Caribbean Sweepstakes
Found 8 total
Enter to win the World Travel Holdings Royal Caribbean Cruise Giveaway.
One winner gets a Royal Caribbean cruise voucher worth up to $5000 toward one balcony cabin.
Open to residents of the US, DC, Puerto Rico, US territories and Canada (excluding Quebec). Ends January 12, 2027 at 11:59 PM EST.
To enter, submit the entry form with your name, email and phone number on the Dream Vacations contest page. One entry per person.
Win $5,000 in value – World Travel Holdings Royal Caribbean Cruise Giveaway - Enter Now
Enter to win the TATSoul 20th Anniversary Giveaway Bishop Power Wand.
One winner gets a Bishop Power Wand full set with advanced battery (ARV $1300), with their choice of stroke. *The Bishop Power Wand is a pen-style, hybrid rotary tattoo machine created through a collaboration between Bishop Rotary and Critical Tattoo.
To enter, download the TATSoul app through the Gleam form, then earn bonus entries by subscribing to the newsletter, following @tatsoul on Instagram and referring friends.
Open to legal residents of the US, Canada, Mexico, Central America and the Caribbean countries listed in the rules. Ends October 31, 2026 at 11:59 PM PDT.
Win $1,300 in value – TATSoul 20th Anniversary Bishop Power Wand Giveaway - Enter Now
Enter to win the Tao Clean St Lucia Family Getaway Giveaway.
One winner receives a Caribbean family vacation for four: a 4-day/3-night beachfront stay in St. Lucia (listed ARV $3500).
To enter, use the entry link in the Tao Clean Instagram bio and complete the online form.
Open to 18+ US. Ends October 31, 2026 at 11:59 PM EDT.
Win $3,500 in value – Tao Clean St Lucia Family Getaway Giveaway - Enter Now
Enter to win the Warrior Winches Trail to SEMA Sweepstakes - 4 Winners.
Four winners receive Warrior winch prizes: Trojan 4000 lb portable utility winch; Sentinel 10000 lb winch with synthetic rope; Gladiator 10000 lb winch with extreme synthetic rope; and one combined Trojan plus Gladiator package (listed ARV $2500).
To enter, complete the Gleam entry actions at gleam.io/VsZHl/win-with-warrior-winches; bonus actions earn extra entries.
Open to 18+ US Canada Mexico Central America Caribbean (see Gleam). Ends November 2, 2026 at 11:59 PM CST.
Win $2,500 in value – Warrior Winches Trail to SEMA Sweepstakes - 4 Winners - Enter Now
Enter to win the Ecommerce Advisors Deluxe Caribbean Fall Break Sweepstakes.
One grand prize winner receives 3 nights at the Anse Marcel Resort (St. Martin) plus a $250 resort credit (total value $1,600).
To enter, submit your email on the DojoMojo entry page; sharing earns bonus entries.
Open to legal residents of the US and DC (excluding Alaska, Hawaii and Rhode Island) 18+. The vacation sweepstakes ends November 4, 2026 at 11:59 PM EST.
Win $1,600 in value – Ecommerce Advisors Deluxe Caribbean Fall Break Sweepstakes - 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
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
