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
Caribbean Beach Vacation Rentals & Luxury Villas
WIMCO Villas has been assisting discerning travelers to the Caribbean islands for over 35 years with their complimentary concierge services and representing a roster of private villa rentals, beachfront vacation homes, and 5 star hotels to choose from.
If you're vacationing with children or with an extended family group, a private villa offers the space and flexibility to tailor vacation days to varied interests. Luxury villa rentals often boast private pools and spacious decks, breathtaking views and proximity to stunning beaches.
Our dedicated travel team will assist with all bookings and travel arrangements from your home to the island of your choice, and our island concierge service will respond to all your needs during your stay.
We will happily book excursions, arrange for spa services or a private driver, hire housekeeping staff or a personal chef, suggest the best beaches and snorkeling destinations, and point you toward local shopping areas, secluded beach bars and fine seafood restaurants. We specialize in personalizing your Caribbean villa vacation to meet your individual expectations.
Great Caribbean Islands to Visit on Vacation
Each Caribbean island has a different "flavor," and our vacation planners will help you decide which one to visit based on your interests and preferences. Because we personally visit each of our vacation villas, we can anticipate your questions and help you select the perfect island and villa for your vacation.
We will be happy to discuss not only the character and amenities available on each Caribbean island, and the specific advantages of each private villa that's available to rent.
Wonderfully welcoming options exist: Pick a sparsely populated sand bar as your private paradise or choose a mountainous, volcanic "rock" in the sea to assure that your inner explorer will be satisfied. In either case, your home base can be a luxury Caribbean villa rental.
Some islands have quaint historic towns full of European flair, like Gustavia in St Barths, Philipsberg in St Martin, Cruz Bay in St John, with 5 star resort hotels, pampering spas, fine restaurants, tropical gardens and expensive shops. Others offer only pristine beaches, the occasional beach bar, and private villas, a scene that encourages total relaxation.
Caribbean islands are strung like pearls on a necklace, each one unique. Enjoy the surf, bask in the sunshine, sample native foods and experience the beauty of extraordinary sunrises and sunsets on almost every island.
Walk for miles along a secluded beach, hike island paths, visit a rum factory, buy native handicrafts, and sample local foods. Or just settle into one of our luxury vacation rentals in the Caribbean and relax. It's all up to you.
Renting Luxury Villas or Luxury Resorts - Which One Is Right for You?
At WIMCO Villas, we understand that some travelers prefer the services and distinctive comforts offered by 5 star luxury resort hotels. If on-site services and upscale amenities are your choice, we'll be happy to book reservations for you at one of the exceptional island resorts that dot Caribbean islands. Friends traveling together sometimes prefer the flexibility and convenience epitomized by such a choice.
However, if you're traveling with a family group, or prefer a less-structured, more personalized vacation where dress codes or schedules won’t interfere with your own tropical rhythms, we'll tailor luxury villa rentals to fulfill those dreams. You can be sure that personalized services are available to meet your every request, whether for a fully-staffed villa, a local car rental, or a complete list of the best beach bars.
Most vacation villas on Caribbean islands boast modern features, with spacious rooms, large decks or patios and stunning ocean views. They are equipped with all the convenience of your own home - comfortable beds, private bathrooms, well-equipped kitchens, audio/visual entertainment systems, and washers and dryers.
You'll be close to white sand beaches, water sports, and fresh-caught seafood that you can prepare at your luxury vacation rental or eat in local restaurants. The Caribbean is truly an ideal vacation getaway.
Legendary Caribbean islands also have legendary luxury resort hotels. They're frequently featured in slick travel magazines and frequented by celebrities and royalty. These five star hotels offer the ultimate in spa services, beautifully landscaped grounds, onsite recreation, restaurants and entertainment, and personal services. WIMCO’s reservations department can describe each to you, and secure preferred terms for the one you choose to book.
Some of the more renowned luxury vacation resorts we represent include Belmond Cap Juluca and the Four Seasons Viceroy on Anguilla, the Belmond La Samanna Resort, St. Martin, Round Hill Montego Bay Resort in Jamaica, secluded Parrot Cay and Amanyara in the Turks and Caicos, Sandy Lane in Barbados, Little Dix Bay on Virgin Gorda in the British Virgin Islands, and Le Sereno Hotel & Spa on the island of St. Barts.
Interested in booking a Caribbean hotel for your vacation? Contact WIMCO's Hotel Reservations Desk.
Villas Available during Holidays or School Break in the Caribbean
While family vacations in the Caribbean are a wonderful choice for families any time of year, a vacation at holiday time or a week-long stay during a school vacation - especially in the winter when the weather at home can be frightful - is particularly appealing.
Renting a luxury beachfront villa for Christmas or New Year's is a memorable gift for the entire family, but a week-long stay in an island paradise is a long-to-be-remembered treat at Thanksgiving, a welcome break from routine between semesters in February, or great fun for a Spring break trip.
Several islands have seasonal celebrations, and a WIMCO Villas vacation planner will help you plan a trip to correspond to a local event, perhaps a sailing regatta or an island version of "Carnivale," an independence celebration or a unique way to teach the kids about different customs and native traditions.
However, remember that vacations during holidays and special events should be booked as far in advance as possible. Available luxury villas tend to be in high demand in peak season. Contact us early to begin planning your island vacation.
Traveling during a School Break?
How to Get to the Caribbean Islands
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.
Where Are the Most Beautiful Beaches in the Caribbean?
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.
When Is the Best Time to Vacation in the Caribbean?
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 Events & Festivals
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.
Traveling for an Event?
What Are the Best Things to Do in the Caribbean?
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.
What Services Does WIMCO Villas Provide to Our Clients Vacationing in the Caribbean?
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.