10 Most Affordable Caribbean Destinations This Winter

Because many of the cultural destinations in Europe are inside, it's the perfect place to visit in the cooler months. 'I would consider Old World cities like Paris, Amsterdam, and Berlin,' says Willdorf. 'Hotel prices are much lower, and most activities would be indoors anyway.' Here are 15 places you need to go in 2019.
Finding a cruise that's both affordable and romantic is no easy feat. The most romantic cruises are typically offered by pricey luxury lines (Think: Azamara, Regent, and Oceania) with outrageous amenities or on smaller cruise ships with far fewer passengers. At the other end of the spectrum are cruise companies catering to families and budget travelers. For couples seeking that sweet spot between romantic and affordable, here are a dozen options under $100 per night from midrange cruise companies that offer an opportunity to escape the crowds at least somewhat and enjoy some quality one-on-one-time.   All prices are subject to change and were researched in mid-January.
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Slide 2 of 21: $97 per night averageDominica, while small, is unique among the many Caribbean islands for its mountainous terrain, lush rainforests, and many natural hot springs. It’s also home to a volcanically-heated lake called Boiling Lake. This island is an especially wonderful option for adventurous travelers who love long hikes to remote scenic spots that make every uphill climb worth the effort.
Slide 3 of 21: Related: Here's How You Can Travel Back to Dominica After Hurricane Maria
Stay here: Make childhood dreams come true by staying in a real-life treehouse on the island of Dominica. Tucked amid rolling hills and lush forest, this eco-cottage is kept cool by sea breezes and sports breathtaking views. In addition to the two-bedroom cottage, you have access to the property’s hammock grotto, fire pit, and pergola. If you’re bringing a crew, a second cottage is nearby. Rates from $109 per night.
Slide 4 of 21: $108 per night average One island south of Dominica is rugged but delightful Martinique. This French Caribbean island perfectly blends West Indies culture and traditions with European influences. Steep hills and dense forests are broken up by cosmopolitan villages and sweet little towns of narrow streets, shops, and cafes. Come to Martinique for the bargains, and stay for the vast array of activities, beaches, hikes, and cultural opportunities.
Slide 5 of 21: Stay here: Situated along the calm waters of the Bay of Anse Mitan, this two-bedroom house is within walking distance of restaurants and markets in the tourist hotspot Les Trois-Îlets. The bay is great for yacht-watching and snorkeling, so everything you could possibly want from a relaxing vacation is right outside this quaint, quiet home. Rates from $123 per night.
Slide 6 of 21: $114 per night average In the Leeward Islands, petite Montserrat, a British Overseas Territory, is a melting pot of Caribbean and European cultures and traditions. The island’s active volcano Soufrière Hills, which last erupted in the 1990s, gives the island its signature black sand beaches—but it also makes the lower two-thirds of the island a generally off-limits “exclusion zone.” The north of the island, however, is home to stunning coral reefs and shoreline caves, perfect for eager explorers.
Slide 7 of 21: Stay here: Take in stunning sunsets from the porch of this Old Town cottage, lacquered in shades of blue that echo the seas and skies of the Caribbean. Breezes off the bay keep you cool and relaxed. Be sure to rent a car so you can hop into town or take a day trip to the north of the island. Rates from $64 per night.
Slide 8 of 21: $123 per night average Just off the northeast coast of Venezuela sits the dual island nation of Trinidad and Tobago. Known for its raucous Carnival and distinctive Creole cuisine, these Caribbean islands feature white sand beaches, dense mangroves, and lush rainforests. The republic is prized among bird watchers and divers alike, and the smallest island, Tobago, is renowned for its pristine beaches.
Slide 9 of 21: Stay here: This two-bedroom cabin sits above Erasmus Cove, on the northeast coast of Tobago. Your views are of tropical gardens, rainforest, and Bloody Bay below. You’ll be tucked away from the bustle of the island, but you’re close to town if you need to shop or grab a bite to eat. You also have access to secluded beaches so you can really feel like you’ve escaped the world. Rates from $140 per night.
Slide 10 of 21: $126 per night average Curaçao is part of the Dutch Antilles, a collection of Caribbean islands just a few dozen miles off the northwest coast of Venezuela. This petite island is prized for its incredible diving and snorkeling sites, but it’s a rising star in the Caribbean culinary world, too. The capital, Willemstad, is vibrant and colorful, with Colonial-era buildings that are vaguely reminiscent of the row homes of Amsterdam.
