Top-shelf resorts and villas in Jamaica: Swanky stays for a luxury getaway

Photo courtesy of Round Hill Hotel and Villas

Easy like Sunday morning in Villa 20 at Round Hill Hotel and Villas

Laying claim to some of the best resorts, spas and restaurants in the Caribbean, Jamaica is a leader in luxury and it's where you’ll find the swankiest of the swanky in penthouse suites, charming cottages and villas that steal the show.

West of Montego Bay, Round Hill Hotel and Villas comes with a fabled past and guestbook that includes JFK and Jackie Kennedy,  Prince Harry, Beyoncé and Ralph Lauren who designed 36 oceanfront guestrooms.

Taking swanky to the next level, Villa 20, one of 27 villas at the classy resort – and the largest of three Premium Luxury Villas – invites with two pools, six bedrooms, eight bathrooms and a pillow menu from "Snore to Feather." 

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Photo courtesy of Round Hill Hotel and Villas.

A pair of perfect pools grace Villa 20 at Round Hill Hotel and Villas

Relaxing poolside is the stuff of vacation magic in the 6-bedroom Villa 20 at Round Hill Hotel and Villas, west of Montego Bay. Keeping the theme for water aficionados, head to the beach where snorkeling, pedal boats, kayaks and glass-bottom boat rides are included in villa stays. Also included is afternoon tea, served daily at 4 pm in the Cocktail Bar, and play on five tennis courts – two of them lit for a nighttime match.

Nightly rates start at $5,799.

Photo courtesy of Your Jamaican Villas

Live the fantasy at Rio Chico

Reminiscent of a Monet painting with lily ponds, manicured lawns and ivy-covered stone bridges, Rio Chico, just outside Ocho Rios, is an exquisite Private Estate Villa with a six-bedroom Manor House, four-bedroom Cliff-side Villa and two-bedroom Cottage.  

Super luxe perks include sea toys like sailboats and kayaks, two private beaches, tennis, chef, butlers, oversized Jacuzzi, 24-hour security and four pools including the spectacularly secluded Hidden Sanctuary Pool tucked into the cliffs just steps from the Caribbean Sea. Weekly rates start at $59,485.

Hotels & Resorts: Escape to the Caribbean with a splurge at one of these luxury stays

Photo courtesy of Eric Stein Photography

At Eclipse at Half Moon, grand outdoor living spaces and views of the Caribbean Sea

Ten minutes from Sangster International Airport in Montego Bay, four-bedroom Estate Ocean Suite at Eclipse at Half Moon features a roomy dining area with seating for up to eight people. A celebration of Jamaican culture, Eclipse at Half Moon, flanked by the green hills of Montego Bay and the Caribbean Sea, is luxury living with two restaurants, three bars, market café, Fern Tree Spa, infinity edge pool and private beach with a natural swimming cove.

Nightly summer rates in the Estate Ocean Suite designed with outdoor showers, wraparound balconies, patios and sea views start at $4,200.

Photo courtesy of Villas of Distinction

Happy place in the Happy Hour Villa on the north coast

On the shores of Discovery Bay, the aptly named Happy Hour Villa is Instagram gold in 13,000 square feet of pure pleasure. Beachfront with seven bedrooms, perks include butlers, chefs including a pastry chef, private beach and an infinity edge pool with a shallow area for kids.

Big on the wow factor, the modern design includes a bar with an 86-inch TV, tennis court, hot tub that fits 10 and  massage room. Add kayaks, paddle boards and a pool table, and you’ll remember why you booked a vacation in the first place. Spacious enough to sleep 12 adults and 6 children, nightly rates through November 19th start at $3,715, with a 5-night minimum stay. 

Photo courtesy of The Tryall Club

Villa Amana is a 10-bedroom stunner at The Tryall Club in Montego Bay

A two-level villa with 10 bedrooms, Villa Amana at The Tryall Club in Montego Bay is striking with white walls, ocean views at the front and the hillside forest as a verdant backdrop. With a staff of six, the tony villa is outfitted with an infinity edge pool with a poolside bar that salutes the sea, children’s playground, basketball court and gym.

For the golfers in the house, the 18-hole, 6,836-yard course at The Tryall Club is one of the finest on the island. 

Photo courtesy of The Tryall Club

To-dine-for at Villa Amana at The Tryall Club in Montego Bay

One of the largest villas at The Tryall Club in Montego Bay, entertaining at Villa Amana is a breeze in the formal dining room with a stately mahogany table flanked by pineapple-back chairs. Big enough for a multi-generational stay, this villa with a dedicated staff of six hosts an expansive main balcony ideal for a cocktail party at sunset. 

Weekly rates start at $23,740 through December 18.

The Tryall Club Classically Jamaican-Exclusively Private-Naturally Beautiful. To the west of Montego Bay in the Jamaican parish of Hanover awaits an experience that is both exhilarating and a way of life. Since 1959 The Tryall Club has...  Read More

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Photo courtesy of Hyatt Ziva Rose Hall

A regal stay in the Presidential Suite at the Hyatt Ziva Rose Hall in Montego Bay

Measuring 2,500 square feet, the Presidential Suite at the Hyatt Ziva Rose Hall is one of a kind at the all-inclusive seaside resort in Montego Bay. Designed with space in mind, the sweet suite comes with walk-in closets in the bedroom, rainfall shower in the big bathroom, expansive living and dining areas and butler service from 7 am to 10 pm.

