10 Cheap Caribbean Destinations to Visit in Winter 2019

Freezing temps, fewer daylight hours, and post-holiday blues -- there’s enough to put you in a slump this time of year. Avoid all of that with a cheap Caribbean vacation this winter. Using Oyster-specific data from last winter (December 2017 through March 2018), we found the average hotel price per night in various Caribbean locales. We also took into account things like airfare (mostly from major city airports) as well as food and entertainment prices. From Martinique to Guadeloupe, these 10 Caribbean destinations offer a nice, warm respite on the cheap.

Dominican Republic

A beautiful natural landscape, warm weather and even warmer locals, a rich history, convenient flights, and wallet-friendly prices are just a few of the reasons to escape to the Dominican Republic this winter. The country is home to a large selection of all-inclusive resorts, especially in places like Punta Cana and Puerto Plata, so value-oriented visitors can save by booking hotels where everything (food, liquor, activities) is included. Punta Cana also offers affordable zip-lining, windsurfing, kayaking, and golfing. Plus, with eight international airports on the island, this destination is not only inexpensive, but also easy to reach.

Our Hotel Pick: Majestic Colonial Punta Cana

The Majestic Colonial Punta Cana is one of three upscale all-inclusive sister properties on a beautiful stretch of Bavaro Beach. The property closed completely for two months in 2017 to thoroughly renovate the lobby and restaurants. It now operates almost as two resorts: the family-friendly side and the adult-only Colonial Club side. The 658 suites are attractive with marble floors, jetted tubs, and some ocean views.


Oceanfront Pool at The Scuba Lodge & Suites, Curacao/Oyster

Come for the relatively inexpensive hotel rates, stay for the near-perfect weather. Situated off the north coast of Venezuela, this Dutch Caribbean island is somewhat of a hidden gem, lacking that overrun touristy feel of other Caribbean destinations. But it does boast a big airport, which means more frequent and less-expensive flights. The postcard-perfect beaches make it a popular spot for scuba divers, while the capital, Willemstad, features photogenic colonial architecture, the floating Queen Emma Bridge, and other cultural attractions.

Our Hotel Pick: Van Der Valk Kontiki Beach Resort

The upper-mid-range Kontiki Beach Resort aims to create the feeling of a tropical paradise, and generally succeeds; lush green foliage surrounds its four romantic lagoon-style pools and the 80 modern rooms, constructed in dark wood from Brazil, feel tucked away in the jungle. The vibe is young and trendy, especially at the Cabana Beach restaurant and beach club next door, where some nights the party goes into the wee hours.

St. Martin/St. Maarten

Split between the French and Dutch, St. Martin and St. Maarten have distinctly different governments, languages, cuisine, currencies, and overall vibes. In other words, you’ll know when you’ve crossed the border — even though there isn’t a strict one. But even with their differences, the two find common ground — both sides boast excellent beaches with crystal clear waters. When booking a vacation on a budget, opt for staying on the Dutch side. Not only do more flights frequent this area, but it’s also cheaper. Here, visitors will find large, all-inclusive resorts packed with entertainment, as opposed the more secluded, intimate accommodations on the French side. Bonus: Sint Maarten’s capital of Philipsburg has great shopping and lively nightlife.

Our Hotel Pick: Belmond La Samanna

Easily the most luxurious resort in St. Martin, the 55-acre La Samanna resort brings tranquility to an otherwise tourist-filled island. Featuring two beautiful pools, an extensive wine cellar, a yoga and Pilates studio, a European-style spa, and the island’s most pristine beach, this 81-room, eight-villa retreat is hard to beat.


If you’re the type of traveler who likes to relax on a beach one day, then do something adventurous like hike in the rainforest the next, consider Martinique, a Caribbean island that’s part of the Lesser Antilles. While there, don’t miss Mont Pelée, a semi-active volcano that towers over the town of Saint-Pierre. The French-speaking island’s diversity extends beyond its landscapes, and it’s also home to a slew of land and sea activities. The local dining scene, which is packed with Creole and Caribbean flavors, live music, and stylish French fashion all make this year-round tropical destination worth a visit. Head to Fort-de-France, the capital city, for the stores, restaurants, clubs, and other attractions. But even with these features, Martinique remains a little off the beaten (tourist) path, which means fewer crowds. And while it has its fair share of luxury resorts and villas, the island also comes with plenty of budget-friendly options.

Our Hotel Pick: Club Med Buccaneer’s Creek

On an island beset with small, mid-range properties, Club Med Buccaneer’s Creek stands out for its size alone. The large, three-pearl all-inclusive offers a wide-range of amenities including one of Martinique’s longest hotel beaches, a beautiful, oceanfront infinity pool, and two open-air restaurants with excellent food.


