Caribbean Villas & Luxury Vacation Rentals

The Caribbean islands are a favored vacation destination for visitors from across the globe, primarily because of consistently warm weather, beautiful ocean views, serene beaches and interesting cultural historical sites. 

The diversity of the islands is, however, what can make choosing a specific island for a stay of a week or longer a fascinating challenge. Spacious beach front villas, luxury resort hotels, and distinctive beach rentals are available on islands large and small. 

Luckily, whether you want a "toes in the sand" kind of vacation or an upscale dive into island food, music and culture, there's sure to be a Caribbean Island that is an ideal fit for you.

Top Caribbean Vacation Destinations

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Caribbean FAQ's

Getting to the Caribbean from most cities in the United States and Canada is easy. Major Airlines, including American, Delta, United, Jet Blue, Alaska Airlines, Southwest Airlines and Air Canada fly direct to Caribbean destinations from dozens of cities in both countries including New York, Chicago, Boston, Charlotte, Atlanta, Miami, Dallas, Houston and Washington DC. Visitors will have little trouble finding flights to San Juan PR, St. Martin, Providenciales in the Turks and Caicos, Barbados, Jamaica, Grand Cayman and the Dominican Republic. Many exceptional smaller islands have airports that can only accommodate smaller planes, or ferries so when visiting Anguilla, St John, St Barts, Mustique, Canouan, Virgin Gorda and other gems, you’ll need to book an inter-island connecting flight. For US citizens traveling to the U.S. Virgin Islands or Puerto Rico is considered a domestic flight, so no passport is required. However for the rest of the Caribbean islands you’ll want to have a passport in hand that is valid for at least six months from the arrival date. For residents of countries in North America and the European Union, visas are not typically required for vacation visits to Caribbean islands.

Although every visitor finds they have their own favorite beach - and the reasons differ from one person to the next – it's clear that the sand and sea of the Caribbean combine to offer visitors a rare treat. Several island beaches repeatedly make the lists of "World's Best Beaches” in publications like Travel & Leisure and Conde Nast Traveler. Our vacation planners will share their favorites, however almost everyone agrees that these five are among the best: Grace Bay Beach, Turks and Caicos: One of the most beautiful bays - and longest beaches - in the whole of the Caribbean, Grace Bay is home to extraordinary luxury vacation rentals, lively beach bars, fine restaurants, and an expanse of white sand beach that is envied the world over. Shoal Bay East, Anguilla: With water that ranges from clear turquoise to deep cobalt, a large coral reef just off shore, and a dozen fun restaurants, this stretch of white sand beach consistently awes visitors Seven Mile Beach, Grand Cayman: A large part of the appeal of this coral sand beach is the lively ambience of the beach bars and eateries that exist in harmony with nature. Enjoy strolling the length of the beach - it's really only about 5 1/2 miles. Plan to snorkel or scuba dive nearby or go parasailing. It's all there. The Baths, Virgin Gorda: This is actually a collection of secret pocket beaches separated by house sized boulders. Once you've experienced The Baths of Virgin Gorda, nothing else quite compares! Suffice it to say that you'll want to return again and again to walk among the boulders, marvel at the rock formations, and experience the wonder of the underwater caves and pristine pocket beaches. It's spectacular. St. Jean Beach, St. Barts: A perfect day can include swimming and sailing in the bay’s warm waters, dining with your feet in the sand at one of its celebrated beach bars like Nikki Beach or Pearl Beach, and watching the small prop planes take off and land at the nearby airport. It's one of those picture-postcard worthy settings that the whole family will love.

Caribbean islands have an almost perfect location, with a sunny, tropical climate all year long. Depending on the specific location of the island you choose to visit, temperatures can vary from the mid-70s to the upper 90s, but prevailing winds provide comfort from the heat.

The water and beaches, of course, are the big draw for tourists. The most popular time to visit is November through June with peak season being the winter months when an island vacation is a great way to escape the cold and snow up north. Let WIMCO Villas vacation planners help you plan your stay at a luxury island villa on one of the beautiful Caribbean islands.

Caribbean islands were claimed and colonized by the French, English, Dutch, and Spanish; their diverse cultures merged with the traditions of indigenous cultures and contribute to the patchwork quilt appeal of various island traditions to this day. If you're interested in visiting a specific island to experience a unique celebration, ask the advice of one of our vacation planners. Barbados has a Celtic Celebration, while Anguilla residents honor their unique heritage on May 30 for Anguilla Day and host a yacht festival, a literary "jollification" and a yacht festival the same month. It's a happening place. If you're a dedicated "foodie," plan to visit the Cayman Islands during one of its food festivals.

Only you can answer that, but we at WIMCO Villas can be your guide. From lazy days on the beach to a deep sea fishing trip, from a parasailing "flight" to a hike to the rim of an extinct volcano, from scuba diving at the site of a sunken Spanish galleon to snorkeling along the third largest barrier reef in the world, some of the best adventures to be found on earth happen in the Caribbean. We at WIMCO Villas are here to make your dreams come true, whether you choose a 5 star luxury resort vacation or a secluded luxury rental villa for a family reunion. We will also help you plan a destination wedding or a corporate seminar at a private island.

If you are looking for the perfect, carefree Caribbean vacation, all by making one call and having everything taken care of, we have you covered. The knowledgeable and friendly staff at WIMCO Villas will not only make arrangements for your luxury Caribbean villa or five-star resort, but will also handle booking all of your travel logistics. All this for no additional cost.


Want your refrigerator stocked when you arrive? Let us know what you want to drink and eat, and we'll make it happen. Want breakfast on the beach at your vacation villa? We will make that happen too. What about a beachside table for that anniversary dinner? You got it!


It is our mission to do whatever it takes to make your vacation memorable and enjoyable. Imagine getting vacation and accommodation tips from a close, trusted friend who has traveled everywhere you dream of going. WIMCO Villas' travel specialists are like that, but even better. How, you ask? Well, our team and local representatives have not only visited each property, but they know the surrounding area well.


They know the right questions to ask so they can best assist you in selecting the vacation rental that best meets your individual wants, needs and desires. Feel free to contact us and start planning that Caribbean dream vacation you have been thinking about.