Places to Stay

26 Breezy Caribbean Airbnbs to Escape to This Winter

Soak up those sunny island vibes in Jamaica, St. Barts, Aruba, and beyond.

December 7, 2023

There are 13 countries, 17 dependent territories, and more than 7,000 islands in the Caribbean. Choosing where to spend your travel dollars can be daunting to say the least—so why not let the accommodations lead? The best Airbnbs in the region go head to head with the finest resorts, offering private pools, designer furnishings, phenomenal views, and friendly staff to cater to your every whim. There are sprawling villas for large families and friend groups, romantic bungalows for couples, and cheap but cheerful rentals for budget travelers. Many are mere steps from a pristine beach; others are tucked deep into the jungle greenery. Scroll down to see which island escape best suits your vacation style, starting off with a few Guest Favorites from Airbnb.

We've vetted these listings based on Superhost status, ratings, amenities, location, previous guest reviews, and decor. This gallery has been updated with new information since its original publish date. Additional reporting by Madison Flager.

All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

Providenciales, Turks & Caicos Islands
White sand beaches and turquoise waters are just a few minutes' drive away from this two-bedroom home with gorgeous ocean views. Ideal for a small group trip, the space is bright, airy, and modern, with a full-size kitchen, spacious backyard with a private pool, and a large sunken outdoor seating area that wraps around an electric firepit for cozy nights in (plus a grill, if you feel like barbecuing).
$748 at Airbnb (starting price)

Juana Diaz, Puerto Rico
Past guests refer to this three-bedroom home as a “paradise in paradise” and “by far, the best home we've ever rented.” Tucked away in the mountains of Juana Diaz, you'll enjoy both mountain and ocean views, as well as your own private pool and hot tub. If you must work remotely, there's an office to do so, but we'd rather spend time decompressing on the balcony's egg swings or taking a bath in the primary bedroom's freestanding tub.
$461 at Airbnb (starting price)
Cul de Sac, St.-Martin
Located on the French side of St.-Martin 10 minutes from the Grand Case Airport, this one-bedroom, one-bath home has plenty of space for two to enjoy island living. There's a private pool, copious outdoor living space, a large living room, an open kitchen/dining room, and a bedroom with a double bed. Beaches, restaurants, and a supermarket are all just a five-minute drive away.
$385 at Airbnb (starting price)

West Bay, Cayman Islands
For those looking to veg out on the beach, this Cayman Islands cottage is ideally positioned a minute's drive from the Seven Mile Public Beach. Hosts provide beach chairs, old-school fringed beach umbrellas, and cruiser bikes, which can be checked out at the office; a shared resort-style pool with a heated spa is yours to enjoy, too. The home has room for up to four guests with one king bed and one queen-sized sleeper sofa, and one bathroom. The in-unit washer/dryer is a nice bonus for those who prefer to head home with a suitcase full of clean clothes.
$381 at Airbnb (starting price)
La Vega, Dominican Republic
It's all about the views at this Dominican Republic guest home in the clouds. Guests can gaze out at the mountains from bed, enjoy breakfast on the terrace, and spend time in the outdoor hot tub. It's best suited for couples or solo travelers with one bedroom (it has a double bed) and one bathroom. The kitchenette provides you with the basics: a stove, refrigerator, and kitchen utensils. Guests also gain access to a communal space with a swimming pool, and there is a waterfall a 15-minute walk away.
$261 at Airbnb (starting price)

Courtesy Airbnb
Sawcolts Village, Antigua
With woods and farmland stretching as far as the eye can see, guests at this remote cabin feel like they have the entire island to themselves. A four-wheel-drive vehicle is needed to access the parking area, and Flossie the donkey will help porter your luggage down the narrow path that leads to the rental house. Built on stilts using sustainably harvested local timber and upcycled doors and shutters, the one-bedroom shingled home is completely off the grid—running on rainwater and solar power yet still providing Wi-Fi for those who can’t disconnect. Antique French linens cover the bed, and old louvered barn doors lead to an open-air bathroom ensconced by trees. And though it seems rustic at first blush, it’s loaded with thoughtful amenities: a hammock on the porch, cast-iron pans in the kitchen, and a small writing desk for chipping away at your memoir.
$130 at Airbnb (starting price)

