Caribbean Sweepstakes
Found 11 total
Enter the United Vacations Email Giveaway to win an unforgettable getaway. One lucky winner will receive a three-night stay for two adults in a standard hotel room at any participating RIU Resort in Mexico or the Caribbean, with an Approximate Retail Value of $2,000.00. Don't miss this free entry opportunity to win a fantastic prize from United Vacations.
Win $2,000 in value – United Vacations Email Giveaway - Enter Now
Enter the MSC Cruises 7-Night Caribbean Cruise Sail Into Paradise Cruise Giveaway Sweepstakes, sponsored by OLA Vacations, Inc., for a chance to win a fantastic cruise prize. This exciting giveaway offers a balcony cabin for two on an MSC Cruises 7-Night Caribbean cruise, with an approximate retail value of $3,200. To enter, simply visit the sweepstakes site and complete the entry form, or use the free alternate method of entry by mailing in a 3x5 card with your contact information. The promotion period runs from May 13, 2026, to June 12, 2026, and is open to legal residents of the United States and the District of Columbia who are at least 21 years old. One entry per person is allowed, and the winner will be selected in a random drawing on or about June 22, 2026. Don't miss this opportunity to sail into paradise with OLA Vacations, Inc. and MSC Cruises.
Enter the NEA Member Benefits FY26 Annual Giveaway Sweepstakes for a chance to win a fantastic prize. Between April 6, 2026, and June 29, 2026, NEA members can enter by registering at www.neamb.com or calling 1-800-637-4636, providing their complete name, mailing address, and email address. Limited to one entry per eligible NEA member per day, with a total of two potential winners to be selected in a random drawing. The prize includes a cruise certificate for a four-night cruise to Mexico or the Caribbean, plus $250 in Vacation Cash, with an approximate retail value of $950. Open to NEA members who are 18 years or older and legal residents of the U.S. or the District of Columbia. Enter to win this amazing giveaway, courtesy of NEA Member Benefits.
Win $950 in value – NEA Member Benefits FY26 Annual Giveaway Sweepstakes - Enter Now
Enter the Miracle Made Cruise Sweepstakes to win a grand prize package valued at $2,400. One lucky winner will receive a $1,500 Royal Caribbean gift card to redeem on a cruise of their choice, a $600 Kayak gift card for roundtrip airfare, and a $300 Royal Caribbean gift card for onboard expenses. Don't miss this chance to set sail with Royal Caribbean - enter to win your dream cruise getaway today.
Win $2,400 in value – Miracle Made Cruise Sweepstakes - Enter Now
Enter the Wheel of Fortune Carnival Spin & Sail Giveaway for a chance to win one of five exciting sweepstakes prizes, each with a total approximate retail value of $7,244.88. From May 18th to May 22nd, 2026, winners can choose from a range of Carnival Cruise Line itineraries, including Mexican Riviera, Eastern Caribbean, Western Caribbean, and General Caribbean, for an up to 10-day cruise. Don't miss this opportunity to sail away with a free entry to win a prize. The giveaway ends at 2:59 AM PST on May 30, 2026, so enter now for your chance to set sail with Carnival Cruise Line.
Pro Tips : This is a multi-day promotion (e.g., one week with daily individual sweepstakes for different cruise prizes). The overall entry window is usually open for about 7 days (with the last entry period ending shortly after the final episode), but you must return each day after watching the episode to submit the Bonus Round puzzle solution for that day's drawing.
You need a free Wheel Watchers Club account (SPIN ID) to enter.
Entries are tied to each day's episode, missing a day means missing that day's chance. There are 5 individual Wheel of Fortune Sweepstakes. 5 separate daily cruises.
Win $36,244 in value – Wheel of Fortune Carnival Spin & Sail Giveaway - Enter Now
Enter to win the CharityBuzz Magical VIP Weekend Sweepstakes for a chance to experience the ultimate Disney getaway. One lucky winner and up to three guests will receive a prize package valued at $51,185.93, including round-trip airfare to Southern California, a two-night stay at the Disneyland Hotel Pirates of the Caribbean Suite, VIP tours, and Disneyland Resort Park Hopper tickets. Enjoy dinner at Napa Rose, attend the Avengers: Doomsday premiere with red carpet access, and receive a $10,000 cash payment. Enter the CharityBuzz Magical VIP Weekend Sweepstakes for free and take a shot at this magical prize.
Win $51,185 in value – CharityBuzz Magical VIP Weekend Sweepstakes - Enter Now
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 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
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
