Grand Cayman Sweepstakes
Found 4 total
Enter The Grandview Condos 5-Night Stay in Paradise on Grand Cayman Giveaway for a chance to win a dream vacation. One lucky winner will receive a 5-night stay in a 2-bedroom condo, accommodating up to 4 guests, on stunning Seven Mile Beach. Don't miss this free entry opportunity to win a paradise getaway - enter to win before the deadline of January 15, 2027.
Win $4,250 in value – Grandview Condos 5-Night Stay in Paradise on Grand Cayman Giveaway - Enter Now
Enter to win the "The Kimpton Seafire Resort & Spa 10th Anniversary Sweepstakes" for a chance to claim the Ultimate 10th Anniversary Hotel Stay grand prize. This incredible prize package, valued at $7,500, includes a 5-night stay in a luxurious Run of House Oceanview Room, round-trip airfare for two from Miami to Grand Cayman, daily breakfast, a signature celebration experience, and more. Don't miss this opportunity to win a unforgettable getaway to Kimpton Seafire Resort & Spa in Grand Cayman.
Win $7,500 in value – Kimpton Seafire Resort & Spa 10th Anniversary Sweepstakes - Enter Now
Enter the iHeartRadio JTV Mother’s Day Getaway Sweepstakes now for a chance to win an unforgettable Caribbean cruise. Log in with your iHeartRadio account or enter with Facebook or Google for a free entry. You could win a 6-night cruise to Grand Cayman, Mexico, and the Bahamas, complete with round-trip airfare, hotel stay, and ground transportation. The prize package, valued at $7,825, also includes an "All-Included" drinks and Wi-Fi cruise package, $1000 for meals and excursions, and a $1000 digital JTV Gift Card. Don't miss this iHeartRadio sweepstakes - enter to win by May 10, 2026, at 11:59:59 p.m. ET.
Win $7,825 in value – iHeartRadio JTV Mother’s Day Getaway Sweepstakes - Enter Now
Enter the Cayman Jack Road to Cinco Sweepstakes for a chance to win one of three exciting Grand Prizes. Each Prize includes a Janus Halcyon 250 Motorcycle, a Cayman Jack branded Sling bag, and a $1,000 check to cover additional expenses. With a total of three Grand Prizes available, winners will be selected from eligible entries in specific regions: Arkansas, Kansas, Oklahoma, or Texas; Arizona, California, Colorado, New Mexico, Nevada, or Utah; and Louisiana or Mississippi. The Approximate Retail Value of each Grand Prize is $15,485.00, with a Total Approximate Retail Value of all Grand Prizes being $46,455.00. Enter for free and take a shot at riding off into the sunset with Cayman Jack.
Win $46,455 in value – Cayman Jack Road to Cinco Sweepstakes - Enter Now
