The 40 Dreamiest Island Airbnbs in the Caribbean

The Caribbean, a far-reaching archipelago of over 7,000 islands, islets, reefs, and cays, offers a tapestry of experiences, from luxury tourist hubs to secluded, untouched paradises. It can feel overwhelming trying to navigate which island is right for you. So why not start with selecting your dream vacation home? From the luxurious villas of Anguilla to the eco-friendly retreats of Dominica, I’ve chosen the best Airbnbs across Antigua and Barbuda, Aruba, the Bahamas, Barbados, the British Virgin Islands, the Cayman Islands, Curaçao, Grenada, Jamaica, Turks and Caicos, and many more. Whether you seek the culture of Jamaica, the powder white beaches of St. Barts, or the world-class shore diving of Bonaire, these outstanding Airbnbs will allow you to have a more authentic experience of Caribbean life, ensuring an unforgettable island escape.

We hope you love the Airbnb Caribbean rentals we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.

The small island of Anguilla is situated north of St. Maarten. If you want to skip mega-resorts and endless rows of sun loungers, you’ll find on bigger-name Caribbean islands, this hideaway is where to go to skip the crowds. The island’s peak, from December to April, coincides with higher costs and increased, though still relatively modest, visitor numbers. For a less crowded experience, consider visiting from late April to July. Reaching Anguilla requires a multi-leg journey. Direct flights are sadly not available from the US, so you’ll need to connect through Antigua or St. Maarten. Beyond the beaches, the island is known for its five-star hospitality, which is big on luxury, and its innovative food scene.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

If your budget allows or you have a group of friends with money to burn, this luxury eight-bedroom villa has one of the best locations on the island. Located on the tip of West End, the property sleeps over 16 guests in eight suites, offers an array of indoor and outdoor living spaces with views over the Caribbean Sea, and sits above a beautiful sandy cove with exceptional snorkeling. If this is out of your price range, this four-bedroom villa ($1,870 per night) sleeps a smaller group of eight but has an infinity pool and is a stroll from an award-winning beach, Rendezvous Bay. For couples wanting a luxe stay, check out this new beachfront penthouse ($695 per night) directly on the beautiful Sandy Ground Beach.

16+ guests, eight bedroom
Price: $6,000 per night

Antigua might not have a dramatic landscape like some neighboring islands, but it is famous for having 365 beaches, out of this world sailing conditions, and friendly locals. The island tourist traffic peaks from mid-December until Easter. Antigua Sailing Week, held near English Harbour in late April, is a major event for those interested in sailing and other cultural festivities, such as the island’s Carnival in late July, which is worth planning a trip around.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

For an Airbnb with a view of the regattas this four-bedroom villa will do nicely. It has a stunning infinity pool overlooking the turquoise sea, oodles of deck space and direct access to a dock and the ocean. It’s within a private gated community, has a lovely tropical garden and secure covered parking for two cars (which is excellent for those who want to rent a vehicle to explore the island). Another option within a gated development is this high-end luxury beach house ($1,500 per night). It’s situated in a secluded (and exclusive) part of Jolly Harbour and sleeps 13 guests. If those are too grand, this colorful holiday apartment ($200 per night) is only five minutes’ walking distance from Jolly Harbour center, and although it lacks a pool, you’ll be seconds from Jolly Beach.

Eight guests, four bedrooms
Price: $1,275 per night

Aruba sits fifteen miles off Venezuela’s coast. While it holds the title of the smallest of the Dutch ABC islands, it offers an array of activities and thanks to its compact size, it’s easily navigable by car. Aruba’s snorkeling rivals its neighbors, with coral reefs packed with marine life, including turtles and parrotfish. If you dive, or have an interest, you can explore shipwrecks and sunken aircraft just off the coast. Direct flights are available from numerous US major cities, and the absence of a rainy season makes the island a year-round destination.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Located in Savaneta, the oldest town in Aruba and former capital, a stay at this stunning beachfront suite will allow you to experience authentic Aruban life away from crowded tourist areas. The private patio leads directly onto the powdery white sand. There’s a hammock for afternoon naps and an outdoor kitchen and dining area for romantic meals with the soundtrack of lapping waves. If that’s not in your budget, this one bedroom ($74 per night) is another top percent listing in the quiet and safe neighborhood of Noord just 15 minutes from the beach. For groups, you’re also spoilt for choice. At the higher end of the market is this brand-new beachfront four-bedroom villa ($1,313 per night). It’s ticking all the boxes with a 20-meter lap pool, jaw-dropping views and a hot tub.

