Strawberry Hill, Jamaica
Part of Chris Blackwell's Island Outpost portfolio of Jamaican retreats, Strawberry Hill is the only "outpost" set inland. The former 18th-century coffee plantation resides in the Blue Mountains with dramatic views of the shore 3,100ft below. The Georgian-style cottages are decked out with four poster beds and rattan rugs, and are surrounded by secondary forest, coffee plantations and well-established gardens.
Strawberry Hill, Irish Town, St Andrew, Jamaica (001 876 944 8400; islandoutpost.com/strawberry_hill ). Doubles start at US$231 (£150), including breakfast.
Sugar Ridge, Antigua
The best way to appreciate the dazzling peacock hues of the Antiguan coastline is from above. The recently opened Sugar Ridge hotel on the island's west coast offers just such an opportunity from its elevated hillside location, surrounded by emerald green sugar cane fields. Rooms are elegant and breezy and come with either spacious verandas or plunge pools. The infinity pool and restaurant overlook forested ridges and the sea, there's a shuttle down to the beach and forest canopy tours nearby.
Sugar Ridge, Jolly Harbour, Antigua (001 268 562 7700; sugarridgeantigua.com ). Doubles start at US$202 (£135), including breakfast.
Montpelier Plantation, Nevis
An 18th-century sugar plantation that hosted the wedding of Admiral Lord Nelson and Fanny Nisbet provides the setting for this elegant lodge. Set at the foot of the volcanic Nevis Peak, Montpelier Plantation's whitewashed cottages belie sleek, contemporary interiors. However, most rooms don't feature phones, TVs or internet – this is essentially a get-away-from-it-all retreat. Instead, opt for a dip in the pool, read a book in the gardens or explore the surrounding countryside on foot or horseback.
Montpelier Plantation, Charlestown, Nevis (001 869 469 3462; montpeliernevis.com ). Doubles start at US$384 (£256), room only.
Hix Island house, Puerto Rico
The striking concrete architecture of this retreat contrasts with the lush vegetation that surrounds it. Four buildings house a collection of loft apartments that take inspiration from the granite boulders that are scattered around Vieques island.
Hix Island House, Vieques, Puerto Rico (001 787 741 2302; hixislandhouse.com ). Doubles start at US$203 (£135), with breakfast.
Casa Bonita, Dominican Republic
Set next to the tropical highlands of the Bahoruco National Park, Casa Bonita is in the unspoilt south west of the country. The cabana style rooms sit on a forested hill overlooking the Caribbean Sea.
Casa Bonita, Bahoruco, Barahona, Dominican Republic (001 809 476 5059; casabonitadr.com ). Doubles start at US$164 (£109), B&B.
Ladera, St Lucia
This dramatic retreat clings to a mountainside on a former cocoa plantation. Villas and suites feature an open-sided wall to bring in the verdant view, plus plunge pools from which to take it in. Hiking and birdwatching opportunities abound on the doorstep.
Ladera, Soufrière, St Lucia (001 758 459 6600; ladera.com ). Doubles start at US$448 (£299), including breakfast and afternoon tea.