Vacation rentals in Caribbean
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Top-rated vacation rentals in Caribbean
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Other great vacation rentals in Caribbean
Cottage in Rincón, Puerto Rico
4.93 out of 5 average rating, 342 reviewsCozy, private oceanfront beach house in Rincón
Apr 13 – 20
Cottage in Monteverde, Costa Rica
4.97 out of 5 average rating, 156 reviewsVilla 3 - Heated private pool and amazing sunsets
Apr 15 – 22
Houseboat in Key West, Florida, US
4.84 out of 5 average rating, 175 reviewsHappys Houseboat
Jan 30 – Feb 6
Bungalow in Monteverde, Costa Rica
4.99 out of 5 average rating, 178 reviewsFika Haus - Outside Fireplace 🔥
Oct 27 – Nov 3
Farm stay in Bonao, Dominican Republic
5.0 out of 5 average rating, 230 reviewsHacienda del Río, Bonao - Casa doña Celia Eco Farm
Oct 31 – Nov 7
Guesthouse in Cabo Rojo, Puerto Rico
4.86 out of 5 average rating, 539 reviewsVilla Vista Puerto
Dec 4 – 11
Apartment in Rincón, Puerto Rico
4.98 out of 5 average rating, 408 reviewsRincón Beachfront Retreat King Master Private Balcony &pools
Jun 27 – Jul 4
Tiny home in Vieques, Puerto Rico
4.97 out of 5 average rating, 200 reviewsVista Mar y Tierra - TinyHouse on acre w oceanview
Nov 11 – 18
House rentals in Caribbean
Home in DO, Dominican Republic
4.92 out of 5 average rating, 300 reviewsBeautifull Guest House with panoramic views
Feb 4 – 11
Home in Sarasota, Florida, US
4.94 out of 5 average rating, 147 reviewsModern, Bright Downtown SRQ A-Frame West of Trail
Jul 3 – 10
Home in Havana, Cuba
4.97 out of 5 average rating, 314 reviewsCasa Colonial 1922-Entire apartment-DATA internet
Mar 24 – 31
Home in Borinquen, Puerto Rico
4.96 out of 5 average rating, 235 reviewsThe Nest at Crash Boat. Only waterfront on Beach
Apr 3 – 10
Home in Playa Tivives, Costa Rica
4.97 out of 5 average rating, 186 reviewsLovely beachfront family house with private pool
Oct 26 – Nov 2
Home in Naples, Florida, US
4.98 out of 5 average rating, 204 reviewsIsland lifestyle family vacation home (Salt Pool)
Aug 12 – 19
Home in Punta Rucia, Dominican Republic
4.99 out of 5 average rating, 141 reviewsVilla Arena - Beach Front
Oct 13 – 20
Home in Rincon, Puerto Rico
4.91 out of 5 average rating, 204 reviewsCasa Ensenada- Rincon Puerto Rico
Sep 26 – Oct 3
Cottage rentals in Caribbean
Cottage in La Romana, Dominican Republic
5.0 out of 5 average rating, 141 reviewsChic Cottage Nature Casa de Campo
May 16 – 23
Cottage in Punta Uva, Costa Rica
4.92 out of 5 average rating, 201 reviewsThe White Cottage, Punta Uva Beach, Costa Rica
Aug 3 – 10
Cottage in San Isidro, Costa Rica
4.92 out of 5 average rating, 129 reviewsCountry house with panoramic view
Jun 15 – 22
Cottage in Ocho Rios, Jamaica
5.0 out of 5 average rating, 412 reviews"Tumbleweed Cottage"
Aug 26 – Sep 2
Cottage in Montego Bay, Jamaica
4.94 out of 5 average rating, 170 reviewsGlory @ Montego Bay
Mar 12 – 19
Cottage in Jarabacoa, Dominican Republic
4.91 out of 5 average rating, 234 reviewsRED DOOR VILLA
Jun 23 – 30
Cottage in Saint Martin , St. Martin
4.89 out of 5 average rating, 170 reviewsBungalow avec jacuzzi vue lagon
Feb 8 – 15
Cottage in San Mateo, Costa Rica
4.95 out of 5 average rating, 215 reviewsLuxury Villa Carao. Jungle Paradise w/Great wifi!
Aug 19 – 26
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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