
Sugar Magnolia
4 Bedrooms
From $1,714 USD - $3,450 USD / nt
From $2,354 USD - $6,726 USD / nt
Perched on a five-acre hilltop within the prestigious Tryall Club, Little Hill is one of the most elegant Jamaica villa rentals. This exquisite luxury villa in Jamaica combines timeless West Indies architecture with modern comforts, offering sweeping Caribbean Sea views, lush tropical gardens, and the rare privilege of a private tennis court.
5 en-suite bedrooms – sleeps up to 10 guests.
Private circular swimming pool at the heart of a charming veranda courtyard.
Exclusive private tennis court – the only villa at Tryall with this feature.
360-degree views of the ocean, tropical forests, and Tryall’s world-class golf course.
Fully staffed villa in Jamaica with chef, butler, housekeeper, laundress, and gardeners.
Two complimentary golf carts for exploring the Tryall estate.
Designed in 1959 by renowned architect Robert Hartley, Little Hill is a masterpiece of West Indies-style architecture. The villa is built around a striking 30-foot-diameter pool with expansive covered terraces, inviting guests to relax in shaded comfort while enjoying cooling ocean breezes at 200 feet above sea level.
Grand entrance with a two-level foyer and 18th-century cut stone floors.
Cathedral-ceiling living room, stylish bar, and card room.
100-foot-long terrace with seating for up to 24 guests.
Solid mahogany doors and floors throughout.
Thoughtfully curated interiors with fine linens, china, and furnishings.
Each of the five bedrooms offers privacy and comfort:
En-suite bathrooms and ample closet space.
Wheelchair-accessible primary suite and bathroom.
Air conditioning, ceiling fans, and flat-screen TVs in every room.
Wi-Fi available throughout the villa.
Guests at Little Hill enjoy the dedicated service of six household staff, including:
Private chef.
Butler.
Housekeeper.
Laundress.
Two gardeners.
This level of service makes Little Hill ideal for family villa rentals in Jamaica, special occasions, or group retreats.
As part of the Tryall Club, one of Jamaica’s most prestigious resorts, guests of Little Hill enjoy access to:
Championship golf course.
Private beach club.
Water sports.
Tennis courts.
Fine dining and wellness facilities.
If you are interested in renting this villa in Jamacia contact us today
Explore More Villas in Jamaica
USA/ Canada: +1 347 707 1195
UK / International : +44 1978 368531
Email: [email protected]
For luxury villas to rent in other areas of the Caribbean visit: www.worldwidedreamvillas.com
From | To | Min Stay | Nightly Rate | Weekly Rate |
---|---|---|---|---|
04-Jan-2026 | 06-Mar-2026 | 7 | $3,531 USD | $24,717 USD |
07-Mar-2026 | 27-Mar-2026 | 7 | $3,993 USD | $27,951 USD |
28-Mar-2026 | 24-Apr-2026 | 7 | $3,531 USD | $24,717 USD |
25-Apr-2026 | 24-Jul-2026 | 7 | $2,486 USD | $17,407 USD |
25-Jul-2026 | 30-Oct-2026 | 7 | $2,354 USD | $16,480 USD |
31-Oct-2026 | 20-Nov-2026 | 7 | $2,486 USD | $17,407 USD |
21-Nov-2026 | 28-Nov-2026 | 7 | $3,993 USD | $27,951 USD |
28-Nov-2026 | 11-Dec-2026 | 7 | $2,486 USD | $17,407 USD |
12-Dec-2026 | 18-Dec-2026 | 7 | $3,531 USD | $24,717 USD |
19-Dec-2026 | 02-Jan-2027 | 7 | $5,174 USD | $36,221 USD |
From | To | Min Stay | Nightly Rate | Weekly Rate |
---|---|---|---|---|
04-Jan-2026 | 06-Mar-2026 | 7 | $4,590 USD | $32,132 USD |
07-Mar-2026 | 27-Mar-2026 | 7 | $5,190 USD | $36,336 USD |
28-Mar-2026 | 24-Apr-2026 | 7 | $4,590 USD | $32,132 USD |
25-Apr-2026 | 24-Jul-2026 | 7 | $3,232 USD | $22,629 USD |
25-Jul-2026 | 30-Oct-2026 | 7 | $3,060 USD | $21,424 USD |
31-Oct-2026 | 20-Nov-2026 | 7 | $3,232 USD | $22,629 USD |
21-Nov-2026 | 28-Nov-2026 | 7 | $5,190 USD | $36,336 USD |
28-Nov-2026 | 11-Dec-2026 | 7 | $3,232 USD | $22,629 USD |
12-Dec-2026 | 18-Dec-2026 | 7 | $4,590 USD | $32,132 USD |
19-Dec-2026 | 02-Jan-2027 | 7 | $6,726 USD | $47,087 USD |
Rental rates are subject to 10.00 % TAX plus 7.50 % service charge.
Sangster Airport, Montego Bay - 30 minute drive
USA/CANADA: +1 347 707 1195
UK /International : +44 1978 368531
Barbados: +1 246-432-6307
Email : [email protected]
UK: 40 Knutsford Road, Alderley Edge, Cheshire SK9 7SF
Barbados: Indigo Courtyard, Holetown, Barbados Bb24917
A great way to communicate as we can answer your questions in real time. We are usually available 6 days a week between 9am and 8pm.