Caribbean Vacation Sweepstakes

Win a Trip for 4 to Grand Cayman

by Travel Sweeps Blogger on June 24, 2017

Enter this sweepstakes for your chance to win a trip to Grand Cayman. The grand prize includes round trip travel for winner and 3 guests to Grand Cayman, one $2,000 Ritz-Carlton® gift card, and a $1,000 Visa® gift card! Everything you need for an awesome vacation! Deadline: July 31, 2017. https://www.southwest.com/flight/contest/2017137142717413

Enter this sweepstakes for your chance to win a trip for 2 to Scrub Island Resort, Spa & Marina in British Virgin Islands. The grand prize includes round-trip air transportation, 7 nights in a double occupancy ocean view suite, $350 credit to Ixora Spa, $350 Lands’ End gift card and more! Deadline: June 15, 2017. https://www.landsend.com/beachsweeps/

Win a Trip to Sint Maarten

by Travel Sweeps Blogger on March 17, 2017

Enter this sweepstakes for your chance to win a Caribbean vacation in Sint Maarten! The prize package includes 2 KLM economy class tickets to St. Maarten, 5 nights at the Holland House Beach Hotel, an island tour, and more! Deadline: March 26, 2017. https://a.pgtb.me/vx4SKn

Win a Trip for 2 to St. Croix

by Travel Sweeps Blogger on January 24, 2017

Are you ready to soak up some sun in the Caribbean? Enter this sweepstakes for your chance to win a trip to St. Croix! The grand prize winner will receive a 4-night stay in an oceanfront room at The Buccaneer, full breakfast daily, and money for travel. Deadline: Jan. 31, 2017. https://www.darbysmart.com/giveaways/wintergetaway

Win a 16 Night Luxury Vacation Throughout Florida and Jamaica

by Travel Sweeps Blogger on January 12, 2017

This is a big one! Enter Travel Channel’s “THE TRIP: 2017” sweepstakes for your chance to win a trip for two to Florida and Jamaica. The prize includes round-trip First Class air transportation, sixteen nights hotel accommodations, and $25,000 spending money! Alternatively, in lieu of receiving the trip package, the grand prize winner may elect to receive $75,000. Decisions, decisions! Deadline: March. 24, 2017. http://www.travelchannel.com/sweepstakes/the-trip-2017/enter

Win a Trip for 2 to Jamaica

by Travel Sweepstakes Blogger on December 30, 2016

Hang out on the islands! Enter this sweepstakes for a chance to win a trip for two to Jamaica. The prize includes $500 for airfare, five nights at the all-inclusive Meliá Braco Village and a Hamptons Lane Festive Baking box. Deadline: Jan. 10, 2017. https://hamptonslane.com/sweepstakes/jamaica

 

Win a Trip for 2 to Saint Lucia

by Travel Sweepstakes Blogger on December 22, 2016

Unwind in the tropics! Enter this sweepstakes for a chance to win a trip for two to Saint Lucia. The prize includes $1,5000 for airfare, plus five nights at Hotel Garce Bay, as well as a $500 Shoptiques.com gift card. Deadline: Dec. 31, 2016. http://www.shoptiques.com/giveaway

Win a Trip for 2 to Antigua and Barbuda

by Travel Sweepstakes Blogger on December 7, 2016

Hit the tropics! Enter this sweepstakes for a chance to win a trip for two to Sandals Grande, Antigua Resort. The prize includes round trip air, three nights lodging and more. Deadline: Dec. 15, 2016. http://visitantiguabarbuda.us/sweepstakes/

Win a Trip for 2 to Belize

by Travel Sweepstakes Blogger on November 28, 2016

See paradise. Enter this sweepstakes for a chance to win a trip for two to Belize that includes roundtrip air from Houston, four nights at El Pescador Resort, three meals a day, select beverages, plus a choice of El Pescador ECO Adventures. Deadline: Dec. 29, 2016. http://www.orvis.com/holidaysweeps

 

Win a Trip for 2 to Aruba

by Travel Sweepstakes Blogger on November 25, 2016

Hit the tropics! Enter this sweepstakes for a chance to win a trip for two to Aruba. The prize includes round trip air, four nights lodging, and a guided local tour. Deadline: Nov. 30, 2016. http://www.aruba.com/local-shortcuts-sweepstakes