Caribbean Vacations

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4-Star Renaissance Aruba Trips w/Air

 
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Stay in the heart of Oranjestad at one of the top resorts on the islandExpires: 11-03-2016jetBlue Getaways

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All-Inclusive Sale up to 65% OFF + Extra $100 at Checkout

$679.00$1,499.00
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Save on 7+ night vacation packages through March w/code ALLIN100Expires: 09-30-2016CheapCaribbean

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Caribbean 7-Night Packages at $300 OFF

 
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Pick from Puerto Rico, Barbados and moreExpires: 11-25-2016Priceline

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

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

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Top-Rated Atlantis Resort up to 50% OFF

$159+
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Up to $150 in resort credit + FREE Shallow Water Dolphin InteractExpires: 11-16-2016Priceline

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Extra $100 OFF Any Flight & Hotel Vacation

$289+
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FREE nights, room upgrades and more in Hawaii, Mexico, Europe Expires: 10-25-2016Orbitz

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Turks & Caicos Upscale Getaway at $640 OFF

 
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Includes air and stays at beachfront Windsong ResortExpires: 10-13-2016CheapCaribbean

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Luxury Bahia Principe Packages at 35-45% OFF

$489.00$849.00
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Unlimited a la carte dining, 24hr room service, poolside wait service, moreExpires: 10-25-2016CheapCaribbean

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Deluxe Cayman Islands Packages w/Air 45% OFF

$809.00$1,459.00
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Bonus: Take Extra $150 off with Coupon Code CAYMAN150Expires: 10-21-2016CheapCaribbean

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Turks & Caicos: 6 Nts w/Air at $520 OFF

$679.00$1,199.00
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Pick from over a dozen resorts (some all-inclusive)Expires: 11-19-2016CheapCaribbean

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Last-Minute Caribbean Cruise Deals

 
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Includes All-Inclusvie resorts + R/T flightsExpires: 11-29-2016Apple Vacations

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Hard Rock Punta Cana Vacation Deal

$1,289.00$1,709.00
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All-inclusive stays for 4 nights + airExpires: 09-29-2016CheapCaribbean

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"The Best Of Apple Vacations" Discounted (Inl. Air)

$599+
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Save on the best of the best winter spots in Mexcio, Hawaii and the Caribbean - book by 10/6Expires: 10-06-2016Apple Vacations

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Sunscape Resort Vacations at $350 OFF

$779.00$1,129.00
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Save up to 50% off your stay + up to $400 in resort couponsExpires: 11-10-2016CheapCaribbean

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Marriott Resort Sale - 5 Nts & Air

 
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Pick from stays across the Caribbean and MexicoExpires: 10-06-2016CheapCaribbean

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7 Nts at Sandals + $1000 Air Credit

$674
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Save up 65% + vacation in absoute luxuryExpires: 11-17-2016Sandals Resorts

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Upscale Jamaica Getaways, Incl. Air

$599+
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Pick from top all-inclusive beachfrton resortsExpires: 10-05-2016jetBlue Getaways

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Luxury Jamaica: 5 All Inclusive Nts/Air

$1,099.00$2,599.00
2.5% Donation
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Up to 45% Off + $200 Instant Flight Credit Expires: 10-20-2016BookIt.com

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Club Med "Break Free" Sale

$169+
0% donation
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Up to 50% OFF all-inclusive escapes + up to $300 air creditExpires: 10-05-2016Club Med

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All-Inclusive Sale - 4 Nt Trips at $400+ OFF

$569.00$1,049.00
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Luxury stays + air to Cabo, Punta Cana, Cancun, Costa Rica, moreExpires: 10-11-2016CheapCaribbean

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Cuba Introductory Fare from Ft. Lauderdale

$99.00
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Special non-stop flight to Santa Clara, Camag├╝ey and HolguinExpires: 10-05-2016JetBlue Airways

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6-Apple "Unlimited" Vacations at 1/2 OFF

$529+
Up to $36 Donation
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Stay at luxury AMResorts across Mexico and the Caribbean w/extra $200 in resort couponsExpires: 10-31-2016Apple Vacations

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6-Apple Unlimited Vacations at 1/2 OFF

$529+
Up to $36 Donation
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Stay at luxury AMResorts across Mexico and the Caribbean w/extra $200 in resort couponsExpires: 10-31-2016Apple Vacations

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Upscale Puerto Rico Trip over $400 OFF

$529.00$969.00
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Includes stays at the Wyndham Grand Rio Mar Beach Resort + R/T flightsExpires: 11-19-2016CheapCaribbean

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International Deulxe Fall Tours up to $889 OFF

$459+
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Save up to 30% on trips to Italy, Australia, South America, and the U.S. Expires: 09-28-2016Contiki

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All-Inclusive Holiday Vacation Deals

$729+
Up to $36 Donation
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Incredible deals on December travel to all-inclusive tropical resorts + resort creditExpires: 10-13-2016Apple Vacations

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Turks & Caicos Getaways w/Air (Save $300+)

$699.00$1,439.00
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Choose from beachfront hotels to deluxe all-inclusve resortsExpires: 10-28-2016CheapCaribbean

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Huge Winter All-Inclusive Vacation Sale

$729+
Up to $36 Donation
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Early-bird savings up to 50% OFF luxe packages to the Caribbean and MexicoExpires: 09-29-2016Apple Vacation

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Winter 2017 Getaways w/Air on Sale

$649.00$1,499.00
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Trips discounted to all-inclusive beachfront resorts across the Caribbean and Mexico Expires: 09-30-2016CheapCaribbean

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Select Luxury AMResort Vacations at 50% OFF

$899.00$1,835.00
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Pick from luxury beachfront all-inclusive stays in Cancun, La Romana, Cabo, and JamaicaExpires: 10-24-2016Apple Vacations

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Last Minute Caribbean Getaways w/Air

 
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Includes deluxe hotel and roundtrip flightsExpires: 12-08-2016Apple Vacations

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.