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Iconic 110-Acre Peninsula Sanctuary • Est. 1953

Round Hill Hotel and Villas

Montego Bay, Jamaica • Ralph Lauren Design • Private Staffed Villas

A timeless 110-acre ocean peninsula overlooking the calm turquoise waters of Round Hill Bay. Experience 36 oceanfront guest rooms custom-designed by Ralph Lauren, 27 private hillside villas with private pools and dedicated staff, an 18th-century Great House Elemis spa, and celebrated seaside dining.

The Vincent Vacations Advantage

As an authorized Signature Travel Network agency, Vincent Vacations secures valuable VIP privileges on every reservation at Round Hill Hotel and Villas at no additional cost.

Daily Full Breakfast for Two

Complimentary full breakfast for two guests daily served at Seaside Terrace or prepared in your private villa ($80 daily value).

💎
$100 USD Resort or Spa Credit

USD $100 resort credit per room per stay, valid toward Elemis Great House Spa therapies, Seaside Terrace dining, or water excursions.

Priority Room Upgrade

Complimentary category upgrade to the next view, suite, or villa tier upon arrival, subject to hotel availability.

Early Check-In & Late Check-Out

Priority consideration for flexible early arrival and late departure, maximizing your time on Round Hill Bay.

Understated Elegance on a Private Jamaican Peninsula

Perched on a lush 110-acre peninsula overlooking the calm turquoise waters of Round Hill Bay, Round Hill Hotel and Villas represents the quintessential Golden Age Caribbean escape. Since welcoming its first guests in 1953 - including JFK and Jacqueline Kennedy (who honeymooned in Villa 10), Grace Kelly, and Ian Fleming - Round Hill has paired warm, attentive Jamaican hospitality with peerless style.

Accommodations include 36 Pineapple House oceanfront rooms custom-designed by Ralph Lauren with four-poster mahogany beds, crisp white palettes, and Waterworks deep soaking tubs. Tucked along the hillside, 27 private 2- to 6-bedroom villas offer open-air living verandas, private or semi-private swimming pools, and dedicated villa staff (cook, housekeeper, and gardener) who handcraft fresh breakfasts on your private terrace each morning. Spend afternoons relaxing by the Thomas Woltz double-edged infinity pool, indulging at the 18th-century Great House Elemis spa, playing tennis, or sailing along the private peninsula.

  • Private 110-Acre Ocean Peninsula Sanctuary
  • 36 Oceanfront Rooms Designed by Ralph Lauren
  • 27 Hillside Villas with Dedicated Staff & Pools
  • Thomas Woltz Double-Edged Infinity Pool
  • Oceanfront Elemis Spa in 18th-Century Great House
  • Farm-to-Table Dining at Seaside Terrace & The Grill
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Thomas Woltz double-edged infinity pool overlooking the Caribbean Sea

Ralph Lauren Rooms & Staffed Hillside Villas

From Ralph Lauren-styled oceanfront rooms steps from the beach to secluded multi-bedroom hillside villas with private pools and dedicated staff.

Pineapple House Oceanfront Room custom-designed by Ralph Lauren 460 Sq Ft • Ralph Lauren Design

Pineapple House Oceanfront Rooms

460 sq ft rooms custom-designed by Ralph Lauren featuring four-poster king mahogany bed, louvered windows framing Round Hill Bay, and Waterworks bathroom with soaking tub.

🛌 1 King or 2 Doubles 👥 2-3 Guests
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One-Bedroom Hillside Villa Suites Up to 1,400 Sq Ft • Semi-Private Pool

One-Bedroom Hillside Villa Suites

Spanning up to 1,400 sq ft of indoor-outdoor living, featuring open-air living veranda, lush garden setting, access to semi-private pool, and dedicated personal housekeeping service.

🛌 1 King Bed 👥 2-3 Guests
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Classic & Signature Hillside Villas with private pool 2-4 Bedrooms • Private Pool • Staffed

Classic & Signature Hillside Villas (2-4 BR)

Spacious 2,500 to 4,200 sq ft private estate villas featuring dedicated cook and housekeeper, private swimming pool, open-air living pavilions, and lush tropical flora overlooking the Caribbean Sea.

