The Caribbean has always had a habit of pulling people back. Sometimes it’s the weather in the middle of February. Sometimes it’s the water – that impossible spectrum of turquoise that never quite looks real, even after a week of staring at it. More often, it’s the feeling of island life itself: music drifting out from beach bars, grilled fish arriving straight from the boat, humid evenings that stretch long after dinner.
But the Caribbean never feels exactly the same twice.
Jamaica moves to a completely different beat than St Barths. Antigua revolves around the sea in a way Barbados doesn’t. Anguilla feels slower, quieter, built around long beaches and low-slung hotels, while Bermuda sits slightly apart from the rest of the region altogether – pastel houses, old-school glamour, and Atlantic winds replacing the Caribbean Sea calm found further south.
The hotels follow suit.
Some islands do polished beach clubs and rosé-fuelled afternoons exceptionally well. Others lean more barefoot and outdoorsy, where days are spent sailing, diving, hiking, or at whichever beach everyone seems to have migrated to by sunset. Across the region, though, the best resorts share the same instinct: they understand the island they’re on.
Below, our edit of the Caribbean resorts we return to when we want to properly exhale – from grand old favourites in Barbados to low-key beachfront hideaways in Anguilla, glamorous stays in St Barths, and the sort of hotels in Jamaica where one rum punch somehow turns into three.
Cobbler’s Cove, Barbados
If Barbados still does old-school Caribbean glamour better than almost anywhere, Cobblers Cove might be the island at its most charming.
Set just north of Speightstown on the west coast, the family-run hotel has been around since the 1940s, and thankfully nobody has tried to strip away its personality in favour of minimalist beige interiors or overly serious wellness programming. Instead, you get pink-striped umbrellas, coral stone, rattan everywhere, tropical gardens full of hummingbirds, and the sort of pool you immediately want to spend the next three days beside. The whole place oozes pink appeal in the best possible way.
The suites are surprisingly spacious for a boutique hotel – more old-school Caribbean beach house than slick resort room – with deep verandas, separate sitting areas, and enough wardrobe space to unpack fully. The newer Mile & A Quarter suite, tucked away overlooking the bay, is particularly good for couples wanting something more private.
A huge amount of life at Cobblers revolves around Camelot, the hotel’s long-running seafront restaurant, where lunch regularly drifts into cocktails, and dinner comes with live music a few nights a week. The food leans heavily into local seafood and island produce – flying fish, fresh catch brought in daily, rum punch – while staff greet returning guests by name, remember how you take your coffee, and somehow always know exactly which table you like best. One of the hotel’s loveliest additions in recent years, meanwhile, sits just offshore: floating loungers reached by boat, anchored out in the Caribbean Sea, with cold drinks never too far behind.
Round Hill Hotel & Villas, Jamaica
Round Hill has been part of Jamaican social life for decades. Opened in the 1950s on a private peninsula outside Montego Bay, the hotel still attracts the sort of guests who disappear here for a week every winter.
The Pineapple House rooms, redesigned by Ralph Lauren, lean fully into classic Caribbean style – four-poster beds, white louvred shutters, deep soaking tubs, and wide balconies looking straight out to sea. But the villas are really what people come for. Scattered across the hillside amongst palms and almond trees, many arrive with private pools, outdoor dining terraces, and full staff teams, including cooks preparing breakfast each morning before the beach inevitably calls.
Days at Round Hill move between the infinity pool, the small private beach, tennis courts, and long afternoons spent inside the villas themselves, which feel more like private homes than hotel accommodation. There’s also a newly refreshed spa and wellness space tucked into the gardens.
Despite its long history – JFK and Jackie honeymooned here, Ralph Lauren has holidayed here for years – Round Hill never feels overly polished or self-important. At heart, it still feels like Jamaica: lush, sociable, warm, and impossible to leave quickly.
Rosewood Le Guanahani, St Barths
St Barths has no shortage of beautiful hotels, but Rosewood Le Guanahani has got to be one of our favourites. Glamorous, yes – this is still St Barths after all – but never in an intimidating manner.
Spread across its own private peninsula between Maréchal Bay and Grand Cul-de-Sac Lagoon, the hotel reopened under the Rosewood name in 2021 following an enormous renovation, and the result is perfectly suited to the island: brightly coloured cottages hidden amongst bougainvillaea, sandy pathways leading straight to the water, and a constant balance of French polish and Caribbean ease.
