Cana vacations
Select dates through Dec. 15

 
Source: Apple Vacations

This all-inclusive deal includes a three-night stay at one of the top 15 hotels in Punta Cana (TripAdvisor) and includes nonstop air from Chicago
Select dates, November-December

 
Source: CheapCaribbean.com

Spend four nights at a 4-star resort in Punta Cana with this deal that includes a Jr. Suite room upgrade and airfare.
September-October; discounted thru April

 
Source: CheapCaribbean.com

This 4-star all-inclusive Riu resort boasts in-room liquor dispensers and guests also receive at $1250 resort credit with this deal
September-October; discounted thru April

 
Source: CheapCaribbean.com

The 4-star Grand Palladium is located on a prime stretch of award-winning Bavaro Beach in Punta Cana
September-December; discounted thru April

 
Source: CheapCaribbean.com

This deal includes $200 in resort credits.
Dates through December, discounts through April

 
Source: Pleasant Holidays

Save $100 on this Atlantis vacation, which also includes a $250 resort credit per room; kids stay and eat for free
Select dates through Dec. 15

 
Source: Pleasant Holidays

This sale includes beach vacations to Aruba, the Bahamas, Bermuda, Dominican Republic, Jamaica and Puerto Rico
Select dates through Dec. 15

 
Source: Liberty Travel

Stay at a 4-star villa beach resort in St. Lucia with this deal that includes air, a four-night stay and transfers
Dec. 4-8

 
Source: CheapCaribbean.com

This deal includes a free upgrade to a room with partial water views.
Select dates thru December; discounted thru April

 
Source: CheapCaribbean.com

The all-inclusive Grand Palladium Jamaica boasts a huge infinity pool that looks out over the ocean
September-December; discounted thru May

 
Source: Friendly Planet

This comprehensive escorted Cuba itinerary includes stops in Havana, Cojimar, Las Terrazas, Varadero, Cardenas, Coliseo and Matanzas
Select December-April dates

 
Source: CheapCaribbean.com

Two kids stay and eat free at this all-inclusive Riu resort, plus travelers will receive a $500 resort credit with this deal.
September-December; discounted thru April

 
Source: Puerto Rico

Puerto Rico stands out as an easy Caribbean vacation with 22 nonstop flights, no U.S. passport requirement, white sand beaches, and more.
2016 Travel

 
Source: Cheap Caribbean

Stay in a junior suite with personal butler service and a balcony.
Select dates through October, discounts thru April

 
Source: Cheap Caribbean

The Sunscape Curacao Resort has a massive in-house dive center for snorkeling and scuba.
Select dates November - December

 

More Deals on Caribbean Vacations *

 
Select dates through Dec. 6
Pleasant Holidays
 
Through Oct. 30
British Virgin Islands Tourism Board
 
2016 & 2017 travel
Cayman Islands Tourism
 

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Caribbean Vacation Tips
Each Caribbean location has its own culture and traditions, offering everything from historical stays to relaxing beachfront escapes. Travelers can choose from popular spots like Jamaica, Puerto Rico, the Bahamas, the Dominican Republic and more.

Popular among families and people looking for an easy escape, all-inclusive packages are common here at budget-friendly as well as luxurious properties. These packages tend to include flights, hotel stays, meals and some activities.

Prices are most reasonable June-November, which is hurricane season in the Caribbean. Aruba, Bonaire and Curacao are popular during those months because they fall outside of the hurricane belt. The most popular time to visit are mid-December into April, and prices can shoot up over spring break times.

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