Courtesy Airbnb
Soufrière, St. Lucia
This four-bedroom villa is a 10-minute walk to Anse Chastanet Beach, a fine spot for swimming and snorkeling, but you needn’t leave the hillside property for postcard views of the volcanic spires known as the Pitons. What really sets this property apart, however, are the little things: hand-painted murals, hand-hewn timbers, and walls hung with vintage art and photographs. Guests also sing the praises of the gregarious staff: Gardener Remy, who keeps the pool and grounds tidy; housekeeper Felicia, who cleans and does laundry; and housekeeper Pamela, who makes a mean rum punch to accompany her traditional Creole cooking.
$714 at Airbnb (starting price)
Cruz Bay, St. John, U.S. Virgin Islands
With its cliffside swimming pool, fine Belgian linens, and well-outfitted kitchen (there’s an ice cream maker!), this three-bedroom villa is nothing if not epic. The views of Rendezvous Bay alone are worth the price of admission. Designed by David Moser of storied furniture brand Thos. Moser, the house sports vaulted wood ceilings and custom stonework—plus no shortage of outdoor decks for taking in the dazzling sea view. Even better, the one-acre property sits just 15 minutes from Virgin Islands National Park, a 7,000-acre preserve with immaculate beaches and kaleidoscopic coral reefs.
$923 at Airbnb (starting price)

Courtesy Airbnb
Crochu, St. Andrew, Grenada
Sliding glass doors open onto a large covered terrace and dining room at this contemporary oceanfront villa. The owner’s suite faces white-sand Cabier Beach and Crochu Harbor, while the second bedroom is blessed with rainforest views. The open-plan kitchen is a win for home cooks, while the small dipping pool is perfect for keeping kids entertained. Most importantly, the rental is ideally located for exploring the Levara and Bathway beaches to the north, Grand Anse beach and the capital of St. Georges to the south, and the Grand Etang crater lake at the island’s center.
$245 at Airbnb (starting price)
Courtesy Airbnb
San Juan, Puerto Rico
Art Deco fiends will marvel at the original detailing (those Creole tiles!) in this century-old Santurce mansion. The lovingly restored, three-bedroom rental has three balconies and two spacious sundecks for watching the people of this historic neighborhood go by. The striking midcentury-modern furnishings look as if they were lifted from a magazine spread, while the abundant houseplants will be the envy of any green thumb. The area is rich with restaurants, bars, and shops, and the nearest beach is reachable by foot in 30 minutes.
$208 at Airbnb (starting price)

Courtesy Airbnb
Tortola, British Virgin Islands
This newly remodeled four-bedroom beach villa is owned by restaurateurs, making it a kind of holy grail for home entertainers. The kitchen is outfitted with high-end stainless steel appliances, and there’s a second cooking space—complete with fridge, sink, and barbecue grill—on the upper pool deck. Family and friends can gather around the teak dining table on the covered porch or hang out on the sun loungers and bean bag chairs scattered around the infinity pool. With its surfboard decor and a muted color palette of stone, sand, and soft blues, it’s all very Hamptons-chic. Plus, the outdoor stereo system will keep the party going well into the night.
$719 at Airbnb (starting price)
Courtesy Airbnb
Noord, Aruba
This five-bedroom villa is another Airbnb made for entertaining. Just get a load of that backyard: The swimming pool is decked out with a chic cabana, bean bag loungers, covered yoga pavilion, Food Network–worthy grill setup, and tropical gardens. The interior is just as swoon-inducing, too, with its high vaulted ceilings and bright white kitchen with four-burner twin stoves. Rooms are tastefully appointed with custom furniture, chandeliers, and millwork (much of it imported from Bali), as well as framed photos from the villa owner’s personal travels. The property is especially welcoming of families, providing up to 10 guests (or 14 including children) with air mattresses, a Pack ’n Play, high chair, booster seat, car seat, pool floaties, and beach toys.
$1,019 at Airbnb (starting price)

