Caribbean vacation rentals
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Top-rated vacation rentals in Caribbean
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- Entire loft
- Heredia
Insta @ alianzloft. 20 minutes from San Jose airport. First loft built by Alianz.cr. It contains a decked terrace, jacuzzi, firepit, rabbits garden, two rooms, two balconies, entrance gate, private garden, private parking, BBQ area, AC in each bedroom, basketball court, luxury beds, and mountain views. Ideal for architecture lovers, romantic dates, or having a good time. It is a unique space of his kind. Only pets that do not harm rabbits are allowed.
- Entire home
- Sosua
Ultimate 3 bed, 4 bath Vacation Luxury Villa. This house has all the amenities and built for entertaining with TV in every room. Pool Table, Privacy, 24hr security with a beautiful infinity pool & plunge pool with views. If you want an amazing experience this house has it! NO hidden fees, NO cleaning fees, Only 3 minutes to beautiful Sosua Beach, international restaurants and bars, 5 minutes to POP airport and 15 mins to Playa Dorado golf course. This is the best location on the north coast!
- Entire guest suite
- San Juan
Treehouse at La Botanica Hotel + Wellness Center: labotanicahotel.com. You can also find us on IG @ casabotanica_ayurveda, this magical urban oasis has been built in the style of a treehouse, with cream aged wood, polished cement floors, high ceiling, skylights that eye level the magnificent trees in the luscious garden and floating deck with outdoor shower. I also serve a lovely breakfast and yoga in the garden and We have a local store and pop up farm to table dinners Check out our spa!
Popular amenities for Caribbean vacation rentals
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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.
How do I get around Caribbean?
Most of the capital cities in the Caribbean have airports that receive direct flights from the United States, while islands further afield and smaller cities are serviced through connecting flights from Florida. For those wanting to island hop, regional Caribbean airlines will easily take you where you want to go – but if the thought of traveling by prop plane makes you uncomfortable, consider creating your itinerary via ferry. Public boats aren’t always frequent and plentiful, so it may take some planning.
If you’re set on exploring many islands, a combination of flights and ferries is your best bet. Hiring a private boat or yacht to take you between ports is also an option. Taxis are relatively easy to find on the islands. Local buses can be a good alternative and a great way to experience local life, but depending on the island, schedules and information can be ample or limited, so do some research before deciding on your travel routes.
When is 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.
What are the 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.