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Caribbean

The Caribbean offers a variety of islands each with stunning beaches, laid-back vibes, and plenty of things to do and see. Here you'll find our cheap deals on flights, hotels, vacations, and cruises to the Caribbean. Check back if you're looking to chill out in Jamaica, go diving off the coast of Dominican Republic, leave your passport behind for a trip to Puerto Rico or the U.S. Virgin Islands.

Show deal: Adults-Only & All-Inclusive: Punta Cana Trip From $495 With 4-Star Beach Resort

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Vacations

Pirates, we've found a great deal on one of the best resorts in Punta Cana, Dominican Republic. You'll save close to 15% when you book a 3-night vacation to this highly-rated adults-only and all-inclusive property. Deal Overview Accommodations: 4-star Barcelo Bavaro Beach (4.5/5 on TripAdvisor) Meals & Drinks: All-inclusive Airline(s): Determined at time of booking…

Show deal: Fly To St. Thomas, USVI From $135 Round Trip—Reg. $600+!

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Flights

Pirates, a great suggestion for a sunny getaway destination would be the US Virgin Island St. Thomas—no visa or passport required! Flights are currently available for just $135 round trip, as cheap as it can get! Flight Overview Airline(s): Spirit, American Airlines Baggage Info: Please visit our baggage information post for more details Travel Document:…

Show deal: 7-Night Disney Cruise From $1441—Sail Out Of Texas

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Cruises

Pirates, grab this rare deal on a Disney cruise to the Bahamas leaving from Galveston, Texas (right outside of Houston). You'll head to Key West, Nassau, and Disney's private island, Castaway Cay, and celebrate savings of $100 or more per person! The advertised price includes taxes & fees. You will have to pay onboard gratuities…

Expired: Great Deal: 10 Western US Cities → Barbados From $366 Round Trip! (Reg. $575+)

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Flights
Expired

Western US pirates, book these cheap round-trip flights to breathtaking Bridgetown, Barbados! Enjoy this island's stunning Caribbean beaches, tropical weather, and delicious rum. These are the lowest prices we've seen lately and these flights normally cost over $575, so book today to save big. Flight Overview Airline(s): jetBlue, American, Spirit, Copa Baggage Info: Please visit…

Expired: Dominican Republic 5-Night All-Inclusive Vacation From $512—Incl. Flights & Junior Suite

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Vacations
Expired

Pirates, head for the beautiful beaches of the Dominican Republic with this great value vacation! From just $512 you can spend five nights living it up in a junior suite at this gorgeous beachfront all-inclusive resort, with round-trip flights included. Hurry, these great prices won't last long! Deal Overview Accommodations: 3.5-star Grand Bahia Principe La…

Expired: All-Inclusive 5-Night Jamaica Getaway From $579: Holiday Inn Beach Resort & Flights

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Vacations
Expired

Pirates, looking to escape the cold with an all-inclusive Caribbean getaway? Head down to Montego Bay, Jamaica this fall or winter for a worry-free 5-night vacation. With one easy click you can book your stay at a well-rated Holiday Inn Sunspree beach resort and round-trip flights—all for a bargain. Deal Overview Accommodations: 3.5-star Holiday Inn…

Expired: Northeast To Barbados From $268 Round Trip—Reg. $450+!

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Flights
Expired

Northeast pirates, book these cheap round-trip flights to breathtaking Bridgetown, Barbados! Enjoy this island's stunning Caribbean beaches, tropical weather, and delicious rum. Flight Overview Airlines: American, jetBlue Baggage Info: Please visit our baggage information post for more details Travel Document: Valid passport Visa Required For U.S. Citizens? No Please keep in mind that flights are…

Expired: Northeast → Aruba From $252 Round Trip (Reg. $350+)

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Flights
Expired

Northeast pirates, start packing your swimsuits and sunscreen because you're going to beautiful Oranjestad, Aruba for an incredible price! Hit the beach, go kayaking, or head out on a snorkeling adventure—this island has it all. Hurry up and book your tickets because these are the lowest fares we've seen recently. Flight Overview Airlines: jetBlue, Spirit,…

Expired: Budget All-Inclusive Riviera Maya Getaway From $367

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Vacations
Expired

Pirates, looking for an affordable all-inclusive getaway to Mexico's stunning Riviera Maya? Spend three nights at a beachfront resort with round-trip flights included from only $367! With dates from September through October from both coasts, there's plenty of availability for a last-minute escape to the Caribbean. Similar trips can cost $700+, so act fast to…

Expired: Aruba 4-Night Getaway From $456—49% Off!

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Vacations
Expired

Pirates, head to sunny Aruba this fall and winter, with this affordable 4-star vacation from $456 for flights and 4-star resort! Aruba is home to stunning white sand beaches, year-round warm weather, and iconic wild flamingoes—do you need more reasons to go? Deal Overview Accommodations: 4-Star Holiday Inn Resort Aruba (4/5 on TripAdvisor) Airline(s): Determined…

Expired: Philadelphia → San Juan, Puerto Rico From $97 Round Trip (Reg. $450+)

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Flights
Expired

Philadelphia pirates, we've found incredibly cheap nonstop flights to San Juan. With gorgeous beaches, delicious food, and a rich culture, Puerto Rico is the perfect passport-free Caribbean getaway. These are the lowest prices we've seen from Philly all year, so don't wait to score these tickets for a fantastic price! Flight Overview Airline(s): Frontier Baggage…