Courtesy Airbnb
Shoal Bay Village, Anguilla
Indoor-outdoor living spaces are common in Caribbean villas, but not all of them overlook a powdery white sand beach and sparkling turquoise bay. This four-bedroom villa shoulders the mile-long Shoal Bay Beach, but that’s hardly its only selling point. Groups also flock here for its primo chef’s kitchen (complete with a professional gas range stove), formal indoor dining room and casual alfresco seating situation, tiled outdoor hot tub, and private swimming pool. Need a hand in planning your daily excursions? The property manager is happy to assist with car rentals, ferry and taxi reservations, hiring a nanny, or arranging water sports.
$990 at Airbnb (starting price)
Courtesy Airbnb
Vermont, Charlotte, St. Vincent & the Grenadines
From the yin-yang symbol inlaid in the pebbled floor to the orchard brimming with papaya, mango, and soursop, you know you’re in for something special at this Caribbean Airbnb. The yoga studio turned one-bedroom guesthouse is built with stone and enveloped by tropical greenery. Sliding barn doors lead to a bedroom with a carved four-poster bed and Berbice chair, while jalousie windows frame views of the surrounding mountains. From a French press to beach towels, considerate touches abound. And you’re sure to make friends with the local chickens and donkeys when hiking the nearby Vermont Nature Trail.
$95 at Airbnb (starting price)

Courtesy Airbnb
Le François, Martinique
The Hummingbird’s Garden studio earned its name because of the iridescent-winged fowl that dart in and out of the flowers dotting its grounds. Keep an ear out for their sweet hum when dining alfresco on the covered porch, lounging near the modest pool, or chatting up Superhost Marie, who many guests have said was the bright spot of their stay. Not only does she go to great lengths to keep the guesthouse “clean as a surgery room,” past guests rave about her home-cooked meals and helpfulness in planning fun island excursions.
$71 at Airbnb (starting price)
Courtesy Airbnb
Samana, Dominican Republic
Hankering for a jungle getaway but don’t want to give up creature comforts like air-conditioning and 4K TV? Say hello to this one-bedroom, thatched-roof villa with its open-air living room and kitchen, windowed sleeping quarters (translation: fewer bugs!), and seven-foot-by-seven-foot hot tub. The rental is five minutes from the beach—plus you get access to a literal “jungle gym,” a wilderness fitness center where the exercise equipment is made from recycled materials (think barbells with slices of tree trunk for weights).
$158 at Airbnb (Starting Price)

Courtesy Airbnb
Anse Des Cayes, St. Barts
This two-bedroom villa on Anse des Cayes Bay comes with serious bragging rights. Recently featured in Elle Decor France, the elegant property traffics in a neutral color palette, blending modern organic style with beautiful art and sumptuous furnishings. (Check out that gourmet Lacanche range in the kitchen—swoon!) Guests are treated to sweeping ocean views in every room, but many are content whiling away their hours in the hanging bamboo chair or poolside hammock, beach read in hand.
$857 at Airbnb (Starting Price)
Courtesy Airbnb
Spring Farm, Montego Bay, Jamaica
This two-acre Airbnb in Jamaica is located in a gated seaside community close to a golf course and beach. Its five bedrooms accommodate up to 10 guests and the owner’s suite features a king-size bed and en suite bath with a standalone rain shower. There is a dedicated office space for taking Zoom calls and a fan-shaped pool with ocean views for working on that tan. Locally painted artwork is sprinkled throughout the villa, their swirling colors popping against the whitewashed walls. Guests also have access to Rose Hall Beach Club, known for its spotless white sand beach and swaying palms.
$1,113 at Airbnb (Starting Price)

Courtesy Airbnb
Kralendijk, Bonaire
Easy does it at this simple but stylish one-bedroom apartment in Punt Vierkant. The minimalist design is like a breath of fresh air and the price is right for budget travelers—without skimping on amenities. (There’s A/C in the bedroom, a rainfall showerhead in the bath, and a Bluetooth speaker in the living room.) A beach with excellent snorkeling and kite surfing is close by, and guests also rave about Superhost Marjolijn’s delicious stroopwafels and the fun lessons they took at her partner’s kiteboarding school near the house.
$125 at Airbnb (Starting Price)
Courtesy Airbnb
Cupecoy, Sint Maarten
Location, location, location. This two-bedroom oceanfront Eden is just 400 yards from Porto Cupecoy, a mixed-use condo community with a bustling plaza; a 20-minute stroll to breathtaking Mullet Bay; and half an hour to bucket-list favorite Maho Beach (yes, the one adjacent to Princess Juliana International Airport that all the planespotters visit). The kitchen is suitable for making breakfast and doing other light cooking, and there are plenty of restaurants close by. After a long day of roasting on the beach, you’ll thank your lucky stars the apartment has a private dipping pool.
$469 at Airbnb (Starting Price)

