Hammerstein Highland House

Hammerstein Highland House (US$7,500/9,500 weekly, low/high season, four-night minimum) is a six-bedroom villa on a lush 17-acre estate overlooking Montego Bay in the community of Content that once belonged to American musical theater director Oscar Hammerstein II, who wrote the score to The Sound of Music while at the property. Hammerstein bought the retreat from its original owner, English actress Gladys Cooper, who built the villa in the 1940s. With its open design and countless areas for socializing and relaxing, it's easy to imagine the kind of parties hosted at HHH by its former owners. Smaller groups can opt to as few as four bedrooms at a reduced rate (US$6,500/8,500 weekly, low/high season). Two rooms have king-size beds. Another room has a queen-size bed and the best view of Montego Bay in the house. Three rooms have two twin beds each, which can be converted to king-size beds when preferred. Amenities include WiFi throughout, a 35-foot pool and beach club membership at Round Hill. All rooms have antique furnishings, AC and satellite TV. The elevation, cool breeze and louvered, screened windows contribute to perfect temperatures inside and out without needing to turn on the AC. The lounge has a fireplace and plush couches, flat-panel TV and conga drums. There's no shortage of relaxing nooks and dining areas around the pool and on the balcony overlooking the sloping lawn, broad cotton tree, organic farm and harbor. There's also a billiards table, dart board and bar on the lower level. A short walk down a wooded staircase leads to a screened-in yoga pavilion with ceiling fans that accommodates up to 12 adults, making the property a favorite for yoga retreats. A housekeeper, butler, cook, laundress, gardener and farmers are attentive and take care of every need. The two-acre organic farm on property supplies fresh produce to villa guests for delicious farm-to-table salads and also provides produce to Round Hill Hotel and supports schools in the surrounding community as part of the owner's One Love Learning Foundation (www.onelovelearningfoundation.org) with its focus on "Soil, Soul and Society". It's a worthy non-profit that supports schools in Atlanta, the current owner Brenda Isaac's hometown, Jamaica and South Africa.