Two guests, one bedroom
Price: $630 per night

The Bahamas is a group of seven hundred islands, each with powder white beaches, historic colorful towns, and surrounded by some of the most beautiful coral reefs in the world. The timing of your trip to the sprawling archipelago matters. During peak season, when prices surge, there is a flood of visitors. Consider the shoulder seasons for a balance of pleasant weather and fewer crowds. To reach the Bahamas from the US, direct flights are frequent from major East Coast cities to Nassau’s Lynden Pindling International Airport. From there, domestic flights and ferry services connect to other islands.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

When planning a trip to the Bahamas, you might begin with choosing which island, or you could put more importance on finding a vacation rental of your dreams and go from there. For that, you’ve got a lot to choose from. Across the islands, there’s an Airbnb that suits every type of traveler. For someone visiting alone or in a couple, this overwater bungalow in George Town is a top five percent Airbnb. As you’ll be sleeping directly over the water, you can wake up and dive into the crystal-clear waters of Exuma from the deck. Families who need more space, should bookmark this stunning beach house ($600 per night) in Governor’s Harbour, on Central Eleuthera. Sliding glass doors lead out onto one of the best beaches in Eleuthera and this family-friendly two-bedroom offers a casual coastal vibe while still feeling cozy (not to mention a million dollar view).

Two guests, one bedroom
Price: $520 per night

Barbados is one of the most popular islands in the Eastern Caribbean. It largely caters to those looking for the generic Caribbean resort experience. But if you’d like to skip the over-priced daiquiris, Barbados retains a distinct personality, a regional cuisine, some stunning natural areas, world-class surf, and plenty of local traditions and culture. To reach the island from the US, direct flights operate from major hubs like Miami, New York, and Charlotte, landing at Grantley Adams International Airport. The journey, dependent on your departure point, is generally easy, around four to five hours.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

The Airbnb scene in Barbados has everything from sprawling luxury villas and lavish penthouses to affordable apartments near popular surf spots. If interior design matters to you, this boutique house is perfectly located next to the beach by Holetown on the West Coast. The bright and airy three-bedroom has vaulted ceilings and a crisp, white aesthetic. Outdoors there’s a pool, a grill, private gated gardens and an outdoor bar. To add a touch more luxury, the host includes a housekeeper and full concierge service, which can arrange a private chef and driver. Couples should look over this waterfront apartment ($207 per night) on the prestigious west coast of Barbados. The Greek-style property offers breathtaking 180-degree views over one of the island’s most beautiful and tranquil bays. This three-bedroom villa ($535 per night) on Barbados’ Platinum Coast is ideal for small groups and families with a mid-range budget. It’s a top 10 percent Airbnb within a private gated community with a communal swimming pool and a short stroll from Gibbes Beach.

Six guests, three bedrooms
Price: $1,895 per night

Bonaire isn’t your typical Caribbean lushness; think cacti and divi-divi trees bent by constant trade winds. Its reputation as a diving and windsurfing mecca is well-earned. The island’s entire coastline is a protected marine park, offering accessible shore dives and coral ecosystems. The Dutch Caribbean island smack between Aruba and Curaçao is a shore diver’s heaven. The reef is pretty easy to navigate, there are many dive shops, and dive sites are marked by a yellow stone on the beach, so all you need to do is rent a car, find a base, and traverse the island looking for the best places to dive.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

This stunning oceanfront villa will do nicely as a base for your Bonaire vacation. It’s ideal if you have a mixed group of dive enthusiasts and those who just want to chill in the infinity pool. Perched on cliff terrain, the villa offers a 180-degree panoramic view of the ocean and neighboring Klein Bonaire. It has direct access to the sea through a small private coral stone beach. With the ocean right in your backyard, you’ll be snorkeling distance from one of the lesser explored dive spots, “Barkadera”. A less costly option for a small group is this oceanfront two-bedroom lodge ($374 per night) in Kralendijk. It has rave reviews, a private deck, pool, dive locker, rinse tank, an outdoor shower, and is next to a dive shop for gear rental.

