Caribbean vacation rentals
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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
Home in Santa Marta
4.98 out of 5 average rating, 117 reviewsCasa Palenque - Amazing retreat with private pool
Cottage in Jiménez
4.93 out of 5 average rating, 310 reviewsThe Bear's House - Jungle Cottage with river
Home in Central Eleuthera
4.94 out of 5 average rating, 101 reviewsHeart & Soul, Ocean View, Private Pool & Gardens
Rental unit in Bouillante
5 out of 5 average rating, 33 reviewsVaneïa - Exceptional Duplex, Panoramic Sea View
Home in Río Grande
4.91 out of 5 average rating, 138 reviewsPrivate Beachfront Home - Weather Guarantee*
Rental unit in Grand Cayman
4.98 out of 5 average rating, 115 reviewsAdorable Boho Beach Villa
Cottage in Guardalavaca
4.91 out of 5 average rating, 129 reviewsCabañita La Roca Beach Front Cottage,Guardalavaca!
Villa in Saint Barthélemy
4.97 out of 5 average rating, 139 reviewsVilla RIDE
Caribbean beachfront vacation rentals
Cottage in Rainbow Bay
4.95 out of 5 average rating, 140 reviews**NEW LUXE Villa Soreli - 1 B/R Oceanfront w/Pool
Place to stay in Quebradillas
4.85 out of 5 average rating, 112 reviewsShalom on the Cliff (White) Luxury Suite
Home in Borinquen
4.96 out of 5 average rating, 270 reviewsThe Nest at Crash Boat. Only waterfront on Beach
Villa in Punta Rucia
4.94 out of 5 average rating, 173 reviewsVilla Mango "Exclusive BeachFront"
Villa in St. Thomas
4.89 out of 5 average rating, 104 reviewsNew Waterfront Villa on Magens bay, with Jeep
Hut in Bavaro
4.91 out of 5 average rating, 505 reviewsHut #1 Romantic Luxury Beachfront
Home in Governor's Harbour
4.97 out of 5 average rating, 108 reviewsCayo Loco Villa On Deserted PinkSand Beach for 2!
Cottage in Les Anses-d'Arlet
4.94 out of 5 average rating, 109 reviewsMini Villa T1 private pool sea view and sea access.
House rentals in Caribbean
Home in Providenciales
4.97 out of 5 average rating, 317 reviewsVilla Cocuyo Micro Villa with pool
Home in Providenciales
5 out of 5 average rating, 33 reviewsPrivate beach, Pool & Master Suite
Home in Las Terrenas
4.97 out of 5 average rating, 110 reviewsLa Dépendance de Villa Maguà
Home in Gregory Town
4.97 out of 5 average rating, 38 reviewsUnique designed ocean view home
Home in Hacienda Pinilla, Santa Cruz
5 out of 5 average rating, 157 reviewsPlumeria Guest House
Home in Cabarete
4.99 out of 5 average rating, 135 reviews"La Casita"- cozy 1 bedroom apartment with patio
Home in Saint-Barthélemy
4.96 out of 5 average rating, 139 reviewsNorth Star
Home in Cartagena
4.96 out of 5 average rating, 184 reviewsCartagena walled casa Mónaco
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.
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