Vacation rentals in Caribbean
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Top-rated vacation rentals in Caribbean
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Vacation rentals for every style
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Popular amenities for Caribbean vacation rentals
Private vacation rentals in Caribbean
"Tumbleweed Cottage"
Beautiful View Chalet
RARE Sept SALE! OPEN! Sarasota #1 Lux BEACH Villa
Secret Dome 2 with a lake view
Ocean front luxury villa in Malmok Aruba
Deluxe Tree house! Jacuzzi and ocean view!
Sunset Hill, Rincón | Romantic Chalet & Tree House
O'reilly Loft
Home rentals in Caribbean
Ocean Hill Villa Coral Estate Curacao
Ocean view with private pool house: Isabela #6
Ocean View, Private Pool, & Large Botanical Garden
Suite with Private Pool
Airstream With Pool, Amazing Ocean & Nature Views
Waterfall House
Villa Jeremi
Cayo Loco Villa 2 Deserted PinkSand Beach 2 Adults
Bungalow rentals in Caribbean
Blue Palm Residence - "Le Pavillon" - St François
Bougie Bungalow at the Beach
The Village
Playa Bonita Beach Houses - truly on the beach!
Sailor's Rest, a Romantic and Luxurious Sanctuary
Eden Eco Bungalow, La Fortuna
Bungalow SO CUTE, romantique, piscine privative!
Mother Nature
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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