In the spirit of this search for paradise, we’ve picked 10 of the most glorious Caribbean villas. Whether you’re dreaming of heading off with someone special for some serious romancing (bound to be worth several thousand brownie points), chilling with a few close friends or even on your own, these properties are sure to have you longing for some seriously sun-soaked relaxation.

1. Capri Manor, Barbados

Capri Manor - Barbados - Oliver's Travels

Capri Manor – Barbados – Oliver’s Travels

This villa is perfect for a family getaway, with its beautiful king-size bedroom suites, Jacuzzi and a full family sized swimming pool. However, if you fancy a slightly longer swim the property is just across the street from the world famous Gibbs Beach in Barbados. Now that’s a real slice of paradise.

Sleeps: 8

Prices from: £88pppn

2. Sea Haven on Discovery Bay, Jamaica 

Sea Haven on Discovery Bay - Jamaica - Oliver's Travels

Sea Haven on Discovery Bay – Jamaica – Oliver’s Travels

Located on a private waterfront acre, Sea Haven is a miracle of Caribbean colour. From its blue exterior to the sunshine yellow inside, you’ll be constantly walking with a pep in your step. Apart from the four fully airconditioned bedrooms, other rooms in the villa include a living room, formal dining room and kitchen. Then there’s the garden, which makes me the most tropical escape, smothered in orchids and trees. So, get the bottle of rum at the ready and enjoy all Sea Haven has to offer.

Sleeps: 4-8

Prices from: £60pppn

Tamarind House, St Lucia

Villa Tamarind - St Lucia - Oliver's Travels

Villa Tamarind – St Lucia – Oliver’s Travels

Tamarind house is the place of dreams. With a tennis court looking out to the most beautiful ocean view, a stunning infinity pool and your own personal cook and maid you’ll be living the life of luxury. The open plan design allows you to enjoy the Caribbean breeze in the evening with long white curtains blowing in the wind. Or, if you’d prefer, you can dine under the Tamarind tree in the picturesque courtyard.

Sleeps: 4-6

Prices from: £73pppn

Shangri La, Barbados 

Shangri La - Barbados - Oliver's Travels

Shangri La – Barbados – Oliver’s Travels

The sweeping, fern-fringed drive up to Shangri La is breathtaking. Once you arrive, you’ll be greeted by panoramic ocean views and stunning scenery. If you don’t want to spend all of your time on the famous beaches, it has a wonderful courtyard, pool and its own bar where you can unwind during the day. The patio in the evening is a stunning place to dine as you can enjoy the star-filled skies that the Caribbean has to offer. 

Sleeps: 8

Prices from: £93pppn

Oceana at Sugar Hill, Barbados

Oceana at Sugar Hill - Barbados - Oliver's Travels where to stay in the caribbean

Oceana at Sugar Hill – Barbados – Oliver’s Travels

Overlooking the Caribbean Sea, Oceana is a magnificent villa located in the exclusive gated community of Sugar Hill. Oceana maximises the benefits of its superb position with the enjoyment of tropical living. This is truly the perfect place for cocktails as you watch the sunset over the sea.

Sleeps: 8

Prices from: £135pppn

Villa Tonelero, Barbados

Villa Tonelero - Barbados - Oliver's Travels

Villa Tonelero – Barbados – Oliver’s Travels

Relax on any one of the beautiful terraces and enjoy views over the 1.5-acre tropical gardens, or walk around and discover the many secret seating areas where you can hide away in this natural paradise. Plus there’s an incredible team of professional staff are on hand to assist with anything you may need.

Sleeps: 10

Prices from: £225pppn

Goat Hill, Jamaica

Goat Hill - Jamaica - Oliver's Travels

Goat Hill – Jamaica – Oliver’s Travels

Goat Hill is an uber-luxe property carved into a tropical landscape! The panoramic views out over the island are perfect for watching the sunset from the chic infinity pool.  With stone terraces and lavish interiors, this property is dripping with exclusivity, Goat Hill is luxury at its finest.

Sleeps: 4-6

Prices from: £271pppn

 Greatview, Jamaica

Greatview - Jamaica - Oliver's Travels

Greatview – Jamaica – Oliver’s Travels

Greatview is a slice of paradise set on the sunny island of Jamaica. At the back of the house is a super stylish infinity pool overlooking the blue waters of the Carribean sea. One of its most striking features is the covered terrace, perfect for meals in the tropical heat. Within the tourism capital of Montego Bay, there’s plenty to do nearby from The Rocklands Feeding Station to an array of tasty local restaurants!

Sleeps: 6-12

Prices from: £96pppn

Caille Blanc, St Lucia 

Caille Blanc - St Lucia - Oliver's Travels

Caille Blanc – St Lucia – Oliver’s Travels

This incredible 6 bedroom home comes complete with a 65-foot infinity pool. The waterfall facing the sea under a breathtaking backdrop of the majestic Pitons is nothing but dreamy. To top it off, this outstanding haven is within a few minutes drive to the pristine Anse Chastanet Beach – so don’t forget your beach towel!

Sleeps: 4-12

Prices from: £168pppn

Lolita at the Tryall Club, Jamaica

Lolita - Jamaica - Oliver's Travels

Lolita – Jamaica – Oliver’s Travels

Lolita is a villa that oozes sophistication. Facing out to stunning views of the deep blue Caribbean Sea this villa really makes the most of its impressive vistas from a luxurious infinity pool, patio and outdoor bar and dining area. It is surrounded by four acres and has a swanky contemporary interior for you to relax in. Equipped with plenty of outdoor activities, and even a helicopter pad, you will never run out of things to do on your luxurious escape in this award-winning villa.

Sleeps: 6-10

Prices from: £153pppn


It’s inevitable that you’re dreaming of the sunny islands now. Why not see what else we have to offer on our full list of 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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