Jamaica

Round Hill Hotel & Villas has held its private hundred-acre peninsula in Montego Bay, Jamaica since 1953, still among the island's most discreet legends. Once a pineapple plantation, the gated estate sits about 25 minutes from Sangster International Airport, with helicopter arrivals from Kingston. A golden-sand beach traces the shoreline, an infinity pool hangs between green hillside and blue water, and the trade winds find their way into every room. The seafront Pineapple House holds 36 ocean-view rooms, each designed by Ralph Lauren in his signature white-on-white: four-poster beds, pale stone floors, and crisp linens, more composed than showy, with the Caribbean framed in the doorway. Across the peninsula stand 27 private villas, from two to six bedrooms, most with their own pool and a dedicated butler, chef, and gardener; suites with private pools offer the same seclusion, scaled down. Each villa is privately owned and let only when its owner is away, so all carry their own character, full of antiques and the quiet patina of the plantation years.

Dining is led by award-winning executive chef Martin Maginley, whose Light Clean Caribbean Cuisine treats Jamaican produce with a bright, unfussy hand. The seafront Seaside Terrace anchors the day, where the waves and a cup of Jamaican Blue Mountain coffee make a memorable morning, before the bars take over after dark. The spa occupies a restored 18th-century great house above the sea, with outdoor aromatherapy massages and an open-air pavilion for meditation and breathwork. Active days fill with tennis and pickleball, snorkeling, or the peninsula trail and its views over the bay, while families lean on the Pineapple Club, the 7-Up Club, and attentive nanny service.

Expect a red carpet welcome (and white glove service) from the moment you arrive at Bluefields Bay. With a butler – not to mention nannies, private chef and personal concierge – you’ll have your very own pristine corner of paradise. And as each expansive villa faces the aquamarine sea on the waterfront, you’re also guaranteed the best views in the house.

Whether it’s two bedroom Cottonwood Cottage or San Michele (with space for 13, footbridge to a private island and helicopter pad), each Bluefields Bay residence takes luxury to new levels. From each you can sail, kayak or snorkel in the ocean. Dip into the just for you pool. And enjoy tailor made menus cooked for all the family on your private pavilion. The beach is only ever footsteps away, perfect for a couple’s massage on the sand, as the sound of the waves washes over you.

Sitting alongside the famous Doctor’s Cave Beach, S Hotel Jamaica All-Inclusive Boutique Hotel boasts some of the finest coastal views Jamaica has to offer. It’s close enough to Montego Bay’s Hip Strip for party all nightlife, but far enough away to enjoy the tranquillity of the hotel’s private beach. Grand windows frame quintessential Caribbean scenes: swaying palms and the open sea. And top floor lounges and decks let you bask in the lively tropical atmosphere.

Inside, the rooms at S Hotel are designed to refresh and relax. Crisp white, dark oak and wicker are the perfect match for the breath-taking ocean views. Plus there’s plenty of space to stretch out and make yourself at home. Over at the pool, enticing smells of locally inspired food (from curries to cakes) fill the bar and grill – a reminder of the culinary treats Montego Bay is renowned for. That’s not forgetting the urban elegance of the Rocksteady restaurant, where your food is served beneath colourful prints by renowned Jamaican artist Michael Thompson.

A peaceful beach lapped by warm, aquamarine waters. A jungle backdrop, where crystalline lagoons and waterfalls wait hidden beneath the canopy. And in between the two sits The Trident hotel, its 13 private villas adding splashes of pure white to the colourful Caribbean canvas. Away from sun seeking crowds, this exclusive Port Antonio retreat must be one of Jamaica’s best kept secrets.

Your villa gives you plenty of space to play with from the mid century modern interior to the private deck and plunge pool. There’s lots to enjoy outside your personal paradise, too. Claim a lounger beside the oceanfront infinity pool, or wander down to the private beach. Stretch out on the sand, or go kayaking or snorkelling with the water sports guide. If you have total relaxation in mind, pay a visit to The Trident Spa – or have a therapist come to your villa. As evening falls, the pace picks up, with dinner followed by live jazz at speakeasy style Mike’s Supper Club.