Caribbean Sweepstakes
Found 8 total
Enter the Florida Panthers Hockey Club Sandals Ultimate Date Night Sweepstakes for a chance to win an incredible prize package. One lucky winner will receive a four-day, three-night all-inclusive Caribbean vacation for two at a select Sandals Resorts location, two airfare vouchers up to $500 per person, and two tickets to the Florida Panthers vs New York Rangers game on April 13th, 2026. The prize package is valued at $4,465 USD. Don't miss out on this amazing giveaway - enter to win your dream date night with the Florida Panthers Hockey Club and Sandals Resorts.
Where We Roam Podcast is giving away a $150 Royal Caribbean gift card or a $150 Disney Cruise Line gift card to put toward their next adventure. The contest ends Thursday, February 12, 2026, at 11:59 PM EST.
Win $300 in value – Where We Roam Podcast Gift Card Giveaway - Enter Now
Enter the A Luxe Caribbean Escape to S Hotel Montego Bay Sweepstakes for a chance to win a grand prize valued at $3,799. This incredible giveaway includes a 3-night all-inclusive stay for two in a Deluxe Ocean View Jr. Suite at S Hotel Montego Bay. The prize package also features gift cards from top brands: $500 from Daniela Shevel, $250 from Via Citrus, and $249 from Dink Eyewear, plus $100 in hydrating skincare products from RBA. Don't miss your chance to win this luxurious escape - enter now before entries close at 11:59 PM EST on February 27, 2026, courtesy of S Hotel Montego Bay.
Win $3,799 in value – A Luxe Caribbean Escape to S Hotel Montego Bay Sweepstakes - Enter Now
Enter the Chanice Fish Valentines Day Giveaway for a chance to win an unforgettable Caribbean Valentine's Experience for two. This romantic prize includes a 3-course dinner at Taste of the Caribbean on February 14. To win, simply enter by February 11, 2026, at 11:59 PM. Don't miss this free entry opportunity to win a dreamy getaway, courtesy of Chanice Fish.
Win $100 in value – Chanice Fish Valentines Day Giveaway - Enter Now
Enter the Raymour & Flanigan Winter Getaway Sweepstakes for a chance to win an unforgettable escape. Choose between a romantic Caribbean getaway for two in Nassau or St. Croix, complete with round-trip airfare and four nights at a resort, or a fun-filled family trip for four to Disneyland in California or Walt Disney World in Florida, including flights, hotel, and park hopper passes. With $9,000 in prizes up for grabs, submit your free entry before February 23, 2026, for a chance to win big with Raymour & Flanigan.
Win $9,000 in value – Raymour & Flanigan Winter Getaway Sweepstakes - Enter Now
Half Moon and MarryCaribbean.com are offering a Jamaica Contest 2026 dream escape: a five‑day, four‑night stay for two in an Estate Ocean room at the Eclipse enclave. Complete with the resort’s Complimentary Breakfast Plan. With crescent beaches, infinity pools, fine dining, and endless activities, every moment is designed to be unforgettable. MarryCaribbean.com Half Moon Jamaica Contest 2026 entries close on March 18, 2026, at 11:59 PM ET. Each finalist and winner must respond to notification within seven (7) days of the first notification attempt.
Win $500 in value – MarryCaribbean.com Half Moon Jamaica Contest 2026 - Enter Now
The Cunard’s Caribbean Voyage Sweepstakes grand prize provides a nine‑night Caribbean voyage for the winner and one eligible guest aboard Cunard’s Queen Elizabeth, sailing round‑trip from Miami from October 27 to November 5, 2026. The Cunard voyage package includes round‑trip coach airfare, one night of hotel accommodations in Miami before embarkation, a $200 onboard credit, all standard onboard meals and entertainment, and ground transportation between the airport, hotel, and cruise terminal. Altogether, the complete Cunard cruise experience carries an approximate retail value of $5,518 USD.
Win $5,518 in value – Cunard’s Caribbean Voyage Sweepstakes - Enter Now
Famadillo.com is bringing island flavor to one lucky winner with a $100 Taste of the Caribbean Gift Card. Entries close on February 28, 2026.
