In the spirit of searching for paradise, you might have given some thought to where to stay in the Caribbean. Whether you’re dreaming of heading off with your special someone for some serious romancing, or you want to go on an adventure with family or friends, there no doubt that a tropical island getaway always hits the spot. Luckily, you’ve come to the right place. In this blog, we’ve rounded up 7 of our most glorious Caribbean villas on three of our favourite islands, Barbados, St Lucia and Jamaica. These luxurious havens are sure to have you longing for some seriously sun-soaked relaxation, and to spark some wanderlust in your travel partners too! 

1. Shangri La, Barbados 

Shangri La – Barbados – Oliver’s Travels

The palm-fringed courtyard at Shangri La will provide you with the perfect welcome to the sun-drenched island of Barbados. Its stunning setting and gorgeous ocean views that can be enjoyed straight from the private swimming pool are complemented by a Colonial period theme and a stunning coral stone fountain. You could easily fall in love with this villa without even taking a step inside, but then you’d miss out on the opulent living spaces, the Crystal Versailles Chandeliers, the french doors that let the sea breeze roll through the interiors, and the modern media room complete with its own cocktail bar. A housekeeper, laundress and cook are available to help you make the most of your stay, and there are local restaurants and bars within walking distance for when you want to explore your surroundings. To say the least, Shangri La is a little slice of Caribbean heaven.

Sleeps: 8

Prices from: £96pppn

2. Cayman Villa, St Lucia

Cayman Villa – St Lucia – Oliver’s Travels

Situated within Cap Estate on Sea Breeze Hills, Cayman Villa is all about luxury and opulence, starting with its gated entrance and the garden that leads up to the colonial-style mansion. In true Caribbean fashion, you can expect high and white timbered ceilings, cool tile floors and solid dark wood furnishings inside. You’ll also be able to enjoy the cinema-style media room, complete with a Sonos sound system. The largest appeal of Cayman Villa, however, is its magnificent outdoor spaces. The villa boasts a fabulous balcony explicitly designed for you to be able to admire the ocean views, as the sun moves through the sky and changes the colours of the island’s tree-clad headland and sparkling sea. These views can also be enjoyed from the lower pool terrace; it’s private infinity pool and luxurious sun loungers. On exceptionally clear days, you’ll be able to see as far as the island of Martinique.

Sleeps: 4-8

Prices from: £143pppn

3. Goat Hill, Jamaica

Goat Hill – Jamaica – Oliver’s Travels

Located in one of Jamaica’s prime locations, Goat Hill was built to make the most of the incredible Caribbean Sea views as well as the most favourable tradewinds during both day and night time. The villa was designed by the son of twentieth-century architect Edward Durell Stone and is made up of an ingenious arrangement of individual pavilions, each wrapped by cut stone terraces and shaded by cedar eaves. The east side of the property captures the sunrise, Montego Bay and the Great River while the west view is a lovely vista toward Round Hill, the Caribbean Sea and sunset. Inside you’ll find chic interior designs, and each bedroom is reached by an exterior stairway, so there is privacy in every living space. Goat Hill also comes with a private chef, so breakfast, lunch and dinner can each be served in different parts of the grounds, at the time of day when they are the most beautiful.

Sleeps: 4-6

Prices from: £137pppn

4. Oceana at Sugar Hill, Barbados

Oceana at Sugar Hill – Barbados – Oliver’s Travels

Oceana sits tucked away amongst tropical trees and is approached via a private driveway, offering perfect privacy and peaceful living on the grounds of the exclusive Sugar Hill. Guests, of course, have access to all that Sugar Hill has to offer, including the clubhouse with its large pool, the restaurant, fully-equipped fitness centre and members lounge, as well as the first class tennis facilities. The villa itself has been beautifully designed with elegantly curved doors, natural wood windows and coral stone walls. Its living room opens out onto a lovely covered terrace through two sets of French windows, where you’ll find the large private pool deck, gardens and view of the sea beyond. Meals can be enjoyed in the partially open-air dining room while looking out to sea from the internal garden. There is even a built-in bar where you can whip up some cocktails as you watch the sunset. 

Sleeps: 6-8

Prices from: £134pppn

5. Colibri Cottage, St Lucia

Colibri Cottage – St Lucia – Oliver’s Travels

The picturesque Colibri Cottage overlooks the sparkling Caribbean Sea where it sits on the St Lucian west coast, surrounded by tropical greenery and flanked by the iconic Petit Piton. Within the villa, you’ll be surrounded by fresh white walls, dark wooden furnishings and pops of colour in traditional Caribbean style. Outside, you’ll find the sunny tropical gardens alive with palm trees, flowers, birds and butterflies. Enjoy meals on the covered dining terrace, where your housekeeper can serve breakfast or lunch daily. With the ocean as your backdrop, you can take swims in the eye-catching infinity pool, which is said to be the longest private pool on the entire island. For guests who prefer swimming in the ocean, the nearest beach is within walking distance of the villa in the direction of Petit Piton. And for adventures further afield, the town of Soufriere is a short drive away. 

Sleeps: 4-12

Prices from: £52pppn

6. Lolita at the Tryall Club, Jamaica

Lolita at the Tryall Club – Jamaica – Oliver’s Travels

Located within the exclusive oceanfront Tryall Club, Lolita is a one-of-a-kind villa, spanning 14,500 square feet and four acres of grounds with breathtaking views of the Caribbean Sea. Designed by Chicago architect Tom Reed, the interiors feature rich mahogany, Italian Travertine and beautiful granite throughout. The villa’s Great Room opens onto a large marble pool terrace, complete with an outdoor dining area and bar, where some of the property’s best ocean views can be found. There is not only one, but two pools at Lolita, including a heated pool for children to play safely in. Inside, guests can enjoy the air-conditioned study with its library of books and movies, and well-equipped gym on the lower level. So that you can enjoy your stay at Lolita to the fullest, the villa also comes with a full staff of a chef, butler, housekeepers, gardeners and laundress.

Sleeps: 6-10

Prices from: £160pppn

7. Windward, Barbados

Windward – Barbados – Oliver’s Travels

Windward rests within a fully enclosed private estate on the stunning west coast of Barbados, yet has full access to the exclusive Sandy Lane Beach Club and all its facilities and amenities. The villa’s open-plan living spaces open up unto a covered veranda via french doors, creating an expansive space for combined indoor/outdoor leisure. From the main veranda, you can step down onto the 1.5-acre tropical gardens where you’ll find the private pool (perfect for cooling off after a session in the professionally equipped gym) and a collection of hidden seating nooks for enjoying the natural surroundings. While there is a formal dining room within the villa, we adore the outdoor dining gazebo, which can be reached via a short covered walkway, and its circular coral stone dining table. Windward also has a team of expert staff available for any assistance you might need during your stay. 

Sleeps: 10

Prices from: £225pppn


If you’re dreaming of the sunny islands of the Caribbean right about now, why not see what else we have to offer in our full portfolio properties in the Caribbean? You may be spoilt for choice, but our friendly concierge team is on hand to help hand pick your perfect Caribbean getaway! Don’t hesitate… paradise awaits. 

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