What is the best time to find a cheap Caribbean holiday?

You're spoilt for choice when it comes to the Caribbean. With over 28 nations to choose from and over 7,000 islands to explore, you can soak up the sun in ways you didn't think were possible.

Many islands have European history and cultural influences, and some are even still owned and maintained by European nations, but which one is right for you? For those hoping to offset the cost of flights on land, read the following guide:

Generally speaking, the best time to find a cheap Caribbean holiday is during the low season, which runs from mid-April to mid-December. However, the best months to go are arguably between June-August.

Throughout August, flights are cheap, as well as hotels and vacation homes. If you're seeking a cruise or an all-inclusive resort package, the winter months of October, November and mid-December are your best shot at landing the best deal.

Which islands are the cheapest to visit?

  • Cancun (Mexico)
  • Puerto Plata (Dominican Republic)
  • Varadero (Cuba)
  • Rincon (Puerto Rico)
  • Montego Bay (Jamaica)

Cheap places to stay in the Caribbean

When booking for a holiday in the Caribbean, you might find a lack of options on sites like Airbnb or even hostels. Instead, you have hotels and vacation homes to choose from. Splurge a little more on an all-inclusive holiday package and you can have everything from drinks to food, to even activities paid for in advance.

To keep costs low, you'll always want to buy travel insurance. Ensure that you're covered for all the activities you want to get up to so that there aren't any additional expenses you need to worry about in case of any emergencies.

Related content

If you enjoyed this article and would like more info on travel to Tunisia, check out our other posts on the topic.

Holiday Extras Cover Limited are authorised and regulated by the Financial Conduct Authority under registration number 828848, Holiday Extras Cover Ltd 05058680 is registered in England and Wales. Registered address, Ashford road, Newingreen, Kent CT21 4JF

Holiday Extras Cover Ltd is underwritten by White Horse Insurance Ireland dac is registered in Ireland No. 306045. White Horse Insurance Ireland dac’s Registered Office is First Floor, Rineanna House, Shannon Free Zone, Shannon, County Clare, Republic of Ireland. White Horse Insurance Ireland dac is authorised and regulated by the Central Bank of Ireland. Deemed authorised by the Prudential Regulation Authority and subject to regulation by the Financial Conduct Authority and limited regulation by the Prudential Regulation Authority. The nature and extent of consumer protections may differ from those for firms based in the UK. Details of the Temporary Permissions Regime, which allows EEA-based firms to operate in the UK for a limited period while seeking full authorisation, are available on the Financial Conduct Authority’s website, our FRN is 203320.