Caribbean Sweepstakes
Found 7 total
Enter the Expedia Cruises Win a Dream Vacation 2026 Sweepstakes for a chance to win a 7-night Caribbean cruise for two, including roundtrip airfare, valued at up to $5,000. No purchase necessary. To enter, visit www.expediacruises.com and complete the entry form or enter in person at any Expedia Cruises location. Limit one entry per person, with additional entries available through referrals. Sweepstakes runs from January 1, 2026 to November 1, 2026. Winner will be selected in a random drawing on November 16, 2026. Expedia Cruises reserves the right to modify or cancel the sweepstakes. See official rules for details.
Win $5,000 in value – Expedia Cruises Win a Dream Vacation 2026 Sweepstakes - Enter Now
Enter the iHeartRadio Flea to Flee Giveaway for a chance to win an unforgettable Custom Caribbean Cruise Experience. This amazing prize, valued at $5,000.00, includes round-trip flights, a 5-night luxury Caribbean cruise, a 2-night hotel stay, pre-paid gratuities, $500 on-board spending credit, and round-trip airport/hotel/port transfers for you and up to three guests. The winner must redeem their prize within one year of being confirmed. Don't miss out - enter to win this incredible getaway before the sweepstakes ends on June 28, 2026, at 11:59:59 p.m. ET.
Win $5,000 in value – iHeartRadio Flea to Flee Giveaway - Enter Now
Enter the Margaritaville At Sea Heroes Cruise Giveaway for a chance to win a 7-night Caribbean cruise for two. This May, Margaritaville at Sea honors heroes like Teachers, Healthcare Workers, First Responders, and Military & Veterans. To win, share what makes your hero special. Twenty-four winners will receive a cruise certificate for a Breezy Balcony Stateroom aboard the Islander, with port taxes and fees covered by Margaritaville at Sea. Enter to win this incredible $1,798.00 USD prize, courtesy of Margaritaville at Sea, and give your hero an unforgettable getaway with ocean breezes, live music, and signature Margaritaville moments. Gratuities will be covered by the winner. Margaritaville at Sea brings you this amazing giveaway.
Win $43,200 in value – Margaritaville At Sea Heroes Cruise Giveaway - Enter Now
Royal Caribbean's Summer Greece Giveaway offers a chance to win a 7-night cruise to Greece with two Ultimate Santorini passes and a Grand Prize stateroom for you and a guest. Enter to win this free giveaway by following Royal Caribbean and commenting with who you'd bring along. The giveaway ends on May 17, 2026, at 11:59 PM. One winner will be selected to receive this amazing prize package, valued at approximately $10,000. Don't miss out on this opportunity to explore Greece with Royal Caribbean. Enter now for your chance to win this incredible sweepstakes prize.
Win $2,453 in value – Royal Caribbean Greece Cruise Giveaway - Enter Now
Enter the Hot Head Burritos Cinco de Montho Scratch Off Promotion Sweepstakes for a chance to win exciting prizes. The grand prize is a round-trip airfare and hotel accommodations for two to the Caribbean, valued up to $5,000, or $3,500 in cash. Other prizes include one free burrito a week for a year, $1 off any entree, free queso or guac, tortilla chips, burritos, bowls, and medium fountains. To redeem prizes, winners must sign up for the Hot Head Rewards App. No purchase is necessary to enter or win, and the sweepstakes is open to US residents 18 years or older. The promotional window begins on April 27, 2026, and ends on May 31, 2026. Enter on-site with a Scratch Off Ticket or via mail to Hot Head Franchising LLC. Limit one entry per person. With Hot Head Burritos, you can win big in this free entry sweepstakes. See official rules at https://hotheadburritos.com/locations. Hot Head Burritos is giving you the chance to win, so don't miss out.
Enter the USA Pickleball Association 2026 Golden Ticket Sweepstakes for a chance to win an incredible prize. One lucky winner will receive a four-day, three-night all-inclusive Caribbean vacation for two adults in a deluxe luxury room at any Sandals Resort, valued at $3,186.00. Don't miss this opportunity to win a dream getaway - enter to win the USA Pickleball Association 2026 Golden Ticket Sweepstakes today.
Win $3,186 in value – USA Pickleball Association 2026 Golden Ticket Sweepstakes - Enter Now
Get ready to win big with Our Usual Beach Travel 7-night Celebrity Cruise For 2 Giveaway, a thrilling sweepstakes that could send you on an unforgettable 7-night Caribbean cruise. This incredible prize, courtesy of Our Usual Beach Travel, includes a luxurious Veranda stateroom for two on any Celebrity ship sailing in the Caribbean, plus round-trip economy class airfare for two from Canada, courtesy of Air Canada. Enter to win this amazing $[prize value not mentioned] prize package for free before the deadline on December 14, 2026, and make your dream getaway a reality with Our Usual Beach Travel.
Win $5,000 in value – Our Usual Beach Travel 7-night Celebrity Cruise For 2 Giveaway - Enter Now