Slide 11 of 21: Stay here: If you want to stay in the vibrant capital, this Willemstad apartment will call to you. Rates start at $85 per night. But if it’s quiet (and ocean views) you seek in your Caribbean getaway, head for this Jan Kok villa (pictured), with its wrap-around portico for laidback sunset watching. Take advantage of the neighborhood’s amenities, including restaurants, bars, a wellness center, and pool. Walk to the nearby beach for a quick snorkel or swim, or hop into a car and explore the island’s dozens of snorkel and dive sites. Rates start at $115 per night.
Slide 12 of 21: $160 per night averagePuerto Rico is bouncing back as it rebuilds from Hurricane Maria’s devastation in the fall of 2017. The Caribbean island and unincorporated U.S. territory is priced right to draw tourists back to the country with flights as low as $115 dollars from some East Coast airports. Spend a day in Old San Juan and explore the island’s Spanish colonial buildings and fortresses. When you’re ready to relax, grab a spot on one of the pristine beaches or snorkel with sea turtles.
Slide 13 of 21: Stay here: Casita Fresca in Rincon is an island dream, with two bedrooms, an outdoor shower, and lush tropical surroundings that provide privacy. The west coast home, which is powered by solar energy, is a brief one-mile walk to the beach, or you can take a quick drive to many of the island’s other beautiful golden shores. You’re not far from downtown Rincon either, with its shops, restaurants, and beaches that are ideal for surfing. Rates start at $110 per night.
Slide 14 of 21: $193 per night average For eager hikers, the eastern Caribbean island of St. Lucia provides exquisite views from the Pitons, a pair of volcanic spiked mountains, which are also a World Heritage Site. If your vacation goals revolve around cucumber spa water, oversized sunglasses, and big hats, you’ll still find a lot to love, with St. Lucia’s luxurious beaches, waterfalls, and unparalleled vistas.
Slide 15 of 21: Stay here: In this Balinese-inspired cottage, you can perch yourself atop the tropical canopy and gaze at Rodney Bay and Pigeon Island for a vista like nowhere else on St. Lucia. The cottage is just a short walk from beaches, and a five-minute car ride to the village of Gros Islet. Rates start at $99 per night.
Slide 16 of 21: $199 per night average This boomerang-shaped Dutch Antilles island is quiet and humble compared to its sister islands, Aruba and Curacao, but don’t sleep on Bonaire. Divers and snorkel enthusiasts around the world know the beauty that lies just offshore this Caribbean island. The immense Washington Slagbaai National Park is home to wild donkeys and birds, and you’ll be sure to catch a glimpse of iguanas just about anywhere you go.
Slide 17 of 21: Stay here: Stay in the main town Kralendijk if you want to be close to restaurants and bars. If you don’t mind driving, set up outside the main drag for great prices and beautiful beachfront homes like this two-bedroom villa. This rental is beside Beyond the Corals, an excellent dive resort, and you’ll have access to their facilities if you stay here. The villa is surrounded by lush gardens and features a private pool so you can go for a dip after your day of diving, lounging, or snorkeling. Rates start at $129 per night.
Slide 18 of 21: $212 per night average Jamaica is renowned for its private all-inclusive resorts and lush, secret bays. All too often, however, those come with a hefty price tag. Jamaican bargains can be found if you know where to look. Seek out accommodations around Port Antonio, Ocho Rios, and Treasure Beach. These locations are laid-back but offer unique vibes that make this island so special.
Slide 19 of 21: Stay here: This Treasure Beach house captures the essence of Caribbean living, with its broad beach views, understated-but-elegant decor, and coastal breezes to keep you cool all day and night. A cook/housekeeper and live-in caretaker are also happy to show you around the grounds and introduce you to the many fruit trees and palms. Rates start at $150 per night.
Slide 20 of 21: $273 per night average This southern Caribbean island nation consists of a series of 32 smaller islands and cays, many of which are entirely off-the-grid of traditional Caribbean travel. Saint Vincent and the Grenadines provide safe harbor to many yachts and sailboats and acts as the home base to multiple private islands in this part of the sea. But away from the boats, the nation is also home to idyllic beaches and rugged, mountainous landscape.
Slide 21 of 21: Stay here: Union Island sits at the far southern end of the archipelago, and it’s the ideal location for adventurous travelers who don’t mind taking an uncharted path. The island is home to no major resorts but several low-key towns, which makes mixing and mingling with the locals natural. Make this Union Island house your home base for your stay in the Grenadines. You’ll be able to see nearby Mayreau Island and Tobago Cays, which you can hop to for the day via a ferry.

