Vacation rentals in Caribbean
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Top-rated vacation rentals in Caribbean
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Other great vacation rentals in Caribbean
Guest suite in Ocho Rios, Jamaica
4.91 out of 5 average rating, 114 reviewsLuxury White Sand Beach Cottage 1 bd with Chef
Mar 25 – Apr 1
Villa in Sosúa, Dominican Republic
4.86 out of 5 average rating, 113 reviews836 CASALINDA
Mar 6 – 13
Home in Borinquen, Puerto Rico
4.96 out of 5 average rating, 235 reviewsThe Nest at Crash Boat. Only waterfront on Beach
Sep 30 – Oct 7
Home in Nassau, Bahamas
4.94 out of 5 average rating, 146 reviewsSunrise by the Sea - the ocean on your doorstep!
Sep 13 – 20
Villa in Santa Teresa beach, Costa Rica
4.96 out of 5 average rating, 106 reviewsVilla Melody
May 11 – 18
Apartment in Fitts Village, Barbados
4.94 out of 5 average rating, 108 reviewsLa Porta Della Casa - Sunset Platinum West Coast
Oct 20 – 27
Houseboat in Key West, Florida
4.84 out of 5 average rating, 177 reviewsHappys Houseboat
Nov 30 – Dec 7
Villa in Soufriere, St. Lucia
4.86 out of 5 average rating, 166 reviewsVilla Piton Caribbean Castle
Jan 18 – 25
House rentals in Caribbean
Home in DO, Dominican Republic
4.92 out of 5 average rating, 303 reviewsBeautifull Guest House with panoramic views
Dec 5 – 12
Home in Cartagena, Colombia
4.95 out of 5 average rating, 171 reviewsCartagena walled casa Mónaco
Apr 12 – 19
Home in Naples, Florida
4.98 out of 5 average rating, 208 reviewsIsland lifestyle family vacation home (Salt Pool)
Mar 24 – 31
Home in Punta Rucia, Dominican Republic
4.99 out of 5 average rating, 142 reviewsVilla Arena - Beach Front
Feb 7 – 14
Home in Rincon, Puerto Rico
4.91 out of 5 average rating, 205 reviewsCasa Ensenada- Rincon Puerto Rico
Nov 11 – 18
Home in Lake Worth, Florida
4.97 out of 5 average rating, 157 reviewsTropical Beach Villa with Heated Salt Water Pool
Dec 14 – 21
Home in Adjuntas, Puerto Rico
4.97 out of 5 average rating, 183 reviewsSecluded Coffee Farm House w/Chimney & Heated Pool
Apr 5 – 12
Home in Stake Bay, Cayman Islands
5.0 out of 5 average rating, 36 reviewsModern Oceanfront, 2Primary Suites, sleeps 6, pool
Apr 20 – 27
Cottage rentals in Caribbean
Cottage in Monteverde, Costa Rica
4.94 out of 5 average rating, 127 reviewsMiramar Cottage - Nestled in the Cloud Forest!
Sep 17 – 24
Cottage in Rincón, Puerto Rico
4.93 out of 5 average rating, 343 reviewsCozy, private oceanfront beach house in Rincón
Oct 5 – 12
Cottage in La Romana, Dominican Republic
5.0 out of 5 average rating, 141 reviewsChic Cottage Nature Casa de Campo
Jun 4 – 11
Cottage in Monteverde, Costa Rica
4.97 out of 5 average rating, 158 reviewsVilla 3 - Heated private pool and amazing sunsets
Aug 31 – Sep 7
Cottage in Punta Uva, Costa Rica
4.92 out of 5 average rating, 202 reviewsThe White Cottage, Punta Uva Beach, Costa Rica
Jul 1 – 8
Cottage in Central, U.S. Virgin Islands
4.99 out of 5 average rating, 133 reviewsCaribbean Style Cottage
Mar 8 – 15
Cottage in San Isidro, Costa Rica
4.92 out of 5 average rating, 130 reviewsCountry house with panoramic view
Jun 8 – 15
Cottage in Ocho Rios, Jamaica
5.0 out of 5 average rating, 414 reviews"Tumbleweed Cottage"
Nov 28 – Dec 5
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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