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Vacation rentals in Caribbean
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Caribbean
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Popular amenities for Caribbean vacation rentals
Private vacation rentals in Caribbean
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Cottage in Monteverde
4.95 out of 5 average rating, 141 reviewsMiramar Cottage - Nestled in the Cloud Forest!
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Villa in Indigo Bay
4.95 out of 5 average rating, 106 reviewsVilla Life is Good
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Guesthouse in Cabo Rojo
4.86 out of 5 average rating, 548 reviewsThe Cabin in the Forest
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Treehouse in Matapalo
4.97 out of 5 average rating, 175 reviewsBohemian Chic Tree House with magical views
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Villa in Camuy
4.95 out of 5 average rating, 277 reviewsVilla Renata ⛵️Beachfront house🏝 private Pool 🏝
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Cottage in Montego Bay
4.94 out of 5 average rating, 180 reviewsGlory @ Montego Bay
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Hut in Villalba
4.89 out of 5 average rating, 872 reviewsTherapy, a dream cabin
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Guest suite in Ocho Rios
4.92 out of 5 average rating, 118 reviewsLuxury White Sand Beach Cottage 1 bd with Chef
House rentals in Caribbean
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Home in Borinquen
4.96 out of 5 average rating, 247 reviewsThe Nest at Crash Boat. Only waterfront on Beach
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Home in Willemstad
4.95 out of 5 average rating, 146 reviewsPrivate Oceanfront luxurious city villa with pool
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Home in Nassau
4.94 out of 5 average rating, 150 reviewsSunrise by the Sea - the ocean on your doorstep!
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Home in Punta Rucia
4.99 out of 5 average rating, 151 reviewsVilla Arena - Beach Front
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Home in Tortola
4.93 out of 5 average rating, 125 reviewsPrivate One Bedroom Villa, HotTub, Amazing Views
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Home in San Cayetano de Venecia
4.96 out of 5 average rating, 146 reviewsQuinta La Ceiba Modern Home with Pool in DairyFarm
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Home in San Carlos Alajuela
4.92 out of 5 average rating, 179 reviewsArenal Kabata luxury infinity and jacuzzi spa
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Home in Jarabacoa
4.97 out of 5 average rating, 224 reviewsVilla Romantica for couples , jarabacielo
Private houses in Caribbean
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Home in Providenciales
4.96 out of 5 average rating, 304 reviewsVilla Cocuyo Micro Villa with pool
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Home in Providenciales
4.95 out of 5 average rating, 156 reviewsModern Caribbean 1 - Breathtaking Views & Pool
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Home in Rincon
4.93 out of 5 average rating, 325 reviewsCasa Mariola
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Home in Nassau
4.82 out of 5 average rating, 168 reviewsCima del Mar Instagram: @cima_del_mar
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Home in st thomas us virgin islands
4.9 out of 5 average rating, 259 reviews" ladyDove " on lovely magens bay
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Home in Grace Bay
4.97 out of 5 average rating, 127 reviewsFollow Your Dreams Villa!
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Home in Calabash Rd, Cole Bay
4.93 out of 5 average rating, 119 reviewsTHE HILL HOUSE, 2 Bdr, pool, panoramic view
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Home in George Town
4.88 out of 5 average rating, 77 reviewsThe Best Views are the ones we share with you.
Your guide to Caribbean
All About the Caribbean
The Caribbean is made up of 26 island countries surrounded by bejeweled blue and green waters and is known around the world as a holiday paradise. People flock here, especially in the winter, for warm sands, golden sunshine, and that sense of island time abandon — plus, the fruity drinks under towering palm trees. The Dominican Republic is the most visited of all the islands due to its vibrant city and cultural life and postcard-perfect beaches. West of that is Cuba, famous for its Old World architecture, rich jazz and music scenes, and several UNESCO World Heritage Sites. Closer to South America is little St. Lucia, known for its rainforests, colorful coral reefs (perfect for diving and snorkeling), and, of course, pristine beaches surrounded by the island’s volcanic peaks.
The countries in the Caribbean are extremely diverse, not only in their histories, cultures, and languages, but their landscapes and topographies. For example, vibrant Jamaica could not be more different from super-chill Aruba and swanky St. Barts. So whether you’re seeking an island that’s large or small, glitzy or low-key, in the Caribbean there is a sanctuary for everyone.
The best time to stay in a vacation rental in Caribbean
Thanks to trade winds, the weather in the Caribbean is sunny and pleasant all year round. The only caveat is that tropical storms and hurricanes occur to varying degrees of intensity here, and their likelihood increases from about July to November. But it’s the dry season from December through March that makes the region so popular. Villas to rent in the Caribbean are in demand during the winter, as many feel the urge to escape the colder weather up north and take in the sun, fun, and the many festivals — like Trinidad’s Carnival, the biggest of the Caribbean’s carnivals, and the Bahamas’ Junkanoo, a cultural street festival and celebration dating back centuries that takes place between Boxing and New Year’s Day. There are also plenty of Caribbean rentals in May and June, if you don’t mind the chance of a little rain.
Top things to do in Caribbean
Santo Domingo
Santo Domingo, the capital of the Dominican Republic, is the oldest continuously inhabited colonial settlement in the Western Hemisphere and was founded in 1496. The historic city center, Zona Colonial, is a UNESCO World Heritage Site, with cobblestone streets, colorful houses, and colonial-style architecture and structures like the 16th-century Basilica Cathedral of Santa María la Menor, the oldest surviving cathedral in the Americas.
Curaçao
Sitting off the coast of Venezuela is the Dutch island of Curaçao, lesser known than its neighbors, but with just as much to offer — including its lack of hurricane seasons. Willemstad, the capital, is one of the few UNESCO World Heritage cities in the Caribbean, and it’s pulsing with nightlife and festivals like Carnival and King’s Day. The diving here is top-notch, there are dozens of stunning beaches to choose from, and the lodging ranges from hostels to five-star resorts — so there’s something here for everyone.
Reggae in Jamaica
Jamaica is the birthplace of reggae. The music took off in the late 1960s, and by the 1970s, with the superstardom of Bob Marley and the Wailers, it became known throughout the world. If you’re in Kingston, check out the clubs, still playing the dub style that made the genre so popular. The best of the best musicians have been known to play at the annual reggae festival held in June.
Destinations to explore
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