The Caribbean is exotic and unparalleled with its blue waters, sugar-sand beaches, and seemingly endless islands ripe for exploring. It’s a natural draw, too, for eager travelers looking for an escape during winter’s cold, gray days. Flights from East Coast hubs like Miami, Atlanta, and New York are bargain priced, with some fares as low as $200. (Departures from New York City and Atlanta to Puerto Rico are particularly good buys.) Despite its popularity in colder months, the Caribbean maintains much of its affordable pricing, and the islands have a wide range of accommodations, from five-star villas to quaint and cozy cottages tucked away in island hills. Many are incredibly affordable, even in peak season. Whether you’re looking to get away for a weekend or a long, relaxing week, look first to these Caribbean destinations, which Airbnb says are the most affordable this winter.

Dominica

$97 per night average
Dominica, while small, is unique among the many Caribbean islands for its mountainous terrain, lush rainforests, and many natural hot springs. It’s also home to a volcanically-heated lake called Boiling Lake. This island is an especially wonderful option for adventurous travelers who love long hikes to remote scenic spots that make every uphill climb worth the effort.

Related: Here’s How You Can Travel Back to Dominica After Hurricane Maria

Stay here: Make childhood dreams come true by staying in a real-life treehouse on the island of Dominica. Tucked amid rolling hills and lush forest, this eco-cottage is kept cool by sea breezes and sports breathtaking views. In addition to the two-bedroom cottage, you have access to the property’s hammock grotto, fire pit, and pergola. If you’re bringing a crew, a second cottage is nearby. Rates from $109 per night.

Martinique

$108 per night average
One island south of Dominica is rugged but delightful Martinique. This French Caribbean island perfectly blends West Indies culture and traditions with European influences. Steep hills and dense forests are broken up by cosmopolitan villages and sweet little towns of narrow streets, shops, and cafes. Come to Martinique for the bargains, and stay for the vast array of activities, beaches, hikes, and cultural opportunities.

Stay here: Situated along the calm waters of the Bay of Anse Mitan, this two-bedroom house is within walking distance of restaurants and markets in the tourist hotspot Les Trois-Îlets. The bay is great for yacht-watching and snorkeling, so everything you could possibly want from a relaxing vacation is right outside this quaint, quiet home. Rates from $123 per night.

Montserrat

$114 per night average
In the Leeward Islands, petite Montserrat, a British Overseas Territory, is a melting pot of Caribbean and European cultures and traditions. The island’s active volcano Soufrière Hills, which last erupted in the 1990s, gives the island its signature black sand beaches—but it also makes the lower two-thirds of the island a generally off-limits “exclusion zone.” The north of the island, however, is home to stunning coral reefs and shoreline caves, perfect for eager explorers.

Stay here: Take in stunning sunsets from the porch of this Old Town cottage, lacquered in shades of blue that echo the seas and skies of the Caribbean. Breezes off the bay keep you cool and relaxed. Be sure to rent a car so you can hop into town or take a day trip to the north of the island. Rates from $64 per night.

Trinidad and Tobago

$123 per night average
Just off the northeast coast of Venezuela sits the dual island nation of Trinidad and Tobago. Known for its raucous Carnival and distinctive Creole cuisine, these Caribbean islands feature white sand beaches, dense mangroves, and lush rainforests. The republic is prized among bird watchers and divers alike, and the smallest island, Tobago, is renowned for its pristine beaches.

Stay here: This two-bedroom cabin sits above Erasmus Cove, on the northeast coast of Tobago. Your views are of tropical gardens, rainforest, and Bloody Bay below. You’ll be tucked away from the bustle of the island, but you’re close to town if you need to shop or grab a bite to eat. You also have access to secluded beaches so you can really feel like you’ve escaped the world. Rates from $140 per night.

Curaçao

$126 per night average
Curaçao is part of the Dutch Antilles, a collection of Caribbean islands just a few dozen miles off the northwest coast of Venezuela. This petite island is prized for its incredible diving and snorkeling sites, but it’s a rising star in the Caribbean culinary world, too. The capital, Willemstad, is vibrant and colorful, with Colonial-era buildings that are vaguely reminiscent of the row homes of Amsterdam.

