Grand Cayman Sweepstakes
Found 5 total
Enter to win the incredible "The Win A Trip To The Cayman Islands Sweepstakes" for a chance to escape to a tropical paradise. The grand prize, valued at approximately $11,515 CAD, includes round-trip Economy Class tickets for two on Air Canada from a major Canadian airport to the Cayman Islands, a 7-night stay at the Grand Cayman Marriott Resort, and a round of golf for two at North Sound Golf Club. To be eligible, trips must take place between January 11, 2027, and December 7, 2027. Don't miss your free entry to this amazing sweepstakes, ending November 30, 2026, at 11:59 pm EST.
Win $11,515 in value – The Win A Trip To The Cayman Islands Sweepstakes - Enter Now
Enter to win in The Cayman Jack EOD Escape Giveaway for a chance to escape with a grand prize. 20 lucky winners will each receive a $500 gift card to use for travel-themed services. The total retail value of all grand prizes is $10,000. Don't miss out - enter for free and take a shot at winning one of these exciting prizes before the sweepstakes ends at 11:59 p.m. ET on August 16, 2026, in this amazing giveaway by Cayman Jack.
Win $10,000 in value – Cayman Jack EOD Escape Giveaway - 20 Winners - Enter Now
Enter the Cayman Jack Escape-to-Paradise Sweepstakes for a chance to win a $25,000 grand prize to fund your dream getaway. Open to legal residents of the 50 United States or DC, 21 years or older, this sweepstakes runs from May 15, 2026, to September 14, 2026. To enter, visit https://www.caymanjack.com/sweepstakes/escape or scan the QR code on participating retail materials, then complete and submit the entry form. Limit one entry per person per day. Mark Anthony Brands Inc. is the sponsor of this sweepstakes, and by participating, entrants agree to abide by the official rules. The grand prize winner will be determined in a random drawing on or about September 15, 2026, and will receive a $25,000 check to use towards their escape-to-paradise getaway, courtesy of Mark Anthony Brands Inc.
Win $25,000 in value – Cayman Jack Escape-to-Paradise Sweepstakes - Enter Now
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
