Caribbean Vacations

Caribbean Deals

CheapCaribbean_Caribbean-Vacations_Deluxe-Cayman-Islands-Packages-w/Air-45%-OFF

Deluxe Cayman Islands Packages w/Air 45% OFF

$809.00$1,459.00
1.5% Donation
Donation applies when you are logged in with a selected cause.

Bonus: Take Extra $150 off with Coupon Code CAYMAN150Expires: 01-13-2017CheapCaribbean

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

Priceline_Caribbean-Vacations_Deluxe-Puerto-Rico:-7-Nts-w/Air-from-$699

Deluxe Puerto Rico: 7 Nts w/Air from $699

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

Choose from stays in San Juan to beachfront resortsExpires: 12-15-2016Priceline

Apple-Vacations_Family-&-Theme-Park-Vacations_Last-Minute-&-Holiday-All-Inclusive-Vacations-50%-OFF

Last-Minute & Holiday All-Inclusive Vacations 50% OFF

$799+
Up to $36 Donation
Donation applies when you are logged in with a selected cause.

Stay 7 nights with resort coupons at select resorts like Secrets, Dreams, and SunscapeExpires: 12-22-2016Apple Vacations

Orbitz_Mexico-Vacations_Extra-$100-OFF-Any-Flight-&-Hotel-Vacation-

Extra $100 OFF Any Flight & Hotel Vacation

$289+
Up to 5% Donation
Donation applies when you are logged in with a selected cause.

FREE nights, room upgrades and more in Hawaii, Mexico, Europe Expires: 12-28-2016Orbitz

Apple-Vacations_Caribbean-Vacations_Last-Minute-Caribbean-Cruise-Deals

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_Caribbean-Vacations_Luxury-Bahia-Principe-Packages-at-35-45%-OFF

Luxury Bahia Principe Packages at 35-45% OFF

$489.00$849.00
1.5% Donation
Donation applies when you are logged in with a selected cause.

Unlimited a la carte dining, 24hr room service, poolside wait service, moreExpires: 12-29-2016CheapCaribbean

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

CheapCaribbean_Caribbean-Vacations_Sunscape-Resort-Vacations-at-$350-OFF

Sunscape Resort Vacations at $350 OFF

$779.00$1,129.00
1.5% Donation
Donation applies when you are logged in with a selected cause.

Save up to 50% off your stay + up to $400 in resort couponsExpires: 12-21-2016CheapCaribbean

CheapCaribbean_Caribbean-Vacations_Marriott-Resort-Sale---5-Nts-&-Air

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

jetBlue-Getaways_Caribbean-Vacations_Upscale-Jamaica-Getaways,-Incl.-Air

Upscale Jamaica Getaways, Incl. Air

$599+
1.5% Donation
Donation applies when you are logged in with a selected cause.

Pick from top all-inclusive beachfrton resortsExpires: 12-23-2016jetBlue Getaways

Apple-Vacations_Mexico-Vacations_$539+-Luxury-Bahia-Principe-Trips-w/Air-

$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

Contiki_International-Vacations_International-Deulxe-Fall-Tours-up-to-$889-OFF

International Deulxe Fall Tours up to $889 OFF

$459+
2.5% Donation
Donation applies when you are logged in with a selected cause.

Save up to 30% on trips to Italy, Australia, South America, and the U.S. Expires: 01-20-2017Contiki

CheapCaribbean_Mexico-Vacations_Winter-2017-Getaways-w/Air-on-Sale

Winter 2017 Getaways w/Air on Sale

$649.00$1,499.00
1.5% Donation
Donation applies when you are logged in with a selected cause.

Trips discounted to all-inclusive beachfront resorts across the Caribbean and Mexico Expires: 12-24-2016CheapCaribbean

Marriott_Caribbean-Vacations_Marriott-4-Nt-Caribbean-Trips-w/Air

Marriott 4-Nt Caribbean Trips w/Air

$545+
2% Donation
Donation applies when you are logged in with a selected cause.

Hundreds off trips to luxury properties in St. Kitts, Aruba, Puerto Rico and moreExpires: 12-29-2016Marriott

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: 12-15-2016CheapCaribbean

bookit.com_Caribbean-Vacations_Winter-Holiday-Deals-Across-the-Caribbean

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: 12-12-2016BookIt.com

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.