The 10 Cheapest Caribbean Destinations to Visit This Winter, Ranked

Split between the French and the Dutch, but with no real boundary marks, St. Martin and Sint Maarten each have different governments, languages, cuisine, currencies, and attitudes in general. Although there isn't a strict border, once you've crossed over into the other country's land, you'll soon know it -- and if you're booking a vacation on the cheap, we'd recommend staying on the Dutch side. Not only do most flights land here, but it's also a tad cheaper to stay in this area as well. Plus, Sint Maarten's capital of Philipsburg has great shopping, a lively nightlife, and a beautiful waterfront boardwalk for viewing the sunset.


Where to Stay: Holland House Beach Hotel

The Bahamas is one of the easiest Caribbean destinations to reach from the US; it's close by, and daily flights land at the two island airports from most major East Coast cities. Add in the convenience of not needing to switch currency (the Bahamian dollar is pegged to the US dollar), year-round pleasant weather, world-class golf courses, great waters for scuba diving and snorkeling, and delicious (cheap) local eats like conch and grouper, and you've got a prime getaway for this winter.


Where to Stay: Paradise Cove Beach Resort

While flights to Martinique may not always be the cheapest Caribbean options, the French-speaking island is home to a variety of budget-friendly hotels, and it lacks the uber-touristy feel that some islands carry. The tropical climate here makes for balmy winter weather, and visitors often come not only for the beaches but also for the rain forests. Local dining focuses on a delicious blend of Caribbean and Creole flavors.


Where to Stay: Residence Oceane Hotel

At first glance, it might be easy to view the white and pink sand beaches and breathtaking coral reefs of Barbados as a clichéd Caribbean island experience, but there's more to it than that. The island has developed quickly from an impoverished sugar based economy to a democracy with one of the highest literacy rates in the Western Hemisphere. Despite these impressive changes, the friendly locals (known as Bajans) maintain a noticeable amount of British customs from their colonial past, such as afternoon tea time and driving on the left -- but don't worry, an extensive bus system makes it easy (and inexpensive) to get around. Barbados also stands out from other Caribbean islands with the diverse set of visitors it attracts, ranging from budget travelers to luxury vacationers. The calm luxurious beaches of the west coast attract the majority of tourists, but the windswept east coast attracts a fair share as well, with surfer-friendly shores facing the Atlantic.


Where to Stay: White Sand Beach Villas

If you avoid the major ports where cruise ships dock, you can often find a solid deal on a hotel in the US Virgin Islands, where the three main islands are St. Croix, St. John, and St. Thomas -- or you can opt to go super-budget and camp on the beaches of smaller islands, such as Water Island. As they have for the past 400 years (back all the way to the time of the pirates of yore), people come to these islands mainly to drink, relax on the beach, and bargain shop -- often, in just that order.


Where to Stay: Virgin Islands Campground

One of the Caribbean's hidden gems, Grenada is often overlooked; we advise against this. Because this small island towards the southernmost end of the Caribbean island chain is home to beautiful white-sand beaches set against volcanic views. While flights here are relatively budget-friendly year-round, you'll find the best hotel deals during the early winter -- and better yet, fewer crowds too.


Where to Stay: The Flamboyant Hotel & Villas

Home to tons of all-inclusive resorts, the Dominican Republic is a solid pick when planning a wallet-friendly Caribbean getaway; visitors can save by relying on hotels where everything -- from activities to food, from entertainment to alcohol -- is included, and with eight international airports on the island, it is often quite easy (and inexpensive) to reach. Add in lovely beaches, warm locals, great year-round weather, and a rich history for a wonderful winter getaway.


Where to Stay: The Tropical at Lifestyle Holidays Vacation Resort

Another Caribbean island that often isn't one of the first to come to mind, Curacao is a favorite among scuba divers -- and those looking to take an inexpensive vacation; hotel rates are best in November, but can stay relatively low throughout the winter as well, particularly when compared to other Caribbean islands towards the southern end of the chain. Plus, it has a large airport which means more frequent, and less expensive, flights. If you seek a Dutch-Caribbean vibe similar to the one found in Sint Maarten (but perhaps a bit less built-up), Curacao is a great option.


Where to Stay: The Scuba Lodge & Suites

Jamaica has long been a popular Caribbean destination -- home to friendly locals, lovely beaches, and a lively nightlife (where reggae, of course, takes center stage). Many credit the island as the birthplace of the all-inclusive resort, which means visitors can find plenty of inexpensive lodging at massive, all-expenses-pre-paid hotels, particularly in Montego Bay. This region is also a solid choice for budget travelers because it is where you can find Jamaica's busiest airport. However, Negril is another wallet-friendly option, and most would argue that the beaches here (Seven-Mile Beach especially) are more beautiful.


Where to Stay: Negril Tree House Resort

And now for the winner! It is no secret that Puerto Rico is one of the cheapest options for US travelers heading to the Caribbean, but we say it is the cheapest. And thankfully, we find the island -- just about 1,000 miles from Florida -- to be absolutely beautiful, too. Since it's an unincorporated US territory, US visitors need not worry about international travel, which takes out the hassle of finding your passport and the expense of a non-domestic flight. All-inclusive resorts are rare, but inexpensive hotels are an easy enough find. Plus, visitors have beautiful beaches, bioluminescent bays, delicious seafood, great shopping, and adorable historic areas to look forward to.


Where to Stay: Villa Montana Beach Resort


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