Cheap Caribbean Vacations

CheapCaribbean is a US-based online travel aggregator for Caribbean and Mexico vacation packages, all-inclusive resorts and cruises, so pick your package, then book through ShopBack before you pay: ShopBack Cashback works like a discount, only easier than a promo code. It bundles airfare, hotel, and transfers into single-price packages sold direct to consumers. Book via cheapcaribbean.com and activate ShopBack via the ShopBack CheapCaribbean merchant page to earn cashback on eligible bookings at the current published rate.

CheapCaribbean does not operate a standalone loyalty programme. As an aggregator, points and elite credit accrue through the underlying hotel brand (Marriott Bonvoy, Hilton Honors, World of Hyatt, ALL Accor) or airline programme (Delta, American, JetBlue, Southwest) tied to your booking, provided the fare is a scheduled carrier ticket and the property recognises third-party OTA stays for points. Check per property, since some Marriott and Hilton programmes exclude OTA bookings from elite credit. To earn Cashback on the booking, start from the CheapCaribbean page on ShopBack before you pay.

CheapCaribbean runs promo windows around Black Friday (November 27, 2026) and Cyber Monday (November 30, 2026) with sitewide savings codes on packages that include hotel and air. Additional windows include Memorial Day (May 25, 2026), Fourth of July, Labor Day (September 7, 2026), and Wave Season (January to March). Prior years have run BFCM promos with $500 sitewide savings and Summer 2026 offered a $200 promo code for hotel-plus-air bookings with a 4-night minimum. Verify current codes and eligibility on cheapcaribbean.com before booking.

CheapCaribbean packages a single price from an airline seat plus a resort night contract negotiated directly with the property or through a wholesale supplier. The all-in price often prices below the sum of separately-booked components, especially at branded all-inclusive resorts (Sandals, Iberostar, Riu, Barcelo, Palladium, Hard Rock, RIU). Air is ticketed as a scheduled carrier flight (Delta, American, United, JetBlue, Frontier, Spirit, Southwest depending on route), so airline mileage typically posts. Transfers may be included or sold as an add-on depending on the destination.

CheapCaribbean typically ticketed as scheduled carrier flights across all major US departure cities, which gives more schedule flexibility and airline mileage earning across Delta, American, United, JetBlue, Southwest, Frontier, and Spirit. Apple Vacations bundles charter flights into many packages out of Northeast and Mid-Atlantic hubs, which often produces the lowest total package price on Cancun and Punta Cana for those specific routings. For flexible dates or non-major-hub departures, CheapCaribbean often has broader inventory. For fixed-date charter routings out of EWR, BOS, or PHL, Apple often wins on total price. Cross-check both. Both are cashback-eligible via ShopBack where applicable.

Expedia has broader global inventory, including Europe, Asia, and domestic US, plus stronger Marriott and Hilton brand coverage on hotel-only bookings, and its own points programme (One Key). CheapCaribbean is narrower but often deeper on Caribbean and Mexico all-inclusive resort inventory (Sandals, Beaches, Riu, Iberostar, Barcelo, Palladium, Hard Rock) with negotiated package pricing that can undercut Expedia on identical resort and dates. For a Caribbean or Mexico all-inclusive, CheapCaribbean is worth checking first. For any other destination or a hotel-only booking, Expedia wins on breadth. Both are cashback-eligible via ShopBack where applicable. For a deeper look, see Hawaii vs Mexico vs Caribbean 2026.

True all-inclusive resorts (Sandals, Beaches, Riu, Iberostar, Barcelo, Palladium, Hard Rock, RIU) bundle meals, drinks, non-motorised watersports, entertainment, and standard gratuities into the package price with no separate mandatory resort fee. Some non-all-inclusive Caribbean and Mexico properties (Miami, Fort Lauderdale, non-inclusive Riviera Maya hotels) do charge a nightly resort fee in addition to the package price, payable at check-out. Check at booking. Motorised watersports, spa, premium dining, and off-property excursions are typically not included even at true all-inclusive resorts.

CheapCaribbean ticketed as scheduled carrier flights on Delta, American, United, JetBlue, Southwest, Frontier, and Spirit, giving effective coverage from any major US metro. Miami (MIA), Fort Lauderdale (FLL), New York (JFK, EWR, LGA), Atlanta (ATL), Charlotte (CLT), Dallas (DFW), Chicago (ORD), and Houston (IAH) typically offer the lowest package prices to Cancun, Punta Cana, Montego Bay, Nassau, and Aruba because of nonstop routing. Secondary metros ticket with one connection at slightly higher package cost. Verify routing at booking.

Open the ShopBack CheapCaribbean merchant page, continue to cheapcaribbean.com and complete the booking there, then keep the reservation email. Go through ShopBack before you pay and the Cashback tracks to your ShopBack account. Rates and eligible booking types vary, and the CheapCaribbean page on ShopBack shows the live rate.

Yes. That includes bookings cancelled within the free-cancellation window and trips that do not depart.

CheapCaribbean Vacations announces its own public promo, sale and member codes. ShopBack Cashback works like a discount, only easier than a promo code: go through ShopBack before you pay.

CheapCaribbean does not operate a native booking app, so you book at cheapcaribbean.com in a mobile or desktop web browser. On your phone, open CheapCaribbean from the ShopBack app and finish the booking there.

ShopBack's guide on Cheap Caribbean Vacations covers affordable sunny holiday spots: What Is the Cheapest Tropical Place to Vacation From the US in 2026?.