With so many stunning Caribbean islands to choose from, deciding where to begin your luxury Caribbean getaway can feel overwhelming. But rest assured, we’re here to guide you with our curated collection of villas in the Caribbean. Whether you’re seeking an action-packed adventure, a romantic escape with your special someone, or a memorable family vacation, there’s an island perfectly suited to your needs. Browse our curated list of the top 10 Caribbean islands, find the one that speaks to you, and let the booking begin!
1. St. Lucia
St Lucia means one thing – luxury! Whether you’re looking for a honeymoon that pulls out all the stops or the kind of holiday where your every whim is catered for, St Lucia has the facilities – not to mention the achingly beautiful villas – to make it happen. If you’re looking for adventure, try climbing the iconic Pitons, heading into the Chassin rainforest or enjoying some of the world’s best diving. The island’s musical pedigree also means there’s loads to choose from if you fancy a night on the tiles…
Best for: Adventure holidays, romantic honeymoons, spas, and pampering.
2. Barbados
If you like your holidays full of adrenaline and adventure, this is the one for you. The huge swathes of beautiful natural parks on Barbados are ideal for exploration, while the lively waters are perfect for surfing. Better yet, there’s some varied and spectacular food on offer – everything from tasty street food to high-end dining. The capital of Bridgetown and the island’s many towns love to party, so if you’re after a fun-filled holiday in the Caribbean sun or a honeymoon that’s all about the nightlife, you can’t pick a better spot.
Best for: Shopping, non-stop holidays, and nightlife.
3. Jamaica
Big on food and big on flavour, Jamaica’s full of music, life and rhythm. Great if you’re looking for a resort-style holiday and want to spend your time in the thick of the action, living life to the fullest. As the home of reggae and jerk seasoning, you know everything in Jamaica is going to be big and bold, from the beautiful beaches to the Blue Mountain national park, where you’ll find waterfalls and walking trails straight out of some tropical dream. It’s also your ideal island pick if golf is your holiday recreation of choice, with plenty of courses to keep golfers of all abilities happy.
Best for: Food and drink, music and nightlife, and exciting honeymoons.
4. Grenada
Grenada’s got pretty much everything the Caribbean has to offer. Make the most of the romantic scenery by hiking in the rainforest, swimming in waterfalls, or just driving around, taking in the amazing views and wildlife. With such wonderful ingredients, the food is superb, and hanging out with the locals is a clear highlight. Grenada’s beaches are idyllic, scattered with bars and restaurants and launches for some unforgettable sailing and diving. It’s also the gateway to sleepy sister islands Carriacou and Petite Martinique, which become pretty lively during festivals.
Best for: Scuba diving, food, and history.
5. Antigua
One of the undeniable highlights of Antigua is its abundance of stunning beaches. Whether you want cocktails for newlyweds on the shore, paddling with the kids in shallow, turquoise coves or diving down into the depths with your trusty scuba gear, Antigua’s gorgeous coastline has you covered. The island also has a fascinating and turbulent history to explore, so be sure to take time out of your sun-worshipping to stroll around and learn a thing or two about the intertwining histories of Europe and the Caribbean.
Best for: Architecture, history, and hidden coves.
6. Turks & Caicos
This impossibly turquoise string of islands and cays is a big draw for honeymooners and adventure travellers alike. The tiny British Overseas Territory comprises pretty colonial towns, stunning natural wonders, dive sites, awesome shipwrecks, and much much more. You may even be lucky enough to spot humpback whales that travel through the shallow waters of the TCIs during their migration. Stunning!
Best for: Island hopping, whale and dolphin spotting, and seafood.
7. Dominican Republic
The Dominican Republic offers a landscape of huge contrasts, from golden white sand beaches and clear blue seas to inland rainforests and waterfalls – not to mention the deserts, lakes and mountains. The list of things to do is exhaustive. Get your culture fix by learning the merengue, exploring colonial streets and buildings, or sampling the amazing local food and art. Out of town, you can play on one of many championship golf courses, scuba dive, go whale-watching, windsurfing, fishing or sailing. For the eco-conscious, there are some stunning areas of natural beauty and nature parks, too!
Best for: Nature, watersports, and golf.
8. St. Barts
If you like to be seen in the right place (or want to catch those that are), then this is the island for you. St Bart’s is known for its chic islanders, French sophistication and exclusivity. There’s a burgeoning art scene for culture vultures, high-end restaurants for foodies, incredible beaches, and superb spas for unwinding. For the more active, there’s bird-watching or you can explore neighbouring islands by boat. There’s an abundance of high-end options in just about everything – from haute couture to beach-side villas – meaning that it’s great for a honeymoon if you really want to show your other half how much you care.
Best for: Glamour and über luxury, high-end food and drink, and perfect white beaches.
9. Tobago
A true tropical paradise, Tobago is neatly split into a bevvy of beautiful beaches on its western side with a dense, expansive rainforest (the oldest protected one in the world!) on the east. This means you’re sorted for trekking through miles of unspoilt foliage and maybe even a dip beneath a tropical waterfall. Tobago is also particularly famed for its diving thanks to some stunning coral reefs and sunken wrecks, and there’s an abundance of fun things to do, including traditional Easter goat racing and an eclectic mix of festivals, including the annual Jazz festival in April.
Best for: Exploring luscious rainforest, scuba diving, boat trips and fishing.
10. Anguilla
It’s got less mass tourism than some of the other islands, and thanks to the beautiful coastline, it’s perfect if you’re into watersports – diving and sailing ahoy! The Anguillan locals are as warm and welcoming as the weather, and the sumptuous holiday villas on offer mean you’ll be able to enjoy the palm-fronted and pristine white beaches in the lap of luxury. Because cruise ships aren’t allowed to dock, there are markedly fewer crowds – great for a fantastic honeymoon or romantic break where you can feel like the island is all yours.
Best for: Food and fine dining, romantic breaks, snorkelling, and carnival.
Decided which of our top 10 Caribbean islands you’d like to visit? Now, you just need to figure out when to book your idyllic island escape. Between February and April, many of the islands host their annual carnivals – colourful celebrations involving music, dance, street food, and more. Visit during these months to see the islands at their most vibrant.
Check out our full portfolio of villa holidays on Oliver’s Travels, and contact our friendly concierge team to ask any questions!