Eight guests, four bedrooms
Price: $1,150 per night

The British Virgin Islands are an all-you-can-eat nature buffet of four large islands (Tortola, Anegada, Virgin Gorda, and Jost Van Dyke) and 32 smaller islands and islets. This is a place where seclusion is prized, attracting those seeking respite from the more crowded tourist hubs in the Caribbean. The sea is crystal clear so there’s exceptional visibility for those exploring beneath the surface. For hikers, you can get views over the Caribbean from the verdant routes to the 1,370-foot summit in Gorda Peak National Park on Virgin Gorda island. And the regions’ tropical winds make the water surrounding the islands a paradise for kitesurfers. Flights from the US typically connect through San Juan, Puerto Rico, or other Caribbean hubs, to Tortola’s Terrance B. Lettsome International Airport.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

This is another region where you might want to put finding the perfect vacation rental before choosing a specific island. You can easily hop between islands on frequent ferry services after all. For a luxe villa, this three-bedroom on Tortola is one to bookmark. The east-facing property offers sunrise views from practically any room and the Rogues Bay location makes it easy to get to all the must-see spots on the island. There’s a king-sized hammock in the garden for afternoon siestas and stargazing, a patio with a BBQ, swimming pool, and ample deck space. Also on Tortola is this one-bedroom villa ($250 per night) on Cooten Bay. It has equally impressive views and a hot tub for romantic nights in.

Six guests, three bedrooms
Price: $600 per night

The Cayman Islands exist as a trio: Grand Cayman, Cayman Brac, and Little Cayman. They sit in the western Caribbean Sea, south of Cuba and northwest of Jamaica. Grand Cayman, the largest, is home to most of the population and activity. Cayman Brac is excellent for rock climbing, hiking, and birdwatching (the islands are home to more endemic species of wildlife than the Galapagos), and Little Cayman is a haven for divers. Direct flights are available from major hubs like Miami, Atlanta, and New York. The peak season, when the islands experience drier, cooler weather, runs from mid-December to April.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

It would be smart to base yourself on Grand Cayman and island hop to the others. That way you’ll be close to all major amenities. I’d highly recommend avoiding resorts, yes, you get a flop and drop vacation, but having your own home will give you a more authentic experience. For a couple or small family, this cottage is dreamy. Sleeping up to four, it has a resort-style pool, a garden shower, outdoor dining, a heated spa, and there’s a complimentary Land Rover Defender shuttle service that will take you to nearby beaches. If you need more space, consider this family-friendly three bedroom home ($593 per night) in George Town. The two-story house has a beautiful terrace overlooking a private beach. Or if you have a flexible budget, this modern beachview retreat ($1,000 per night) is in Northside. It comes with added extras like watersports gear and is managed by a professional hospitality company.

Four guests, one bedroom
Price: $434 per night

Curaçao’s history as a Dutch trading outpost remains palpable. You’ll note Dutch architectural styles in towns such as the capital, Willemstad. A UNESCO World Heritage site, Willemstad’s brightly colored Dutch colonial architecture lines the Handelskade waterfront. Dutch is still spoken (along with English and Papiamento, a creole language born from Spanish and Portuguese influences). It’s another Caribbean island recognized for excellent diving and snorkeling, with numerous reefs and wrecks accessible from the shore. The island’s weather remains consistently warm throughout the year. And getting there is a sea breeze. You can directly fly from major hubs like Miami and New York.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Curaçao isn’t huge, it’s only 40 miles long, so wherever you choose to stay, you’ll be within driving (or walking) distance to incredible beaches, friendly towns, and historic Willenstad. This oceanfront five bedroom is ideally located in the middle of the island, only 20 minutes from the airport. It’s situated within a five-star gated community of Coral Estate resort. The villa benefits from resort amenities. Next door you’ll find the pool, dive and wellness center, and various restaurants. The best part? You can jump directly from the villa’s deck into the ocean six meters below and swim back to the beach. Couples looking for something special should look at this one-bedroom city villa ($550 per night) in the Pietermaai District of Willemstad. It’s ideal for those who want privacy, a pool and ocean view, but would like to be closer to the town’s great restaurants and live music.

