Distinctive luxury properties for the ultimate trip
Distinctive luxury properties for the ultimate trip
Start-to-finish trip planning
Concierge teams coordinate your arrival, departure, and everything in between.
300+ point inspection
Every Luxury Retreats home is personally verified to be in pristine condition.
On-trip care, 24/7
Premium, on-demand assistance for any question, at any time of day.
1097 luxury villas and vacation rentals in Caribbean
1 – 16 of 300+ Rentals
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Explore luxury vacation rentals in the Caribbean
Are you ready for a change of pace? Luxury Retreats’ villa rentals in the Caribbean allow you to immerse yourself in the laid-back tropical lifestyle of your island of choice, while enjoying the freedom and privacy of your own elegant home.
Ranging from secluded homes to lavish beachfront estates, our carefully selected villas in the Caribbean are perfect for exploring a wide range of destinations, each island boasting its own unique flavor and attractions.
Discover the subdued sophistication of Anguilla or bask in the European flair of St. Martin and St. Barts. Surround yourself in vibrant music and culture in one of our Puerto Rico vacation rentals . Enjoy the breathtaking setting of our Turks and Caicos villas , or the warmth and hospitality of one of many beautiful Barbados vacation rentals . Looking to perfect your golf swing? Our Dominican Republic villas promise a vacation full of beach, pool-side fun and stunning seaside golf action. This is only a taste of the many delightful options for your Caribbean vacation with Luxury Retreats. So, whether you’re looking for an idyllic honeymoon spot, a romantic hideaway for two, or a fun-filled getaway for the whole family, Luxury Retreats has the perfect home for your next Caribbean trip.
Would you prefer a property right on the beach or one tucked away on a quiet hill with breathtaking panoramic views of the sea? Whichever you choose, our Villa Specialists will help you find the luxury villa you need. Many Caribbean villa rentals include a staff of private chef, butler and maid to take care of your every need while you take work on your tan. Private infinity pools are also a regular sight and many Caribbean vacation rentals feature alfresco dining and large terraces from which to enjoy the breathtaking sunsets.
Once you've decided on a destination, our 24/7 Concierge Service will ensure that all the details are taken care of, including car rentals, catering, spa treatments, sailing excursions or just about anything you may desire. All you'll have to do is close your eyes, relax and breathe in the scents of tropical flowers in the breeze...
Experience a luxurious beach vacation in the Caribbean
Should you ever be tempted away from your private oasis, you’ll find there are plenty of ways you can fill your days.
Indulge in some of the Caribbean’s most beautiful beaches
From Harbour Island’s Pink Sands beach to Grace Bay Beach in Turks and Caicos, or Sandy Lane in Barbados, spend a magical getaway just moments away from the silky sands and turquoise surf of the Caribbean's finest beaches. Once there, you can choose to sunbathe on a lounge chair, swim, explore the underwater world, or try a new water sport, be it kayaking, windsurfing, or water skiing.
If you’ve ever wondered what it feels like to swim with sea turtles or stingrays, the Caribbean is just the place for all your snorkeling or scuba diving adventures. Indeed, these warm, crystal clear waters are home to hundreds of species of sea creatures, including brightly colored tropical fish and corals. For spectacular snorkeling and diving spots right off the beach, consider a Luxury Retreats villa stay in St. John, St. Croix, St. Martin, St. Lucia, Virgin Gorda, Antigua, Bonaire or Eleuthera.
Set sail for adventure
Relax with friends and loved ones with something deliciously fruity in your hand and a cool breeze in your hair, as you glide over the dazzling waters of the Caribbean Sea, taking in picturesque shores and tranquil sheltered bays. Fishing enthusiasts will particularly enjoy the bountiful waters around The Bahamas, Turks and Caicos, or the Virgin Islands. The Caribbean offers some of the best fishing in the world after all!
Set your taste buds ablaze with delicious Caribbean cuisine
Sampling local food is an excellent way to soak up different cultures and taste new flavors! Combining fresh ingredients, like straight-off-the-boat seafood, a wide range of spices and far-flung influences, the Caribbean islands serve up some of the world’s most unique and vibrant dishes. Of course, the culinary scene takes different shapes in different places: in St. Barts or Anguilla, you’ll find a sophisticated food scene spanning from upscale neo-Creole cuisine to European fare and Asian fusion, while Jamaica or Puerto Rico’s lively local dishes are more rooted in tradition. Serious foodies should also explore St. Martin, otherwise known as “the culinary capital of the Caribbean”, which is home to over 400 restaurants.
Whether you’re in the mood for a casual beachside grill or opt for a 5-star gourmet restaurant, our concierge team stands ready to ensure you enjoy an unparalleled dining experience. Of course, there is always the option to have your own private chef prepare a tailor-made feast in the comfort and privacy of your villa.
Celebrate Caribbean culture and traditions
Every year, almost every Caribbean island hosts its own carnival or festival, so why not plan a Caribbean vacation to coincide with one of the region’s many celebrations?
From Puerto Rico’s kid-friendly Carnival to St. Lucia’s Friday Night “Jump Up”, Anguilla’s Summer Festival, Junkanoo in the Bahamas, or Crop Over in Barbados, you’ll have more than one opportunity to immerse yourself in authentic island culture. Complete with week-long parades, spectacular costumes, dancing, and delicious street food, the Caribbean’s Carnivals are a feast for the senses, so pack some comfortable shoes and join the party! And when it’s time to enjoy some peace and quiet, what could be better than retreating to the comfort of your own private villa?
It’s time to live the Caribbean dream! Claim a corner of paradise all for yourself with our carefully curated luxury villas in the Caribbean.