Key Highlights
- The breathtaking ten mile ocean views stretching all the way to Montego Bay, best enjoyed from the expansive furnished verandah as the city lights shimmer across the water at night
- The seamless blend of Old Jamaica charm and modern comfort, with coral stone floors, airy interiors and cooling trade winds flowing throughout the villa
- Large 20 x 40 foot private pool with panoramic sea views, perfectly positioned for long, sun drenched days and relaxed evenings by the fire pitlarge 20 x 40 foot private pool with panoramic sea views, perfectly positioned for long, sun drenched days and relaxed evenings by the fire pit
- Exclusive access to both Round Hill and the prestigious Tryall Club, unlocking beaches, pools, tennis, gym facilities, kids clubs and a vibrant calendar of resort experiences
The Villa
Interior- 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
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.
- Bedrooms are air conditioned, while the main living areas are naturally cooled by ceiling fans and refreshing trade winds
- Access to certain facilities, dining venues, spa treatments, golf and select resort events at Round Hill and Tryall Club may incur additional fees
- The villa is fully staffed with a cook, butler, housekeeper, laundress and gardener to ensure a relaxed stay
- Kids should be supervised around the pool area at all times
Oliver's Extras
- Chef/Cook Included
- Maid Service Included
- Butler Included
- Round Hill Membership
- Tryall Club Membership
At Oliver’s Travels we pride ourselves on going that little bit further for our guests. From private chefs to travel services we can help you arrange those little extras that make it a truly memorable holiday. Simply fill in the concierge request form or contact the Oliver’s Concierge Team who will be happy to help. We can typically help you arrange any of the following:
- Maid service/extra cleaning
- Private chef/cook/catering
- Welcome hamper/pre-stocked fridge
- Local day-trips or tours
- Airport transfers
Simply fill in the concierge request form or contact the Oliver’s Concierge Team.
Please note that all extras are subject to availability and must be requested in advance of the holiday (prices on request). Due to some rural/remote locations, not all services will be available at all properties. However, we will always do our best to fulfil your requests!