10 guests, five bedrooms
Price: $600 per night

Often overlooked for other islands, Dominica is one of the best-kept secrets of the Caribbean. It’s commonly referred to as “Nature Island,” and the first people who inhabited the island, the Kalinago people, clearly lived in tandem with nature. And they do so still today. Those who came later to build a life here are held to similar standards of respect for the land and ocean — and every living thing in between. This makes Dominica a very special place. In 2026, the island is slated to open an international airport. This will be a game-changer for visitors and will likely increase connectivity with the US dramatically.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

For something a little more unusual, this shipping container conversion was recently added to Airbnb. It’s tucked away on the shore of Batali Beach, which you’ll have private access to. The renovation is outstanding. There are five bedrooms, many of which are ensuites and the owners have perfected the blend of luxury and eco-conscious living. The hosts will go the extra mile to help plan your vacation. They offer airport transfer, grocery stocking, private chef services, and can help plan excursions on the island. For couples and solo travelers, there are lots of charming cottages peppered across the island. This one-bedroom studio solar-powered cottage ($179 per night) is in Calibishie on the northeast of the island. It’s a top 10 percent Airbnb and the booking comes with a complimentary gin tasting and tour of the on-site gin distillery.

Nine guests, five bedrooms
Price: $1,400 per night

If you’d like to skip the cookie-cutter postcard island, Grenada’s black sand beaches, waterfalls, lush landscape and food scene offer a different Caribbean vacation. The aptly named “Spice Island” is one of the world’s largest nutmeg exporters, with five chocolate factories on the island and three rum distilleries. And it’s not that difficult to get to. Direct flights from New York and Miami will get you there in around five hours.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

This Airbnb is baller. If you have the funds, the two-acre waterfront retreat will make one heck of a base for exploring the island. The five-bedroom estate comes with concierge services, housekeeping, a tennis court, and a stone’s throw from the waterfront of Westerhall Point. For something more realistic, this eco-cabin ($85 per night) is another top listing with glowing reviews from previous guests. The one-bedroom sits high in the trees overlooking Saint George’s harbor. Or if you need more space, this two-bedroom villa ($250 per night) in Crochu has everything you need: a pool, ocean views, and a beach at the bottom of the garden.

10 guests, five bedrooms
Price: $636 per night

Martinique, a slice of France adrift in the Caribbean, sits in the Lesser Antilles, south of Dominica and north of Saint Lucia. For those seeking to escape the North American winter, the dry season, from December to April, offers the most reliable weather. Expect warm, sunny days, perfect for exploring the island’s volcanic landscapes, lush rainforests, soaring peaks and postcard-perfect beaches. Martinique is known for its rhum agricole, a distinct style of rum made from fresh sugarcane juice, not molasses. Distilleries dot the landscape, offering tours and tastings. The island’s cuisine reflects its blend of French and Caribbean influences. Come here hungry for seafood, and don’t skip local specialities such as accras (fritters), and Colombo, a fragrant curry stew.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

First things first. You’ll need a car on Martinique to explore hidden beaches and hop in and out of town. This villa is located on the waterfront, a three-minute drive (or a 20 minute stroll) from Diamond Beach on the southeast coast. The views from the four-bedroom look out over the south of Martinique and over to Diamond Rock. The host offers a concierge service to help with excursions and support those traveling with young family members. Another top listing in the south is this one bedroom villa ($436 per night) in Le Diamant. If you’re looking for somewhere special for an anniversary or honeymoon, this ticks all the boxes. It also has jaw-dropping views of Diamond Rock, a swimming pool with a submerged beach and direct access to the ocean.

Nine guests, four bedrooms
Price: $824 per night

If there’s one Caribbean island that needs no introduction, it’s Jamaica. It’s one of the most popular destinations in the region. Summertime is ideal for hitting the island, yes you’ll have company, but there’s no real escape for that. Getting there is a relatively straightforward affair, with numerous direct options available from major US cities.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Airbnb rentals in Jamaica offer more than just a place to stay; they provide an opportunity to immerse yourself in the culture and beauty of the island. This cottage in Runaway Bay is located directly on a beautiful beach which is perfect for a morning swim. The colorful home has a beachside patio with hammocks and outdoor furniture where you can relax in the afternoon with a book. It has an open-planned layout with one bed in the main living area and one in a loft space above. Nearby you can take glass-bottom boat rides, go beach horseback riding, and scuba dive. If you have a larger group, check out this epic villa ($500 per night) in Treasure Beach. It’s fully staffed and situated on one of the highest points in the area. From here you’ll have panoramic views of the Caribbean Sea and magnificent sunsets from the large, shaded verandah, sun deck, and pool that spans the length of the home.

