Little Hill
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Little Hill

Montego Bay , Tryall  Jamaica
5
5
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Little Hill
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Little Hill
From $2,354 USD - $6,726 USD / nt

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 – Luxury Villa at Tryall Club, Jamaica

Nestled on a five-acre hilltop inside the prestigious Tryall Club, Little Hill is a true jewel among luxury villas in Jamaica. Combining the elegance of classic West Indian architecture with modern comfort, this private retreat offers sweeping views of the Caribbean Sea, lush forests, and the renowned Tryall golf course.

Why Stay at Little Hill?

  • 5 en-suite bedrooms – ideal for up to 10 guests.

  • Private circular swimming pool framed by a charming courtyard veranda.

  • Exclusive tennis court – the only villa at Tryall with this feature.

  • Elevated position – spectacular 360-degree views and cooling sea breezes.

  • Expansive terraces – perfect for entertaining, with seating for up to 24 guests.

  • Impeccably landscaped gardens with tropical flowers and fruit trees.

Classic Caribbean Charm

Originally designed in 1959 by architect Robert Hartley, Little Hill embodies timeless Jamaica villa style. From its cathedral-ceiling living room and elegant bar to solid mahogany floors and carefully chosen furnishings, every detail reflects sophistication. The villa’s 100-foot terrace invites alfresco dining and social gatherings in true Caribbean fashion.

Elegant Bedrooms

All five bedrooms are designed for relaxation and privacy:

  • En-suite bathrooms and spacious closets.

  • Air conditioning, ceiling fans, and flat-screen TVs.

  • Wi-Fi throughout the villa.

  • Primary suite with wheelchair-accessible facilities.

Fully Staffed Villa in Jamaica

Guests are looked after by a warm, professional team, including:

  • Private chef creating tailored menus.

  • Butler and housekeeper.

  • Laundress.

  • Two gardeners.

This makes Little Hill perfect for families, groups of friends, or guests seeking a fully serviced private villa rental in Jamaica.

Tryall Club Lifestyle

Booking Little Hill includes access to all Tryall Club amenities:

  • Championship golf course.

  • Private beach club with water sports.

  • Tennis courts and wellness centre.

  • Fine dining and social events.

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

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
See more details...
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

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Get In Touch

CONTACT US

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

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