Stay here: If you want to stay in the vibrant capital, this Willemstad apartment will call to you. Rates start at $85 per night. But if it’s quiet (and ocean views) you seek in your Caribbean getaway, head for this Jan Kok villa (pictured), with its wrap-around portico for laidback sunset watching. Take advantage of the neighborhood’s amenities, including restaurants, bars, a wellness center, and pool. Walk to the nearby beach for a quick snorkel or swim, or hop into a car and explore the island’s dozens of snorkel and dive sites. Rates start at $115 per night.

Puerto Rico

$160 per night average
Puerto Rico is bouncing back as it rebuilds from Hurricane Maria’s devastation in the fall of 2017. The Caribbean island and unincorporated U.S. territory is priced right to draw tourists back to the country with flights as low as $115 dollars from some East Coast airports. Spend a day in Old San Juan and explore the island’s Spanish colonial buildings and fortresses. When you’re ready to relax, grab a spot on one of the pristine beaches or snorkel with sea turtles.

Stay here: Casita Fresca in Rincon is an island dream, with two bedrooms, an outdoor shower, and lush tropical surroundings that provide privacy. The west coast home, which is powered by solar energy, is a brief one-mile walk to the beach, or you can take a quick drive to many of the island’s other beautiful golden shores. You’re not far from downtown Rincon either, with its shops, restaurants, and beaches that are ideal for surfing. Rates start at $110 per night.

St. Lucia

$193 per night average
For eager hikers, the eastern Caribbean island of St. Lucia provides exquisite views from the Pitons, a pair of volcanic spiked mountains, which are also a World Heritage Site. If your vacation goals revolve around cucumber spa water, oversized sunglasses, and big hats, you’ll still find a lot to love, with St. Lucia’s luxurious beaches, waterfalls, and unparalleled vistas.

Stay here: In this Balinese-inspired cottage, you can perch yourself atop the tropical canopy and gaze at Rodney Bay and Pigeon Island for a vista like nowhere else on St. Lucia. The cottage is just a short walk from beaches, and a five-minute car ride to the village of Gros Islet. Rates start at $99 per night.

Bonaire

$199 per night average
This boomerang-shaped Dutch Antilles island is quiet and humble compared to its sister islands, Aruba and Curacao, but don’t sleep on Bonaire. Divers and snorkel enthusiasts around the world know the beauty that lies just offshore this Caribbean island. The immense Washington Slagbaai National Park is home to wild donkeys and birds, and you’ll be sure to catch a glimpse of iguanas just about anywhere you go.

Stay here: Stay in the main town Kralendijk if you want to be close to restaurants and bars. If you don’t mind driving, set up outside the main drag for great prices and beautiful beachfront homes like this two-bedroom villa. This rental is beside Beyond the Corals, an excellent dive resort, and you’ll have access to their facilities if you stay here. The villa is surrounded by lush gardens and features a private pool so you can go for a dip after your day of diving, lounging, or snorkeling. Rates start at $129 per night.

Jamaica

$212 per night average
Jamaica is renowned for its private all-inclusive resorts and lush, secret bays. All too often, however, those come with a hefty price tag. Jamaican bargains can be found if you know where to look. Seek out accommodations around Port Antonio, Ocho Rios, and Treasure Beach. These locations are laid-back but offer unique vibes that make this island so special.

Stay here: This Treasure Beach house captures the essence of Caribbean living, with its broad beach views, understated-but-elegant decor, and coastal breezes to keep you cool all day and night. A cook/housekeeper and live-in caretaker are also happy to show you around the grounds and introduce you to the many fruit trees and palms. Rates start at $150 per night.

Saint Vincent and the Grenadines

$273 per night average
This southern Caribbean island nation consists of a series of 32 smaller islands and cays, many of which are entirely off-the-grid of traditional Caribbean travel. Saint Vincent and the Grenadines provide safe harbor to many yachts and sailboats and acts as the home base to multiple private islands in this part of the sea. But away from the boats, the nation is also home to idyllic beaches and rugged, mountainous landscape.

Stay here: Union Island sits at the far southern end of the archipelago, and it’s the ideal location for adventurous travelers who don’t mind taking an uncharted path. The island is home to no major resorts but several low-key towns, which makes mixing and mingling with the locals natural. Make this Union Island house your home base for your stay in the Grenadines. You’ll be able to see nearby Mayreau Island and Tobago Cays, which you can hop to for the day via a ferry.

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