From $2,354 USD - $6,726 USD / nt
Plan Your Trip
HAVE QUESTIONS?
USA/CANADA: +1 347 707 1195
BARBADOS: +246-432-6307
UK / INTERNATIONAL: +44 1978 368531
From $2,354 USD - $6,726 USD / nt
We love this villa because...
We love this villa because Little Hill combines timeless West Indies elegance with modern luxury, offering stunning Caribbean views, a private pool, tennis court, and fully staffed service for an unforgettable stay.
Little Hill – Elegant Villa at Tryall Club, Jamaica
Set high on a five-acre hilltop within the exclusive Tryall Club estate, Little Hill is a timeless masterpiece among luxury villas in Jamaica. Designed by renowned architect Robert Hartley, the villa captures the essence of classic West Indies style, offering sweeping 360-degree views of the Caribbean Sea, tropical hillsides, and Tryall’s championship golf course.
Villa Highlights
5 spacious en-suite bedrooms – accommodates up to 10 guests.
Private circular swimming pool set in a charming courtyard.
Exclusive on-site tennis court – unique within the Tryall Club.
Expansive terraces for dining and entertaining with seating for 24.
Tropical gardens filled with fruit trees and vibrant flowers.
Elevated position ensures refreshing ocean breezes year-round.
Timeless Caribbean Elegance
Built around a striking 30-foot-diameter pool, Little Hill blends open-air living with elegant interiors. Solid mahogany floors, cathedral ceilings, and finely chosen furnishings create a refined yet welcoming atmosphere. The grand entrance foyer with cut-stone flooring sets the tone for a villa designed for both relaxation and entertaining.
Luxurious Bedrooms
Each of the five bedrooms is designed with comfort in mind:
En-suite bathrooms and generous closet space.
Air conditioning, ceiling fans, and flat-screen TVs.
Wheelchair-accessible primary suite with adapted bathroom.
Wi-Fi connectivity throughout the property.
Dedicated Villa Staff
Guests at Little Hill are cared for by a professional household team, including:
Private chef preparing fresh Caribbean and international cuisine.
Butler and housekeeper.
Laundress.
Two gardeners maintaining the grounds.
This personalised service makes the villa ideal for family villa rentals in Jamaica, group celebrations, or a luxury Caribbean escape.
Access to Tryall Club Amenities
Staying at Little Hill means enjoying all the benefits of the prestigious Tryall Club:
Championship 18-hole golf course.
Private beach club and water sports.
Tennis courts and wellness facilities.
Fine dining and social activities.
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
Looking for Jamaica Villas to Rent?
Looking for Jamaica Villas to Rent?Caribbean Dream Villas, a trusted Caribbean villa specialist and part of Worldwide Dream Villas, offers a handpicked selection of luxury villas to rent in Jamaica. Whether you’re seeking a beachfront villa, a private pool retreat, or a family-friendly holiday home near Jamaica’s top attractions, we provide some of the finest Jamaica villa rentals available. Explore villas to rent in popular areas like Montego Bay, Negril, and Ocho Rios. With stunning ocean views, professional concierge services, and easy access to Jamaica’s best beaches, dining, and golf courses, our villas for rent in Jamaica are ideal for couples, families, and groups looking for a memorable Caribbean vacation. Book your perfect Jamaica villa getaway with Caribbean Dream Villas today!
Amenities
- Air Conditioned bedrooms
- Beach Club Facility
- Car Parking on site
- Children Welcome
- Childrens Activities
- Communal Facilities
- Golf Cart
- Golf Resort
- Gym/Fitness Room
- Near Beach
- Private Garden
- Private Pool
- Restaurant
- Safe
- Shop
- Sound System
- Spa
- Staffed Villa
- Sunbeds
- Tennis Court
- TV
- WaterSports
- Well Equipped Kitchen
- Wireless Internet
For Your Convenience:
Two golf carts included.
Bedroom : 5
Bathroom : 5
Staff
- Butler
- Chef
- Gardener
- House keeper
- Laundress
Rate
| 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.
Policy
Check In:
04 PM
Check Out:
11 AM
Location
Sangster Airport, Montego Bay - 30 minute drive
