Exterior view of the Rockhouse Hotel

Island Living is Good at These Jamaica Hotels

This tropical, soulful island has earned its place as one of the Caribbean’s most popular getaways thanks to standout cuisine, a rich musical history, and stylish beachfront hotels.

Senior Editor, Jetsetter | @lindseytravels | lindseytravels.com

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View of forest from Strawberry Hill
Bar at Strawberry Hill
Exterior view of Strawberry Hill

Strawberry Hill

Does this hotel have the best pool in Jamaica? We’ll let you decide: its infinity edge reaches right out over a mountainside, where a sweeping view of Kingston spreads out below. Record producer Chris Blackwell (also behind The Caves in Negril and GoldenEye in Oracabessa) modeled everything at this 13-room reprieve after the colonial Jamaica of the 19th century, with Georgian-style timber cottages that retain colonial charm—plantation shutters, mahogany four-poster beds, private verandas overlooking the misty mountainside. Blackwell is the reason why this spot has secured a place in music industry lore (Bob Marley, Sting, and Mick Jagger have all stayed). Check out the Gold Room to see records and awards for Blackwell’s work with greats like U2 and Bob Dylan.

Beach at Jamaica Inn
Hammock on the beach at Jamaica Inn
Lobby at Jamaica Inn

Jamaica Inn

The Fifties have been in vogue at the family-owned Jamaica Inn since it opened in 1950 on a private cove east of Ocho Rios. Here, the retro and traditional come together with the kind of old-time glamour that has attracted the likes of Marilyn Monroe and Error Flynn. You won’t find TVs or alarm clocks in any of the 50 white-on-white guest rooms, which are done up with chic colonial furniture and plantation shutters. This place is all about embodying a laidback lifestyle (without the latest tech gadgets). Our favorite amenities are the waterfront spa, live reggae, and the private white-sand beach. If you're a honeymooner, spring for the cottages, which come with their own pools and direct ocean access.

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Grounds Hotels Luxury Outdoor Activities Resort Romantic Tropical Waterfront tree outdoor water leisure Boat amusement park Water park swimming pool River park Lake bridge swimming surrounded

GoldenEye Hotel & Resort

The name of this Caribbean-chic estate is no accident—Ian Fleming, author of the 007 series, once owned this tropical playground, where he penned all 14 James Bond novels. A swim-up spa, treetop restaurant, and menu of water sports are new—and welcome—additions, but his original three-bedroom holiday villa still stands, where creative types can while away their vacation in the presence of Fleming’s desk, carved from Jamaican red bulletwood. Not that the other accommodations are any less sexy: think clawfoot tubs, bright lounges, and outdoor showers, all lining a white-sand beach littered with banyan and mango trees and fronting a green lagoon.

Exterior view of Trident Hotel
Living room at Trident Hotel
Lounge chairs overlooking the ocean at Trident Hotel

Trident Hotel

Despite opening in 2013, the Trident Hotel feels right at home in Port Antonio. Eye-popping modern art pieces make a serious statement in the otherwise all-white spaces of each freestanding villa, which are also kitted out with their own terrace, steam room, outdoor bath, and heated plunge pool. Drag yourself away from those picture-perfect views of the Caribbean and head to the Harlem-inspired, speakeasy-style Mike’s Supper Club, where Jamaican and Japanese cuisine is served while vocalists are accompanied by a beat-red 1917 Steinway piano. The best part? Guests share facilities with Trident’s sister property next door, Trident Castle, which has hosted the likes of Audrey Hepburn and Johnny Depp.

Bedroom at Rockhouse Hotel
Pool at Rockhouse Hotel
Ocean around Rockhouse Hotel
Aerial view of the pool at Rockhouse Hotel

Rockhouse Hotel

One glance and you’ll understand why they named this serene 34-room escape “Rockhouse”: hexagonal buildings made from cut stone rise up from the limestone cliffs along Negril’s West End, where stairs and walkways are carved right into the bedrock for easy navigating of the property’s gardens, restaurant and rum bar, spa pavilion, and jumping-off points into the turquoise Caribbean. Rooms are equally “back to nature,” built from timber and thatch with antique wood fans, driftwood framed mirrors, and balconies or terraces overlooking the sea and jungled estate—though it’s the property’s commitment to its community, employing only locals while investing millions into education programs, that keep the crowds coming, including perhaps its most famous regular, Mad Men star John Slattery.

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Exterior view of Jake's in Jamaica


This low-key hangout, on Jamaica’s quieter southern coast, is boho-chic at its best: 23 colorful cottages and bungalows that line the shore liven up the otherwise sleepy coastal town of Treasure Beach, but everything else is as mellow as it comes—informal and friendly staff, incredible sea views, greenery everywhere, a menu of yoga retreats, and Dougie’s Bar, where guests congregate for a glass (or three) of its legendary rum punch. Don’t miss lunch or dinner at Jack Sprat’s, where local and sustainable produce and seafood can be enjoyed alongside a weekly beach bonfire.

Bedroom at Round Hill Hotel and Villas
Exterior view of Round Hill Hotel and Villas
Living room at Round Hill Hotel and Villas

Round Hill Hotel and Villas

Few hotels have as much star power as Round Hill—the setting for Indina Menzel and Taye Diggs’ wedding, the film How Stella Got Her Groove Back, and vacations for visionaries like Alfred Hitchcock and Stevie Wonder. The draws: a polished Ralph Lauren design in a palette of white and mahogany, service on the private beach, an open-air spa, and themed dinners with live music (reggae; calypso) that keep the party going well past sunset.

Ocean view from The Cliff Hotel
Bedroom at The Cliff Hotel
Exterior view of The Cliff Hotel
Lobby at The Cliff Hotel

The Cliff Hotel

A multi-million dollar upgrade has given new life to the 33-room Cliff Hotel, and we’re loving the results: the lobby is now open and looks directly onto the central pool and ocean beyond, there’s a new yoga pavilion and fitness center for those wanting a tune-up before their beach-side lounge session, and upgraded suites (among Jamaica’s largest) now feature modern Caribbean design and hammocks on private verandahs that overlook the Caribbean Sea. After a soothing volcanic island stone massage at KiYara Spa, tuck into Jamaican-inflected cuisine at the newly expanded restaurant Zest, overseen by award-winning chef Cindy Hutson.

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The Caves
Exterior of The Caves
Ocean view from The Caves

The Caves

This isn’t your average all-inclusive: The Caves is comprised of just 12 thatched-roof wooden cottages and a villa scattered along a limestone cliff, where the drinks are strong and free-flowing, there’s table service for every rave-worthy meal—breakfast included—which features passed-down recipes prepared by native chefs, and rooms are as charming as they come (think vaulted ceilings, hand-painted furniture, local art, and louvered windows that frame the glittering Caribbean). Take a walk along the cliffs to find cutouts where the very adventurous jump into the sea, then head down to the shore and cross the footbridge to Blackwell Rum Bar, where some of the island’s best rum punches are served in a private grotto.

Private deck at Geejam
Pool at Geejam
Bedroom at Geejam


Like Strawberry Hill, Geejam was built based off the island’s formidable musical past, where its five cabins are named after Jamaican music genres and there’s a music studio onsite—though it’s the property’s sense of seclusion (on a rain-forested hilltop a few miles outside the tiny town of Port Antonio) that continues to draw the day’s biggest stars including John Legend, Rihanna, and Björk. The private beach is unparalleled, but days are often better spent holed up in your own incredibly spacious abode—which, depending on your choice, comes with its own hammock, recording studio, or stencils by Banksy, who let his own creative juices flow here.

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