There’s no single version of the Caribbean. Sure, the water is blue—sometimes turquoise, sometimes electric teal—but the similarities start to splinter from there. Some islands are lush and volcanic, with rainforests spilling into the sea; others are dry and desertlike, dotted with cactus and wind-bent divi-divi trees. In St. Barts, you might hear French and smell fresh-baked baguettes. In Dominica, you’re more likely to follow the sound of a waterfall than the beat of a beach club.
Though the region’s resorts and hotels are incredible, travelers who want to tap into the kaleidoscopic variety of the Caribbean should consider a stay in a locally-owned Airbnb. From an overwater bungalow in the Bahamas to an art-forward hideaway steps from jungle treks in Trinidad, these are some of the most memorable places to stay in the Caribbean right now.
Perks: Outdoor dining area, complimentary shuttle, garden shower
Tucked a short stroll from Grand Cayman’s iconic Seven Mile Beach, this one-bedroom cottage offers a polished take on island living. The cottage leans into a minimalist coastal aesthetic—think soft neutrals, natural textures, clean lines, and wood paneling. The living area is compact but airy, with a sleeper sofa and a desk if you must check your emails between swims, while the kitchen offers enough gadgets to make everything from gourmet coffees to full meals. In the bedroom, a king-size bed outfitted in crisp white linens sits against a paneled feature wall. However, it’s the pool that steals the show—framed by leafy palms and tropical flowers and paired with loungers shaded by fringed umbrellas, it’s the perfect spot for slow mornings or cocktail-fueled sunsets. The vibe is quiet and residential, yet you’re just minutes from the restaurants, snorkeling spots, and powder-soft sands. From $400 per night.
Perks: Jacuzzi, large terrace, mountain-top views
Waking up here feels like floating above the forest. Tucked into the hills above Jarabacoa—one of the Dominican Republic’s most scenic mountain towns—this modern guesthouse is wrapped in floor-to-ceiling windows that frame sweeping views of the valley below. From the bed, you can watch the sunrise spill over the peaks without even reaching for your slippers. Just beyond the glass: rolling green hills, drifting clouds, and a soundtrack of birdsong. The design is smart and simple, with a natural palette that echoes the surrounding landscape. There’s a full kitchen for cooking (or reheating empanadas purchased in town), a spacious terrace that makes the most of the view, and a private jacuzzi out front might be the best seat in the house. From $308 per night.
Perks: Soaking tub, terrace, full kitchen
Tucked between misty green mountains and the glassy expanse of Lake Dos Bocas, Villa Limón feels like something out of a dream. Perched on the second floor of a modern duplex at Finca Regina, this one-bedroom suite is all about quiet immersion in nature, with floor-to-ceiling windows framing the lake at nearly every turn. The kitchen is small but thoughtful—stovetop, mini fridge, and locally minded staples like olive oil, milk, and good coffee already waiting for you. The bathroom is generous in size and spa-like in vibe, with an oversized shower and clean, modern finishes. And in the master bedroom, a queen-sized bed and a freestanding soaking tub offer opportunities to unwind. Down at the shared sundeck—right on the lake’s edge—you can fish, sunbathe, or melt into a deck chair with a boozy painkiller in hand. Nearby, you’ve got waterfalls, hiking trails, eco-tours, and even a boat taxi to nearby restaurants. From $388 per night.
Perks: Projector, private patio, fully equipped kitchen
Set at the foot of El Tucuche—one of Trinidad’s most storied peaks—this open-plan studio is part cozy mountain basecamp, part creative sanctuary. Designed with eco-tourists and birdwatchers in mind, the space is bright and welcoming, with tall ceilings, pops of color, and an easygoing charm that makes you feel like you’ve landed in a friend’s well-loved artist loft. The layout is wide open, with a raised sleeping platform overlooking the airy kitchen and lounge. Come nightfall, cue up Netflix on the full-wall projector or pour a glass of rum on the patio overlooking the jungle. From $78 per night.
Perks: Pool with sun loungers, alfresco dining area, large courtyard
If your idea of a perfect Caribbean stay involves waking up to the sound of palm trees rustling, cannonballing into your own private pool before coffee, and then walking to the beach with a cooler full of cerveza, Villa Blanca is likely your kind of place. With four bedrooms to choose from, all of which come with big en suites, it’s a great option for a family trip or a friend group getaway. There is an outdoor bar, BBQ, and full indoor kitchen with everything you need to play private chef (though the 10% discount at nearby One Eleven Beach Club is a pretty tempting alternative). Bonus points for thoughtful beach-day extras: backpack chairs, towels, a cooler bag, and an easy 7-minute walk to the sea. From $979 per night.
Perks: Ocean access, loungers, kitchenette
Perched directly above the gin-clear shallows of the Bahamian sea, this one-bedroom overwater bungalow delivers on that castaway fantasy—just with better linens and Wi-Fi. Inside, the space is bright, airy, and casually stylish. The open layout flows from a king-size bed dressed in crisp white linens to a compact kitchenette stocked for morning coffee and easy island meals. And oh, the view. Whether you’re sunbathing on the deck, taking a morning plunge, or cueing up a movie on the projector after dark, the sea is your constant backdrop. Better yet, add-ons like private chef dinners, boat tours, massages, and grocery delivery mean you can go full vacation mode from the jump. From $434 per night.
Perks: Continental breakfast, infinity pool, sweeping views
If you’re looking for a place to celebrate a milestone birthday, intimate wedding, or family reunion, this six-bedroom villa suspended 500 feet above the Caribbean, with uninterrupted sightlines to the Pitons (a pair of volcanic spires), is pretty special. Each of the rooms is open to the elements but still deeply comfortable, with mosquito-netted four-poster beds, teak louvered doors, and ensuite bathrooms. (The only window on the property is a single porthole in the master suite that peers into the pool.) There’s also a breezy living and dining space, a self-serve guest bar, a 48-foot infinity pool flanked by lounge decks, plunge pools, and an outdoor kitchen ready for making cocktails and grilled snapper. From $1,615 per night.