A huge amount of time here ends up around the Beach House – part restaurant, part beach club, part social hub of the hotel – where breakfasts become rosé-fuelled by mid-afternoon and dinners stretch long after the last boats have disappeared from the lagoon. Elsewhere, there’s the island’s largest spa, excellent watersports straight from the beach, and suites with private pools that make leaving your room increasingly unlikely.
What Rosewood Le Guanahani does particularly well, though, is make St Barths feel easy. The island can occasionally tip into being slightly too polished for its own good, but the hotel avoids that entirely. Families pad barefoot to breakfast, couples disappear to beach loungers for the afternoon, and evenings rarely require much more effort than deciding between another cocktail at the bar or dinner somewhere in Gustavia.
As part of the Rosewood Elite programme, our guests also receive a handful of excellent extra perks here, including complimentary breakfast, priority upgrades, hotel credit, and VIP treatment throughout the stay.
Jumby Bay Island, Antigua
Jumby Bay begins with a boat ride. Seven minutes off the coast of Antigua, the resort sits on its own private island where there are no cars, no outside restaurants, and very little reason to think about the real world for a while. Guests get around by bicycle instead – along sandy paths lined with palms, past bougainvillaea-covered villas and some of the whitest beaches anywhere in the Caribbean.
The hotel has long been one of the Caribbean’s great addresses, although nothing about it is showy. Suites open directly onto the sand, villas come with private pools and outdoor showers hidden amongst tropical gardens, and days are wide open for swimming, sailing, tennis, and deciding which beach to disappear to next. Families settle in very quickly, particularly in the larger residences where private chefs and butlers make the entire week run effortlessly.
Food is a huge part of life on the island. The Estate House remains the main event for dinner – all candlelight, seafood, and old plantation-house glamour – while The Beach Shack keeps things far more relaxed with grilled lobster, rosé, and sandy feet very much encouraged. There’s also a very strong wellness offering now, including the recently refreshed spa and a long list of experiences built around the island itself, from coral reef restoration to guided botanical tours.
By day two, guests are cycling between beaches barefoot, abandoning any real sense of time, and seriously discussing whether private-island life might actually be feasible after all.
COMO Parrot Cay, Turks & Caicos
Reached by boat from Providenciales, the private island has been part of the Caribbean luxury conversation for years, although the mood here feels entirely different to somewhere like St Barths or Barbados. There are no beach clubs, no real scene to speak of, and very little temptation to do anything beyond settle into island life as quickly as possible.
COMO’s wellness background runs through the entire resort, but thankfully never in an overly earnest way. Yes, there’s yoga overlooking the water, one of the Caribbean’s best spas, and menus built around the brand’s famous COMO Shambhala cuisine, but there are also enormous beach days, very good margaritas, and villas where most guests seem perfectly content spending half the trip barefoot and horizontal. The resort has also recently expanded its COMO Journeys experiences, including exclusive tennis clinics and wellness-led programming on the island itself.
The accommodation ranges from elegant beachfront rooms to sprawling private residences owned by the likes of Donna Karan and Keith Richards, hidden amongst palms along the shoreline. The newer Beach Houses are particularly good for groups – huge infinity pools, direct beach access, and enough indoor-outdoor living space to make leaving feel increasingly unnecessary by about day three.
Unlike many Caribbean resorts, COMO Parrot Cay never really revolves around a social scene. People come here to read properly, sleep deeply, swim constantly, and briefly forget what day of the week it is.
Six Senses La Sagesse, Grenada
Grenada has always felt slightly separate from the rest of the Caribbean. Greener, quieter, more fragrant somehow – the air thick with nutmeg, cocoa, ginger, and sea salt depending on where you are on the island. Six Senses La Sagesse leans fully into that mood.
Opened in 2024 as the brand’s first Caribbean resort, the hotel sits between the Atlantic Ocean and the Caribbean Sea on Grenada’s south-east coast, spread across rolling hills, lagoons, and two beautifully wild beaches. Like all good Six Senses properties, it manages to be deeply connected to its setting.
The suites and villas are enormous – every single one comes with its own private pool. Mornings here begin with yoga, tennis, or coffee overlooking the lagoon, before shifting towards swims in the sea, rainforest hikes, waterfall trips, or a seriously worth-it spa treatment. The wellness offering is particularly strong even by Six Senses standards, with everything from biohacking and sleep programmes to spice-infused treatments inspired by Grenadian traditions.
Food is another huge part of the experience. SeaFire, the resort’s signature restaurant, revolves around wood-fired cooking and local seafood, while the newer Greens Sushi has quickly become one of the hotel’s most popular additions for lighter lunches and dinners overlooking the water.