Four guests, one bedroom
Price: $300 per night

St. Kitts and Nevis, a twin-island nation barely a blip on most maps, sits where the Atlantic meets the Caribbean. St. Kitts, the larger of the two, is packed with outdoor adventure activities, while it’s more tranquil sister island is where to go to simply do nothing (other than enjoy the the laid-back Caribbean vibes). While the islands’ small size might suggest remote access, they are surprisingly well-connected. There are direct flights from major East Coast hubs like Miami, New York, and Charlotte, but it’s likely you’ll need to stop off at neighboring Caribbean islands like Puerto Rico.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

This four-bedroom villa is conveniently located within the gated beachfront community of Sandy Bank Bay, within Christophe Harbour on St. Kitts’ famed Southeast Peninsula. Perfect for entertaining (or keeping an eye on kids) as the front sliding doors open to the private pool and deck area with sun loungers and a covered seating area. All bedrooms have an ensuite and there’s central air conditioning throughout. Another luxe group option is this wild three story mansion on Nevis ($1,524 per night). The top 10 percent listing offers unobstructed panoramic views of Mount Nevis from every floor, a huge oceanfronted pool, a hot tub, and beautifully manicured tropical gardens.

10 guests, four bedrooms
Price: $830 per night

When you think of St. Barts, you likely imagine beautiful rich people vacationing in opulence, and you’d not be that far off. But there’s more to the island than beach clubs and Rosé-all-day. It’s European ambiance saves a jet-lagged trip to France and stunning natural wonders are plentiful. If nothing more, casually saying you vacationed in St. Barts is brag-worthy.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Airbnbs here can be lavish and expensive, but you get a better deal than an island hotel or resort stay. For views, this brand new villa is perfectly positioned overlooking the magnificent bay of Grand Cul de Sac. The interior is tropical and modern, and there’s a seamless flow to the indoors / outdoors layout. For something more reasonable, this one-bedroom guesthouse ($199 per night) has excellent reviews. It has a small kitchen and terrace overlooking the pool, a top-deck to enjoy the sunrise, and a large bedroom overlooking the covered patio with seating area and sea views over Little Anse.

Two guests, one bedroom
Price: $1,326 per night

St. Lucia forms part of the Windward Islands chain. Its topography is defined by dramatic peaks, most notably the Pitons, twin volcanic spires that rise sharply from the sea. The island’s interior is a tapestry of rainforest, fertile valleys, and cascading waterfalls, starkly contrasting neighboring sandy Caribbean isles. There are direct flights from Miami, New York, and Atlanta. To make the most of this beautiful island, you’ll need to rent a car to explore the diverse landscape.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

For a stay to remember, check out this eco-villa. It’s positioned high on a hillside overlooking the Pitons and the Caribbean Sea. The views are simply spectacular. It has an open-air design, and there’s a sprawling infinity pool (plus two other plunge pools) and a deck where you can cool off in the afternoon heat. The host can organise additional services such as private dining, spa treatments and a private driver. There’s excellent snorkeling nearby and Soufriere, the old French capital, is only half a mile away where you’ll find a local market and fantastic restaurants. Another option with an indoor/outdoor feel is this one bedroom treehouse ($159 per night) in Gros Islet on the island’s tip. The canopy hideaway has views over neighboring islands which can be enjoyed from the furnished deck.

14 guests, six bedrooms
Price: $1,750 per night

The 40 low-lying islands and cays that make up Turks and Caicos are where you want to go if you want glamor (without the scene of St. Barts), beaches with sand as pure as white snow, and privacy. Last month, American Airlines launched a direct flight to link Miami with South Caicos, one of the more under-the-radar inhabited islands. The main island of Providenciales (Provo) claims the majority of footfall and just over the turquoise waters are smaller islands that feel more secluded.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

There’s a reason why people gravitate towards Provo. The infrastructure here is well established. You’ll find a slew of water sport operators, restaurants, and bars. On the smaller islands, doing nothing is the main pastime. For solo travelers and couples, this villa on Provo’s Sorrento Beach is perfect for an intimate island retreat. There’s a pool, grill, outdoor seating, and you’ll be steps away from the white sand. The rental also comes with access to nearby tennis courts. For a group vacation home you’ll want to bookmark this top five percent Airbnb villa ($2,970 per night) on the famed Grace Bay Beach on the northeast coast of Provo. It has an open floor layout that merges the indoors with the outdoors. It’s the perfect venue to enjoy an indulgent vacation with friends and family.

Two guests, one bedroom
Price: $1,357 per night