The Best Cheap Caribbean Holidays 2019 – We Compare Providers Of All Inclusive Vacation Packages!

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Dreaming about long stretches of beautiful white sand beaches, palm trees and gentle breezes? Who isn’t! But if you’re actually looking to take a trip with your family this summer, you’ve come to the right place. We’ve compiled a list of the best deals on the web to make choosing where to spend a vacation in the Caribbean easy.

Using popular tourist destinations Jamaica and Barbados, we compared prices using the following details:

  • Traveling for 7-days.
  • The trip will be all-inclusive.
  • It will be a family of 4 going, that’s 2 adults and 2 kids under 10 years of age.


All the deals below feature at the very least a flight and hotel, and we’ve ranked them from most expensive to cheapest. That said, considering what you get in each, they’re all great deals in their own right.

So, let’s get into it. First we’ll look at the best all inclusive deals to Jamaica, then we’ll we’ll show the top bargains to Barbados. A couple of things to bare in mind when looking at these deals:

Note: All numbers are correct at the time of writing this, but please do a search on the mentioned websites to compare their latest deals and prices. Details can fluctuate wildly based on the time of year you want to travel, how full up the flight or accommodation is, how close to the flight date you’re booking, and many other factors.

Note 2: Please do your own research in terms of the quality of each stay and if they’d match your personal needs. In this article we’re looking for the cheapest holidays to Jamaica online, although we’ve still listed the most expensive as they may offer better value for money in terms of features.

The Best Cheap Jamaican Holidays

Cheap vacation packages to Jamaica all inclusiveSo let’s start off with great all inclusive packages to Jamaica, highest price to lowest. Some of the earlier ones are luxury, so skip towards the end for the lower cost options.

7. Strawberry Hill Hotel

The Strawberry Hill Hotel In Jamaica

Image source: Luxury Dream Hotels

  • $1136 per person.
  • Deal from JetBlue.

This hotel sits high on a hill overlooking Kingston, with an infinity pool that offers beautiful views of the city and harbour, so you and your family will be left wanting for nothing in the wonderfully renovated, Georgian-style hotel. Because the hotel is small – it only has 13 units – you know you’re going to get personalized service, which makes up for the slightly higher price tag. This hotel is also a little further away from the popular sights of Kingston and the airport, but the views are unbeatable.

6. Hilton Rose Hall Montego Bay

The Hilton Rose Hall Montego Bay - A High End Hotel

This all-inclusive package promises a wonderful and relaxing stay in beautiful Montego Bay, and the lush Hilton Rose Hall is sure to satisfy all your family’s needs. With its own private beach, the hotel is a paradise on a 400-acre site that used to be a sugar plantation in the 1800s and it has its own water park. It’s also only five miles from the
airport, so getting to and from the hotel is no hassle at all. It has one of the highest guest ratings we’ve seen on the web, so even though the price is the second highest one on this list you’re still guaranteed to get what you pay for.

5. Sunscape Splash Montego Bay

Part hotel, part water park, this hotel will be sure to delight both parents and kids alike. It’s a little more expensive than some of the other deals we’re featuring here but for what you get it’s totally worth it. The package is all-inclusive, so once you get to the hotel everything is paid for and all you have to do is sit back and relax. Montego Bay is famous for its resorts, and since it’s a popular cruise ship port, there are plenty of fun touristy things to do if you want to venture away from the hotel. Apple Vacations reviewers give the hotel four stars (well, they’re apples, but it’s the same thing), so you won’t be disappointed.

4. Riu Negril Hotel

  • $832 per person.
  • From FunJet.

All-inclusive meals are a big plus at this Jamaican hotel, but there are plenty of other perks that make it worth the few extra miles it takes to get there from the airport. The Riu Negril is a five-star hotel, so you know there will be no expense spared to make your family’s stay as relaxing and enjoyable as possible. The hotel is also only 3.5 kilometres away from the Kool Runnings Waterpark which has 4.4 stars on Google reviews, so you know the kids will be entertained for hours if you make the trip there. Of course, the hotel has its own pool and recreational activities for kids onsite, like kayaking and movie projections as well as a play area.

3. Courtyard by Marriott Kingston

  • $788 per person.
  • Book via Expedia.

The best package deal we found for Jamaica on Expedia was the Kingston Marriott at $788, which includes a non-stop flight if you’re leaving from Miami, Florida. Marriott hotels are known for being reliable, and the reviews for the one in Kingston express similar views. Speaking of views, this hotel is right on the beautiful boardwalk in Jamaica’s capital city, so there’s plenty to see out the windows of the hotel. The beach is a little bit of a trek, but that’s the trade-off for the great price and downtown location.

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