Suite stayers enjoy unlimited sips and snacks at a variety of restaurants, bars and lounges, snorkeling in the Caribbean Sea, catching a wave on a boogie board, and nightly entertainment, such as Jamaican street music and steel drum performances. Nightly rates, double occupancy, start at $1300.

Hyatt Ziva Rose Hall Hyatt Ziva Rose Hall puts you within a 15-minute drive of Doctor's Cave Beach and features a free airport shuttle. You can visit the fitness center for a workout or unwind with a drink at the bar/lounge. There's also an...  Read More

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Photo courtesy of Villas of Distinction

Chefs, cocktails and a hot tub for 10 at Canoe Cove on the Beach

Ninety minutes from the Sangster International Airport, Canoe Cove on the Beach is a spacious seven-bedroom villa, just three minutes from the iconic Dunn’s River Falls. West of Ocho Rios, the beachfront villa is fully staffed with two chefs and impeccably outfitted with a Junior Olympic-size swimming pool with 3 competition lanes, kayaks, green clay tennis court, five-hole putting green and a private massage room for recharging after a sporty day.

For real rejuvenation, the hot tub fits 10 and the thatch roof gazebo and bar is picture-perfect for open-air dining and  cocktails at sunset. With a nod to the whimsical, a pendant lamp in the hallway is crafted of old magazines, and real telephone poles with bamboo-clad bases support the gazebo.

Nightly rates through November 19 start at $3,524, with a 5-night minimum stay required.

Photo courtesy of Nigel Lord

Blue on blue at the Sea Biscuit Villa at Hermosa Cove

An all-villa hotel near Ocho Rios, Hermosa Cove is all about a laid-back artsy vibe on the island’s north coast. Originally built in the 1950s, Sea Biscuit Villa welcomed Hollywood A-listers like Marilyn Monroe and Joan Collins, and it was the location backdrop for the 1957 film "Sea Wife" starring Richard Burton.

Reimagined and restored to its original glory, this three-bedroom oceanfront villa features a private dip pool, airy dining area and 5,000 square feet of outdoor living space. With its twin stone piers, Christopher’s Beach, just steps from the villa, is the launching pad for kayaking and snorkeling.

Capping the piers, the gazebos are glorious for a mellow massage, private dining and a front-row seat for spectacular sunset viewing. Weekly rates start at $8,820 with a 5-night minimum stay.  

Photo courtesy of Sandals Resorts

Slow your roll in Villa Plantana at Sandals Royal Plantation

Privacy is the new luxury at Villa Plantana at the adults-only Sandals Royal Plantation in Ocho Rios. Perched above the resort's quiet East Beach, the butler-staffed villa with a private pool is postcard-perfect with sweeping vistas of the Caribbean Sea. Three bedrooms are outfitted with four-poster beds, and patios are cooled by the sea breeze.

Dining options go the distance, from room service and apps and cocktails prepared by the villa staff to chowing down at six restaurants at the all-inclusive resort. Enjoy tee time at the nearby Sandals Golf & Country Club where golf privileges are included in villa stays. Nightly rates, per person, start at $975.

Sandals Royal Plantation - ALL INCLUSIVE Couples Only With a stay at Sandals Royal Plantation - ALL INCLUSIVE Couples Only in Ocho Rios, you'll be next to a golf course, just steps from Coconut Grove Shopping Village and a 2-minute drive from White River Reggae Park. Featured...  Read More

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Photo courtesy of Jeremy Francis

The star attraction at the Seaweed Villa at Jakes are the never-ending sea views from the pool deck

Boho chic on the less-traveled south coast, Jakes on Treasure Beach is an island classic. On 1.5 acres, the crème de la crème is the Seaweed Villa with four bedrooms, patios and outdoor showers in the main villa, and three bedrooms and a plunge pool in the smaller cottage. 

Both can rent together or just one for a more intimate stay. An infinity pool with a hot tub are relaxation-central, while the private beach cove is where you’ll find kayaks, snorkeling gear and boogie boards. Villa perks include a chef, concierge, barbecue grill, outdoor bar, dining area and bicycles ideal for exploring the resort.

Nightly rates start at $990 and include mesmerizing vistas of the Caribbean Sea from the pool deck. 

Photo courtesy of Jamaica Inn

At Jamaica Inn, Cottage 7 is the largest luxe retreat at the storied Inn on the north coast

The epitome of elegance for more than six decades, Jamaica Inn in Ocho Rios is where Marilyn Monroe and Arthur Miller toasted their honeymoon, spy novelist Ian Fleming sipped martinis and Katharine Hepburn relaxed in the lounge. Oozing privacy around every palm tree, Cottage 7 is the largest of the tastefully-appointed cottages clocking in at 2,200 square feet.

Inviting with ocean views, access to a private cove and an infinity plunge pool, complimentary Planters Punch is served on the beach from 11 am to noon. Nightly rates start at $1,233 and include non-motorized water sports, from kayaking and sunfish sailing to paddle boarding and snorkeling.