Courtesy Airbnb
The Bight, Caicos Islands, Turks and Caicos
Fans of imposing Brutalist architecture would be hard-pressed to find a more formidable villa than this four-bedroom rental near Bight Reef (also known as Coral Gardens), the most popular snorkeling spot in Turks and Caicos. The beach home is a concrete masterpiece, its angular lines softened with midcentury-modern furnishings, carved wooden sculptures, and a halcyon reflecting pool. There are two bedrooms in the main house and two in the guest house—all with king-size beds and ensuite baths with freestanding tubs. Other highlights include a breakfast bar and wine fridge in the kitchen and an L-shaped swimming pool flanked by palm trees. The rate includes daily housekeeping, night security, and laundry service; a private chef, masseuse, and babysitter are available as add-ons.
$2,464 at Airbnb (Starting Price)
Courtesy Airbnb
Anse Des Cayes, St. Barts
This two-bedroom villa on Anse des Cayes Bay comes with serious bragging rights. Recently featured in Elle Decor France, the elegant property traffics in a neutral color palette, blending modern organic style with beautiful art and sumptuous furnishings. (Check out that gourmet Lacanche range in the kitchen—swoon!) Guests are treated to sweeping ocean views in every room, but many are content whiling away their hours in the hanging bamboo chair or poolside hammock, beach read in hand.
$857 at Airbnb (starting price)

Courtesy Airbnb
Holetown, Barbados
The crisp white aesthetic of this three-bedroom villa exudes tranquility. Hidden behind a gated entrance on the Platinum Coast, the house is a 100-meter stroll to the beach and a little over half a mile to Holetown. Soaring ceilings and a spiral staircase make the space feel especially grand; a wine cooler and espresso machine add a whiff of luxury. French doors open onto a private pool and terrace gardens, complete with a plush outdoor sofa, barbecue grill, hammock, and mango tree. The host can organize a chef or driver, while housekeeper Kelly looks after guests’ day-to-day needs.
$750 at Airbnb (starting price)
Courtesy Airbnb
Saint Joseph, Trinidad & Tobago
Calling all eco-travelers: This spacious hillside studio, nestled at the foot of El Tucuche, the second highest mountain peak in Trinidad’s Northern Range, is a siren for hikers, birders, and other nature enthusiasts. When you’re not trekking through lush foliage, enjoy serene views from the gazebo and koi pond or kick back with a Netflix movie projected on the rental’s blank wall. (The host provides 3D glasses and a selection of Blu-rays and DVDs for maximum movie night fun.) Come daytime, pop open the windows to let in buckets of sunshine and the cool tropical breeze.
$71 at Airbnb (Starting Price)

Courtesy Airbnb
North Eleuthera, Bahamas
If your dream vacation involves sipping coffee in a hammock by a “secret” beach, look no further. This two-bedroom cottage sits on a rocky cliff 25 feet above ShoreBreak Beach—an empty slip of sand with sea caves ripe for exploring. (Please use caution—the tides here are no joke.) The cabin was constructed in a traditional Bahamian style by a third-generation local builder and takes its design cues from the gabled wood cottages of Harbour Island. Whitewashed cypress keeps the interior fresh and bright, while porthole windows salvaged from an old passenger liner bring a funky nautical touch. Though it exists completely off the grid (guests must be mindful of their water and solar energy consumption), the house is just a 10-minute walk or five-minute paddle to Surfer’s Beach and two miles to Gregory Town.
$355 at Airbnb (Starting Price)
Courtesy Airbnb
Jan Thiel, Curaçao
It’s hard to put a finger on what exactly makes this five-bedroom villa so alluring: Is it the thatched roof gazebo and twin hammocks edged with tropical foliage? The infinity pool with submersible lounge chairs and knockout sea views? Or the iguanas that freely roam the area, enchanting every kid they meet? The location is walkable to beach clubs and restaurants, but one look at the covered terrace with its enormous 12-person dining table and you may decide to cook every meal at home.
$447 at Airbnb (Starting Price)