From La Banane's secluded bungalows to a 400-year-old country estate that was once the home of Perry Henzell, director of the first Jamaican feature film, The Harder They Come...

La Banane, St Barts

In February, La Banane switched from being a boutique hotel to an exclusive villa. It now has nine secluded bungalows strewn amid its tropical grounds, with a gazebo, drinks bar and two palm-shaded pools. Originally founded by Jean-Marie Rivière – a leading figure of the Parisian cabaret world – it continues to exude creative French flair today, with vivid frescos by artist Cyprien Chabert and classic mid-century furniture by Pierre Jeanneret, cousin and lifelong collaborator of Le Corbusier.

La Banane, Baie de Lorient, St Barts (00 590 590 520 300; Weekly rental from US$25,000 (£15,600). Sleeps 18.

Olive Boutique Hotel, Puerto Rico

This characterful hotel was gifted to Loisse Herger and Fernando Dávila by an aunt, as they toasted their wedding day on the Amalfi Coast. The couple honeymooned in Italy, Morocco, Spain and France, before returning to San Juan to restore the property. Now, each floor is dedicated to a different part of their travels, with photos and mementos scattered throughout and earthy, rustic furniture and antiques in each of the 15 rooms.

Olive, Aguadilla St 55, Condado,  Puerto Rico (001 787 705 9994; Suites start at US$260 (£163), including breakfast.

Beach House, Turks and Caicos

This all-suite retreat stands on the pristine sweep of Grace Bay, on Providenciales island. It promises a slice of barefoot luxury, with 21 self-contained suites spread around a shared pool and a long wooden deck that snakes down to the sea. The rooms come complete with a kitchenette for simple self-catering and balconies for dining outside on warm Caribbean nights. Scuba diving, sunset cruises and a private evening meal can be booked as extras.

Beach House, Grace Bay, Providenciales, Turks and Caicos (001 649 946 5800; Suites start at US$532 (£333), self-catering.

Leamington House, Barbados

Leamington House was once the home of the American ambassador, but today is better placed for a group break or family escape. Outside, there are exotic gardens, a small pool and sunbeds. Step within, and a staff team waits to cater for your every whim. Interiors are immaculate throughout, especially in the five pastel-hued bedrooms.  To top it all off, a gate at the bottom of the garden leads straight down to the beach.

Leamington House, Road View,  St Peter, Barbados (001 246 432 0840; Nightly rental starts at US$950 (£595). Sleeps 10.

Bananaquit House, Saint Lucia

Breathe in breathtaking views of the Pitons from the balcony at Bananaquit House. This hilltop haunt stands above Anse Chastanet beach with a veranda that gazes out towards Saint Lucia’s most-photographed peaks. There’s a small pool on the deck, a long table for al fresco dining and five dreamy rooms with beds draped in loose white muslin. The smaller Anse Mamin beach, further north, offers an escape from the crowds.

Bananaquit House, Soufrière, Saint Lucia (Bookings via 020-7581 4643; Weekly rental starts at US$5,000 (£3,125). Sleeps 12.

Itopia, Jamaica

This 400-year-old country estate was once the home of Perry Henzell, director of the first Jamaican feature film, The Harder They Come. Henzell and his family lived in this remote, rambling pile on the island’s north coast for years without electricity. Today, the flickering candlelight may have faded, but all romance is not lost. The villa is now owned by Jakes hotel and retains its quaint, old-world charm with an ivy-clad exterior, crumbling paintwork and metal-frame beds.

Itopia, Runaway Bay, St Ann,  Jamaica (001 876 965 3000; Nightly rental starts at US540 (£338). Sleeps six.