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Caribbean Vacations: Packages & Deals*

*Some taxes, fees extra. Vacation prices are per person, based on double occupancy, unless noted.
$899 & up -- Jamaica: Weeklong All-Inclusive Trip w/Air
 
Source: Apple Vacations | By Travelzoo Staff

This all-inclusive beachfront resort features an infinity pool larger than a football field -- the largest on the island
Select departures in September

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Source: Vacation Express

This 4-star resort's water park has a wave pool and more than a dozen slides for kids and adults.
Select dates through Dec. 19

 
Source: CheapCaribbean.com

This all-inclusive deal includes all meals and drinks, a bottle of rum and resort credit
Select dates August-December; discounted thru Apri

 
Source: CheapCaribbean.com

Spend five nights in the Caribbean with this budget-friendly deal -- or upgrade to a 4-star resort for $120 more per person
Select dates September-December

 
Source: CheapCaribbean.com

All meals and drinks are included in the nightly rate -- that’s less than the cost of a typical dinner for two -- as well as VIP beach access
September-October

 
Source: Apple Vacations

This 4-star, all-suite beachfront resort features eight restaurants, four bars, two outdoor pools, two hot tubs and a dive center
Aug. 29; Sept. 19; more dates on sale

 
Source: Apple Vacations

This November, check out a brand new Punta Cana resort along Bavaro Beach with this all-inclusive deal including air
Select departures, November-December

 
Source: CheapCaribbean.com

Spend three nights at an all-inclusive resort with this deal that saves $400 on regular pricing
August-October; discounted thru April

 
Source: CheapCaribbean.com

This all-inclusive getaway includes a stay at a 4-star resort that TripAdvisor users rate in the top five hotels in the area
August-October; discounted thru April

 
Source: CheapCaribbean.com

This four-night trip includes airfare, all meals and drinks plus kids stay and eat free
August-October; discounted thru April

 
Source: Liberty Travel

This 4-star beach resort features two pools, six restaurants. eight bars, a spa and a children's water park
Oct. 26-30

 
Source: CheapCaribbean.com

This four-night trip includes resort credit and kids stay and eat free
Select dates August-October; discounted thru April

 
Source: smarTours

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

 
Source: Friendly Planet

This comprehensive escorted Cuba itinerary includes stops in Havana, Cojimar, Las Terrazas, Varadero, Cardenas, Coliseo and Matanzas
October travel; additional 2016-2017 available

 
Source: CheapCaribbean.com

This member-favorite resort in Montego Bay covers all meals and drinks on this four-night stay
August-October; discounted thru April

 
Source: CheapCaribbean.com

This four-night getaway includes all meals and drinks and a stay at a luxury resort
Select dates August-October; discounted thru April

 
Source: CheapCaribbean.com

Spend four nights at a luxury all-inclusive, adults-only resort with this deal that saves $420 on regular pricing
August-October; discounted thru April 2017

 
Source: CheapCaribbean.com

This is one of the lowest-priced Aruba vacations we've seen in years
Select August-December dates

 
Source: CheapCaribbean.com

This hotel is steps from Seven Mile Beach and surrounded by resorts that cost twice as much
Select dates through December

 
Source: Atlantis, Paradise Island, Bahamas

Atlantis launched an all-inclusive package with exclusive Travelzoo extras, so guests can eat, drink and enjoy activities for one flat price.
Travel Aug. 17 - Dec. 20; three-night minimum stay

 
Source: Vacation Express

No need to shell out cash for meals & drinks at this all-inclusive resort, a rarity in the Bahamas.
Select dates through December

 
Source: Liberty Travel

Set on two miles of beach, this San Juan resort has five restaurants, 24 hour room service, a casino and a pool with a swim-up bar
Nov. 6-10

 
Source: JetBlue Getaways

Save 45% on a stay at The Crane Resort Residences, set on Crane Beach
Sept. 19, 26

 
Source: CheapCaribbean.com

This 4.5-star getaway includes an upgrade to a partial water view room plus all meals and drinks
August-December

 
Source: JetBlue Getaways

Stay at the Time Out Hotel & get daily breakfast for two people
Sept. 19, 26

 

More Deals on Caribbean Vacations *

 
 
 
Select dates September-December
CheapCaribbean.com
 
Dec. 17; additional dates on sale
Apple Vacations
 
Through Oct. 30
British Virgin Islands Tourism Board
 
 
 
 
 
 
Select dates September-December
CheapCaribbean.com
 
Select dates September-December
CheapCaribbean.com
 
Select dates September-December
CheapCaribbean.com
 
Select departues through June 4, 2017
Sun Country Airlines
 
 
 
 
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.