Luxury in the Caribbean

The Caribbean consists of a number of countries known for their slowed-down way of life and natural beauty, ranging from the Dominican Republic to the Virgin Islands to Jamaica to St. Barthelemy. If you're in the market for a luxury vacation at a spectacular oceanfront villa, HomeAway is sure to have you covered.

U.S. Virgin Islands

Split into four main U.S. territories, the U.S. Virgin Islands comprise an archipelago, or island chain, filled with picturesque locales. One of the most popular islands among visitors is St. John.

Explore all 12,500 acres of Virgin Islands National Park, which encompasses two-thirds of the island. With coral reefs magnificent for snorkeling and scuba diving, shorelines meant for curious bare feet and tropical vegetation as far as the eye can see, this place is truly a nature lover’s wonderland. It is complete with 22 trails, Danish colonial sugar plantation ruins and Cinnamon Bay, where you can rent sailboats and kayaks.

Trunk Bay is the Caribbean beach that all Americans daydream about. It has pearly sand and aquamarine water, so you won’t be disappointed. Don’t forget to check out the Underwater Trail for a snorkeling path filled with fish, coral, and underwater plaques. Watermelon Cay within Leinster Bay is another knockout. Dive beneath the waves to catch a glimpse of stingrays, Hawksbill turtles and even baby barracuda.

US Virgin Islands luxury rentals

Dominican Republic

Sharing the island of Hispaniola with Haiti, the Dominican Republic is a Spanish-speaking country famous for hosting the Duarte Peak, which is the highest point (at 10,417 feet) in the West Indies. The scuba diving continues in the warm waters of the Southern Coast in the Dominican Republic. They feature package deals with professional instructors to gaze at amazing marine life on an subsurface adventure.

Cigar-lovers, meet your maker. At La Aurora Cigar Factory in Santiago, you’ll be feeling on top of the world with these fatties in your hand. If you enjoy smoking a complex, rich cigar with flavors that last until the finish, this spot is not be missed. Reservations are recommended. Take a horseback riding tour at Rudy’s Rancho in the small fishing hub of Las Galeras. You’ll venture on a scenic path between coconut trees along the sea. Discover flora and fauna while meeting the locals. Waterfalls, rivers and jungles are all waiting to be explored.

Dominican Republic luxury rentals

Jamaica

Encounter 635 miles of coastline, rugged cliffs and welcoming locals. Even though the official national language is English, you’ll generally hear Jamaican Patois, which is a Creole of English and African. At the Blue Hole in Ocho Rios, you can experience the hidden treasure of an exhilarating waterfall. Unbeknownst to the swaths of mainstream tourists, this blue mineral pool leads in and out of caves, around cliffs and off edges. You and your friends can leap off the rope swing at this jungle adventure, or hike around the falls with local guides.

A slice of natural wonder comes with territory at Blue Mountains National Park in Kingston. Located on the eastern edge of the country, the Blue Mountains lend themselves to half or full-day trips for the avid hiker. Trails and terrain are strenuous but well worth it, as the peak reaches 7,402 feet. If that sounds a bit too extreme, sit back, relax and sip on the region’s famous Blue Mountain coffee. Head to Negril Cliffs for an idyllic snapshot of where the cliffs meet the sea. The divers may impress you for a small tip, otherwise you can get your adrenaline pumping and jump off the rocks, some of which are up to 50 feet high. To loosen up beforehand, though, make your way to Rick’s Cafe for tasty cocktails.

Jamaica luxury vacation rentals

St. Barthelemy

St. Barthelemy, also known as St. Barts, was named after Christopher Columbus’ brother Bartolomeo in 1493. Today, it serves as a home-away-from-home for a handful of celebrity titans, including Beyoncé, Jay-Z, Harrison Ford and Paul McCartney. Shop till you drop along the streets of Gustavia, St. Barts’ capital. Quai de la Republique Street is a good one, where you’ll find everything from Gaultier to plastic sunglasses in boutiques and local stores. The neighborhood also boasts a wide selection of restaurants to sip wine and soak in the luxury living amidst the red-roofed paradise.

Surfing and windsurfing are popular on several beaches in St. Barts, from Lorient to Anse des Cayes to Toiny. If you’ve never tried, there are specialty shops that provide rentals as well as handsome and helpful local guides for your first ride. To keep your senses sharp on vacation, be sure to visit the country’s historic sites of Fort Gustav and the Wall House Museum in Gustavia. At the fort, you’ll see the ruins of an 18th century fortification packed with stone ramparts, cannons and a powder house. It is also one of the best vantage points to enjoy views of the harbor. The Wall House Museum features historical engravings, texts and maps that follow the history of Columbus to the Swedes and more.

St. Barthelemy luxury rentals

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