About this property
Perched high above the storied Round Hill Estate, Villa Hillside is embraced by sweeping ten mile views of sea and sky, where cooling trade winds drift gently through coral stone interiors. The timeless spirit of Old Jamaica is beautifully preserved, while every modern comfort has been thoughtfully integrated to create a relaxed yet refined retreat. The Great Room opens onto a broad furnished verandah, revealing a breathtaking panorama that stretches to Montego Bay, where distant city lights shimmer across the water each evening. Candlelit dinners and sunset cocktails are best savoured here, with the balmy air and uninterrupted views forming an unforgettable backdrop. A large private 20 x 40 foot pool rests along the terrace, accompanied by a fire pit and outdoor shower, inviting long afternoons beneath the Caribbean sun. Privately tucked into the east side of the hill, the villa feels secluded and serene, yet remains only minutes from Round Hill’s celebrated amenities and less than half an hour from the international airport.
Five beautifully appointed bedrooms are arranged with families in mind, including two expansive master suites on the pool terrace level that open directly to the lawn and sea views. Upstairs, additional bedrooms feature furnished balconies or garden access, with optional connecting suites ideal for parents and children. Each bedroom offers quiet air conditioning, ceiling fans, smart televisions, safes and elegant en suite bathrooms. A dedicated team comprising a cook, butler, housekeeper, laundress and gardener ensures every detail is effortlessly managed, while a complimentary six seater cart provides easy access throughout Round Hill. Guests enjoy membership at both Round Hill and the prestigious Tryall Club, with access to beaches, pools, tennis, gym facilities, children’s clubs and a host of resort experiences designed for every generation.
On a sun-drenched peninsula just west of Montego Bay, Round Hill Estate is Jamaica at its most refined and radiant. Fringed by white sand coves and crystalline Caribbean waters, this storied enclave blends timeless glamour with effortless island living. Days unfold at an unhurried pace as you snorkel along coral reefs alive with tropical fish, paddleboard across glassy seas at sunrise, or tee off on championship golf courses with sweeping ocean views. Beyond the gates, discover the rhythm of Montego Bay’s Hip Strip, explore the cascading Dunn’s River Falls, raft along the Martha Brae River, or tour historic great houses that whisper tales of the island’s past. Evenings invite rum tastings, beachfront dining beneath swaying palms, and sunsets that set the horizon ablaze in gold and rose. At Round Hill, every moment feels curated yet carefree, an elegant retreat where Jamaica’s natural beauty, culture and warm hospitality shine in perfect harmony.
Accommodation
The VillaInterior- Spacious Great Room with comfortable seating, television and direct access to a broad furnished balcony verandah with panoramic ten mile ocean views
- Formal and al fresco dining areas
- Five bedrooms, all with en suite bathrooms, walk in showers, safes, flat screen Smart televisions, ceiling fans and quiet remote control air conditioning
- Two master suites on the pool terrace level with king size beds, en suite bathrooms with bathtubs and walk in showers, and direct access to the lawn and pool terrace
- Bedroom with queen size bed, en suite bathroom and access to a furnished verandah with sea views
- Bedroom with optional king or twin beds, en suite bathroom with octagonal walk in shower and access to verandah, with optional connection to adjoining bedroom
- Bedroom with optional king or twin beds, en suite bathroom and access to a private tropical garden courtyard, with optional connection to neighbouring bedroom
- Coral stone floors throughout
Exterior Grounds
- Private ocean view swimming pool (20 x 40 feet)
- Expansive pool terrace with panoramic sea views
- Furnished balcony verandah overlooking Montego Bay
- Lawn area
- Fire pit
- Outdoor shower
- Private tropical garden courtyard
Additional Facilities
- Complimentary Wi Fi throughout the villa and Round Hill
- Fully staffed with cook, butler, housekeeper, laundress and gardener
- Hair dryers in bathrooms
- iPod docks
- Room safes in every bedroom
- Round Hill membership
- Tryall Club membership
- Complimentary six seater transportation cart for use within Round Hill Estate