As preferred partners of Six Senses, all our guests also receive a handful of excellent extra perks here, including VIP treatment throughout the stay, complimentary breakfast, and priority upgrades whenever available.
Cambridge Beaches Resort & Spa, Bermuda
Bermuda has always done things slightly differently. The beaches are pinker, the sea runs deeper blue, and there’s a slightly old-world mood to the island that feels far more Atlantic than Caribbean. Cambridge Beaches captures that atmosphere perfectly.
Spread across a private peninsula on Bermuda’s western edge, the hotel has been welcoming guests since the 1920s, although a major renovation ahead of its centenary gave the whole place a fresher, lighter feel without losing any of its character. Think pastel cottages scattered amongst palms and frangipani, hidden coves reached by garden pathways, tennis courts ove rlooking the water, and four private beaches where most guests disappear for entire afternoons.
Unlike some of Bermuda’s larger resorts, Cambridge Beaches still feels intimate. Rooms come with private terraces facing the sea, while the newer waterfront suites and pool cottages are particularly good for couples wanting a more secluded stay. The Sunken Harbor Club – the hotel’s excellent cocktail bar from the New York team behind Grand Banks – has also become one of the island’s best spots for drinks, especially once the sun starts dropping over Mangrove Bay.
There’s also plenty happening if you want it – tennis, paddleboarding, sailing, spa treatments inside the oceanfront wellness space.
Cap Juluca, A Belmond Hotel, Anguilla
Cap Juluca sits along Maundays Bay, one of those beaches that genuinely stops people mid-sentence when they first see it. Brilliant white sand, impossibly calm water, and rows of white Greco-Moorish villas stretching along the shoreline like something from a Slim Aarons photograph.
Originally opened in the late 1980s and beautifully restored by Belmond in recent years, the hotel is still one of the Caribbean’s great beach stays – glamorous without becoming showy, polished without losing the laid-back mood Anguilla does so well. Every room faces the sea, many with enormous terraces just steps from the sand, while the private pool villas are well-suited to longer stays.
The biggest recent addition has been the Guerlain Spa, unveiled in 2024 and already finding its way onto global spa lists for very good reason. Treatments draw on local botanicals, salt therapies, and Anguillan influences, while the wider wellness space includes plunge pools, open-air yoga, meditation areas, and one of the prettiest spa courtyards anywhere in the Caribbean.
Cap Juluca also gets the social side of island life exactly right. Lunch at Uchu regularly turns into most of the afternoon, Pimms remains one of the island’s classic dinner spots, and by sunset, the whole resort seems to soften into candlelight, sea air, and the sound of waves rolling onto the shore a few metres away. As one of our favourite Belmond properties – and thanks to our close partnership with the brand – our guests also receive a handful of excellent VIP perks here, including priority upgrades, complimentary breakfast, hotel credit, and extra touches throughout the stay.
Coral Reef Club, Barbados
There’s something wonderfully unchanged about Coral Reef Club. Not in a tired or dated way – more that the hotel seems entirely comfortable in its own skin.
Family-owned since the 1950s, the property sits tucked amongst tropical gardens near Holetown, where pathways weave between coral stone cottages, frangipani trees, and one of the prettiest stretches of Barbados’ west coast. You’re far more likely to find guests dressed for dinner than filming content by the pool, and the atmosphere still carries a distinctly old Barbados glamour that’s becoming harder to find elsewhere on the island.
A huge part of the hotel’s appeal comes from the feeling that everybody already knows one another. Staff greet returning guests like family, afternoon tea still appears daily beneath the trees, and evenings drift between candlelit dinners, live music, and another bottle of wine ordered almost accidentally. The spa, meanwhile, remains one of the island’s best, with colonial-style buildings, open-air treatment rooms, and long stretches of quiet tucked away from the beach entirely.
As preferred partners of Small Luxury Hotels of the World, our guests also receive several excellent VIP privileges here, including complimentary breakfast, upgrades whenever available, and extra touches throughout the stay.
Ready to plan your Caribbean escape?
Whether you’re after a private island in Antigua, old-school glamour in Barbados, or a long week of sea swims and beach clubs in St Barths, we know these islands – and these hotels – exceptionally well.
Through our close partnerships with brands including Rosewood, Belmond, Six Senses, and Small Luxury Hotels of the World, our guests also receive a number of additional VIP privileges throughout their stay, including complimentary breakfasts, upgrades, resort credit, and personalised touches along the way.
Get in touch with our team to start planning your Caribbean escape.