🛌 2 to 4 Bedrooms 👥 4-8 Guests
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Estate Luxury Villas (5 & 6 Bedrooms) Up to 5,700 Sq Ft • Multi-Pool Grand Estate

Estate Luxury Villas (5 & 6 Bedrooms)

The pinnacle of Caribbean luxury spanning up to 5,700 sq ft, offering multi-pool estates, Bose sound systems, game salons, mahogany libraries, and full private staff dedicated exclusively to your group.

🛌 5 to 6 Bedrooms 👥 10-14 Guests
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Farm-to-Table Oceanfront Dining

From fresh catch under the almond trees on Seaside Terrace to rooftop pimento wood grilling and personalized in-villa chef service.

The Seaside Terrace Restaurant

The Seaside Terrace

Contemporary Jamaican • Breakfast, Lunch & Dinner

Set directly over the water under the shade of ancient almond trees, serving fresh tropical breakfasts, midday salads, and evening catches of the day. Home of your complimentary daily Signature breakfast.

The Grill at Round Hill

The Grill at Round Hill

Pimento Wood Grill • Dinner

Perched above the terrace with gentle sea breezes, The Grill features Jamaica's only indoor pimento wood grill, serving prime grass-fed steaks, grilled lobster, and organic produce sourced from the resort's on-site garden.

The Beach Bar & Cocktail Lounge

Beach Bar & Cocktail Lounge

Ralph Lauren Styled • All Day & Evening

Designed by Ralph Lauren with monochromatic black-and-white photographs of famous guests, serving signature rum punches, handcrafted cocktails, and light beachside refreshments.

In-Villa Private Breakfast & Dining

In-Villa Chef Service

Custom Jamaican Comfort • Made-to-Order

Every villa guest enjoys bespoke breakfasts prepared fresh each morning by their dedicated cook, from Blue Mountain coffee and fresh-squeezed juices to authentic ackee and saltfish on your private veranda.

Frequently Asked Questions

Helpful information for planning your luxury getaway at Round Hill Hotel and Villas.

Through our Signature Travel Network partnership, Vincent Vacations guests receive complimentary daily full breakfast for two at Seaside Terrace or made-to-order in your villa ($80 daily value), a $100 USD resort or spa credit per room per stay (valid toward Elemis Great House Spa therapies, dining, or water sports), priority room category upgrades, and flexible early check-in and late check-out based on availability.
Pineapple House comprises 36 oceanfront guest rooms directly behind the beach and pool, all custom-styled by Ralph Lauren with four-poster mahogany beds and ocean views. The 27 hillside villas are multi-bedroom private compounds with open-air living pavilions, private or semi-private pools, and dedicated personal staff including a private cook, housekeeper, and gardener.
Opened in 1953 by Jamaican entrepreneur John Pringle, Round Hill quickly became the private retreat of international high society. John F. Kennedy and Jacqueline Kennedy spent their honeymoon in Villa 10, where JFK also drafted his famous Inaugural Address. Other notable guests include Grace Kelly, Ian Fleming, Noël Coward, and Ralph Lauren, who maintains two private villas on property.
The Spa at Round Hill is housed in a beautifully restored 18th-century plantation Great House set on an oceanfront bluff. Treatments utilize award-winning Elemis botanical products and locally sourced Jamaican healing herbs, complemented by open-air oceanfront treatment gazebos, an outdoor hydrotherapy pool, and seaside yoga pavilions.
Round Hill is located approximately 25 minutes west of Sangster International Airport (MBJ) in Montego Bay. Vincent Vacations advisors can arrange private chauffeured VIP luxury transfers directly from the airport terminal to the resort gates.

Plan Your Round Hill Getaway

Contact our dedicated Jamaica luxury travel specialists to confirm dates, unlock Signature VIP amenities, and tailor custom island itineraries.

  • Complimentary Daily Full Breakfast for Two ($80 Value)
  • $100 USD Resort or Spa Hotel Credit per Room
  • Priority Room Category Upgrade & Flexible Check-in/out
  • Dedicated Private Staff for Hillside Villas

Request VIP Quote

Complete the form below and an advisor will respond within 24 hours.