Caribbean Vacations

Caribbean Deals

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One Week Sale on January Vacations

$599+
Up to $36 Donation
Donation applies when you are logged in with a selected cause.

Stay up to seven nights at luxe all-inclusive resorts in Cancun, Punta Cana, Cabo, Jamaica and moreExpires: 02-01-2017Apple Vacations

Priceline_Caribbean-Vacations_Caribbean-7-Night-Packages-at-$300-OFF

Caribbean 7-Night Packages at $300 OFF

 
Up to 8% Donation
Donation applies when you are logged in with a selected cause.

Pick from Puerto Rico, Barbados and moreExpires: 02-18-2017Priceline

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Top-Rated Atlantis Resort up to 50% OFF

$159+
Up to 8% Donation
Donation applies when you are logged in with a selected cause.

Up to $150 in resort credit + FREE Shallow Water Dolphin InteractExpires: 02-10-2017Priceline

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St. Maarten Luxe Getaway w/Air

$929.00$1,629.00
1.5% Donation
Donation applies when you are logged in with a selected cause.

PIck from 4 to 6-night escapes - valid for travel next spring and summerExpires: 01-25-2017CheapCaribbean

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Last-Minute Caribbean Cruise Deals

 
Up to $36 Donation
Donation applies when you are logged in with a selected cause.

Includes All-Inclusvie resorts + R/T flightsExpires: 02-17-2017Apple Vacations

CheapCaribbean_Family-&-Theme-Park-Vacations_All-Inclusive-Riu-Vacations-up-to-$470-OFF

All-Inclusive Riu Vacations up to $470 OFF

$699.00$1,009.00
1.5% Donation
Donation applies when you are logged in with a selected cause.

Pick from stays in Costa Rica, Punta Cana, Bahamas, even St. MartinExpires: 03-09-2017CheapCaribbean

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Marriott Resort Sale - 5 Nts & Air

 
1.5% Donation
Donation applies when you are logged in with a selected cause.

Pick from stays across the Caribbean and MexicoExpires: 03-24-2017CheapCaribbean

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$539+ Luxury Bahia Principe Trips w/Air

 
Up to $36 Donation
Donation applies when you are logged in with a selected cause.

Includes golf and spa discounts, VIP in-room amenities, moreExpires: 02-16-2017Apple Vacations

CheapCaribbean_Caribbean-Vacations_Aruba-5+-Nt-Vacations-w/Air-at-$400-OFF

Aruba 5+ Nt Vacations w/Air at $400 OFF

$999.00$1,699.00
1.5% Donation
Donation applies when you are logged in with a selected cause.

Pick from beachfront hotels to luxury all-inclusive resortsExpires: 01-26-2017CheapCaribbean

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4-Star Bahamas Getaway w/Air

 
1.5% Donation
Donation applies when you are logged in with a selected cause.

Stay at a condo with kitchens, living rooms with sleeper sofas, and dining areasExpires: 01-24-2017CheapCaribbean

Contiki_Family-&-Theme-Park-Vacations_2016-Europe-&-Asia-Tours-up-to-$900-OFF

2016 Europe & Asia Tours up to $900 OFF

$250+
2.5% Donation
Donation applies when you are logged in with a selected cause.

Discounts on dozens last-minute fall and winter experiences Expires: 03-17-2017Contiki

CheapCaribbean_Caribbean-Vacations_Cayman-Islands-Vacations-at-$450+-OFF

Cayman Islands Vacations at $450+ OFF

$829.00$1,299.00
1.5% Donation
Donation applies when you are logged in with a selected cause.

Hundreds OFF stays through December + extra $150 OFF w/code 150CAYMANExpires: 02-10-2017CheapCaribbean

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Winter Holiday Deals Across the Caribbean

$144.00$361.00
2.5% Donation
Donation applies when you are logged in with a selected cause.

Bonus: Extra 10% OFF resort bookings/Extra $100 OFF air-inclusive packagesExpires: 02-16-2017BookIt.com

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7 Nts at Sandals + $1000 Air Credit

$149+
2% Donation
Donation applies when you are logged in with a selected cause.

Save up 65% and vacation in absolute luxury in the CaribbeanExpires: 02-16-2017Sandals Resorts

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Jamaica on Sale - 4 Beachfront Nts w/Air

$549.00$1,109.00
1.5% Donation
Donation applies when you are logged in with a selected cause.

Pick from beachfront to all-inclusive resorts - valid for travel this winter and spingExpires: 01-31-2017CheapCaribeean

Caribbean Vacation Deals

The Caribbean is a stunning tropical vacation destination that comes with a surprisingly low price tag.

Caribbean Description

The Caribbean is an island paradise with a diverse selection of vacation experiences for visitors to enjoy. Though the Caribbean comprises more than 700 islands, just 2 percent of them are inhabited, providing a wild escape with many destinations that feel delightfully untouched by developers. You can go diving in the clear blue waters around the Cayman Islands, hit the casinos in Aruba, or explore the jungles and caves of Belize. You can enjoy a secluded couple's escape in the U.S. Virgin Islands, or take the whole family for a week of larger-than-life adventures at an all-inclusive Jamaican resort. With so many choices, the Caribbean is an ideal pick for parties who want a little of everything. It's easy to please family members who want adventure alongside those who want to sun themselves or shop at this destination.

The Best Time of Year to Visit the Caribbean

The Caribbean enjoys warm weather year-round, making it a popular destination in any season. The busiest time for tourism in the Caribbean is from December to April, when travelers seek refuge from cold northern winters. This is also the driest part of the year, making it a popular pick for those who want to avoid storms. May through June is a shoulder season, offering moderate rain and smaller crowds. If you're looking for affordable travel deals, this is one of the best times to go. July through October is hurricane season and is the least popular time to head to the Caribbean. However, these storms can create a favorable surf in the eastern Caribbean, and room prices are pleasantly low.

Cheapest Hotels in the Caribbean

When you take all your travel expenses into consideration, the least expensive hotels in the Caribbean are typically the all-inclusive resorts. These give you far more than just a bed to sleep in, offering perks that include meals, recreation, and unparalleled beach access in many locations. Some of the least expensive picks in the islands are in the Dominican Republic's Puerto Plata, Punta Cana, and La Romana districts. Jamaica's Negril and Ocho Rios districts are among the least expensive options as well. If you're looking for something outside the all-inclusive category, consider Anacanoa in Meads Bay Anguilla, Admiral's Inn in English Harbour, Antigua, or the Staniel Cay Yacht Club in the Exuma Cays, Bahamas.