An archipelago of islands, Guadeloupe (also known as the “Butterfly Island”) is endowed with physical beauty that ranges from beautiful beaches to looming volcanoes. To the east, you have Grande-Terre, which is known for its silky white sand, teal waters, and sports like snorkeling and diving. To the west lies Basse-Terre, which is home to Guadeloupe National Park and the active La Soufriere volcano. The exotic locale, which blends French and Caribbean culture, also comes with many bang-for-your-buck hotels.

Our Hotel Pick: La Toubana Hotel & Spa

This 44-room, 121-acre hotel is the top upscale option on Guadeloupe. It dominates the side of a mountain and descends gradually down to the ocean, leading to its own tiny but essentially private beach cove, complete with a long pier and platform-topped boulder. Meanwhile, up on top, an infinity pool offers a stunning view of waves crashing against a handsome cliffside. It’s a dream Caribbean setting, and the rustic-luxe bungalows have enormous terraces, many with terrific ocean views.

Trinidad and Tobago

Situated off the coast of Venezuela, the small country of Trinidad and Tobago comprises two islands. Trinidad is the larger, more industrialized island of the two, while Tobago is smaller and much more popular among tourists. The latter also offers nature reserves and beaches plus ample opportunities to go bird-watching and diving. What Trinidad lacks in beaches, it helps compensate for in historical attractions like the Magnificent Seven, a row of beautiful mansions. And while the country doesn’t have extensive lodging options (in Tobago, there are small and charming beachfront boutiques, plus a couple of all-inclusive options), the price is — more often than not — right. The daily direct flights to Trinidad from major airports like JFK in New York City don’t hurt either.

Our Hotel Pick: The Villas at Stonehaven

While it lacks convenient beach access, the four-pearl The Villas at Stonehaven offers a small, but stunning infinity pool and a poolside restaurant. The 14 stand-alone villas are among the most upscale and feature-rich accommodations in Tobago. They include full gourmet kitchens, personal housekeepers, and private pool terraces with stunning views.

Puerto Rico

In Puerto Rico, huge malls, golf courses, and casinos share the skyline with tropical rainforests, beautiful white-sand beaches, colorful colonial buildings, and well-preserved 15th-century Spanish forts. That means no matter what you fancy — a quiet retreat or a party destination — you’ll find it on this Caribbean island. Plus, since it’s an unincorporated U.S. territory, U.S. visitors need not worry about the hassles that come along with international travel. And while all-inclusive resorts are scarce, inexpensive hotels aren’t tough to come by.

Our Hotel Pick: San Juan Marriott Resort & Stellaris Casino

San Juan Marriott Resort & Stellaris Casino is an upmarket, four-pearl resort located in San Juan’s chic Condado neighborhood. The resort’s 525 guest rooms are tasteful if somewhat chain-like, with all offering private balconies with city, pool, or ocean views. There are lots of on-site amenities, including a pair of lovely pools, five diverse dining options, ample meeting space, as well as a solid spa and fitness center.


Home to beautiful beaches, a lively nightlife scene, and flavorful food, Jamaica has long been a popular Caribbean destination. The island nation is also home to many all-inclusive resorts, meaning visitors can find inexpensive accommodations 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.

Our Hotel Pick: Grand Palladium Jamaica Resort & Spa

Located 45-minutes west of Montego Bay, Grand Palladium Jamaica Resort and Spa feels a world away from anywhere. Even compared to the island’s typical large hotel complexes, the three-and-a-half-pearl mega-resort is massive. With an 86,000-square-foot pool complex, ten restaurants, late-night entertainment, and eight bars with nearly 24-hour drinking opportunities, it’s easy to imagine that most guests will never leave the property.


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.

Our Hotel Pick: Waves Hotel & Spa by Elegant Hotels

With competitive pricing, lovely rooms, and great on-site amenities, this 70-room boutique hotel will attract people who never thought they’d choose an all-inclusive package. With three restaurants, cabanas on the terrace, and a late-night lounge, Waves has a contemporary appeal especially for couples (though families aren’t overlooked). Spacious rooms are modern and bright, and most have glass-balconies (oceanfront rooms are worth the cost for the sunsets alone).

U.S. Virgin Islands

If you avoid the major ports where cruise ships dock, you can often find a solid deal on a hotel in the U.S. Virgin Islands, where the three main islands are St. Croix, St. John, and St. Thomas — or you can choose 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.

Our Hotel Pick: The Westin St. John Resort Villas

he four-pearl Westin St. John Resort Villas is the largest resort on tiny St. John. The decor is typical of the Westin brand, with meticulous landscaping and modern, upscale interiors. Features include a soft sand beach, a large pool, two beachfront restaurants, and a full-service spa and salon.

What to Bring: Sunscreen

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