enter online and win free caribbean sweepstakes and contests

Winning Caribbean Sweepstakes is a great way to travel to the Caribbean for free. Jamaica, the Cayman Islands, the Bahamas, the Dominican Republic and all the other Caribbean islands have beautiful scenery and are tropical paradises throughout the year. Which island would you like to go to?

Many Caribbean Sweepstakes offer trips to the Sandals and Beaches Resorts while many other Caribbean Sweepstakes offer trips to the Atlantis Hotel and Resort.

If you are craving to win a free trip to the Caribbean, then visit SweepstakesMania for the best Caribbean Sweepstakes!!

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Sixlets Family Caribbean Cruise Getaway Sweepstakes

SweetWorks Confections is sponsoring a sweepstakes called Sixlets Family Caribbean Cruise Getaway Sweepstakes in which you could win a 4-day Caribbean Disney Cruise! Trip includes roundtrip airfare for four (1 winner)! The sweepstakes ends December 31, 2017 and each person can enter once daily. Each entrant must be a legal resident of the   United States (or […]

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ELLEN Moon Palace Jamaica Grande! Sweepstakes

WAD Productions is sponsoring a sweepstakes called the ELLEN Moon Palace Jamaica Grande! Sweepstakes in which you could win a trip for two to the Moon Palace Jamaica Grande (1Winner)! The sweepstakes ends September 4, 2017 and each person can enter once. Each entrant must be a legal resident of the 50 United States (or the […]

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JetBlue Ocean Spray Sweepstakes

JetBlue Airways is sponsoring a sweepstakes called the JetBlue Ocean Spray Sweepstakes in which you could win a trip a JetBlue Vacation Package to either Bermuda, Aruba, or Puerto Rico including $1,000 for accommodations, and a case of Ocean Spray Mocktails (3 Winners)! The sweepstakes ends August 28, 2017 and each person can enter once weekly. […]

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Sky Delta Dream It, Win It! Sweepstakes

Delta Sky is sponsoring a sweepstakes called the Sky Delta Dream It, Win It! Sweepstakes in which you could win a 4-night trip for two to Aruba, a William Leather Duffel Bag, and an Avery Leather Tote Bag (1 Winner)! The sweepstakes ends August 31, 2017 and each person can enter once. Each entrant must be a legal […]

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Oprah Magazine Adventure of Your Life Cruise Contest

Oprah Magazine is sponsoring a sweepstakes called the Oprah Magazine Adventure of Your Life Cruise Contest in which you could win a 7-day Holland America Cruise for two to the Caribbean (1 Winner)! The sweepstakes ends on August 8, 2017 and each person can enter once. Each entrant must be a legal resident of the United States (or […]

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Hallmark Channel June Weddings Sweepstakes

Crown Media is sponsoring a sweepstakes called the Hallmark Channel June Weddings Sweepstakes in which you could win a 4-day/3-night trip for two to a Sandals Resort of your choice (1 Winner)! The sweepstakes ends on June 30, 2017 and each person can enter once daily. Each entrant must be a legal resident of the 50 United […]

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Jamaican Me Happy Escape Sweepstakes

Seagram Beverage Company is sponsoring a sweepstakes called the Jamaican Me Happy Escape Sweepstakes in which you could win a Seagram’s Escapes branded beach mat bag (100 winners) or a Seagram’s Escapes branded Ame & Lulu travel carry-on bag (10 winners) the grand prize is a trip for two to Jamaica (1 Winner)! The sweepstakes ends on […]

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Lands’ End Best on the Beach Sweepstakes

Land’s End is sponsoring a sweepstakes called the Lands’ End Best on the Beach Sweepstakes in which you could win a trip for two to Scrub Island, B.V.I., for an 8-day/7-night stay at Scrub Island Resort & Spa & Marina, meals, a Flexboat Rental, a $350 credit to Ixora Spa, and a $350 Lands’ End Gift Card! […]

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Cruzan Rum Bucket List Sweepstakes

Cruzan Rum Distillery is sponsoring a sweepstakes called the Cruzan Rum Bucket List Sweepstakes in which you could win a 5-day/4-night trip for two to St. Croix, U.S. Virgin Islands (1 Winner)! The sweepstakes ends on July 15, 2017 and each person can enter up to 18 times. Each entrant must be a legal resident of the 50 […]

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Mrs. Thinster’s “Baked With Love” Summer Sweepstakes

That’s How We Roll, LLC is sponsoring a sweepstakes called the Mrs. Thinster’s “Baked With Love” Summer Sweepstakes in which you could win a trip for four to Turks & Caicos, for a 5-day/4-night stay at Beaches Turks & Caicos (1 winner)! The sweepstakes ends on June 30, 2017 and each person can enter once. […]