Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook

Overlook

Montego Bay , Tryall  Jamaica
5
5
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Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
Overlook
From $1,846 USD - $5,082 USD / nt

From $1,846 USD - $5,082 USD / nt

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USA/CANADA: +1 347 707 1195
BARBADOS: +246-432-6307
UK / INTERNATIONAL: +44 1978 368531
From $1,846 USD - $5,082 USD / nt
We love this villa because...
We love this villa because it offers the perfect mix of luxury and privacy, with breathtaking Caribbean Sea views, a heated infinity pool, and a dedicated staff that makes every stay effortless.

Overlook Villa – Jamaica Luxury Villa at Tryall Club

Elevated Living with Endless Caribbean Views

Set high in the hills of the prestigious Tryall Club, Overlook Villa offers one of the most impressive vantage points in Jamaica. With sweeping views of the Caribbean Sea, lush gardens, and tropical blooms, this villa delivers the perfect balance of privacy, comfort, and island elegance. Guests can enjoy the club’s private beach, championship golf course, tennis courts, spa, and dining venues—all just minutes away by golf cart or on foot.

Key Features

  • 5 spacious bedrooms, ideal for up to 10 guests.

  • Bright and breezy interiors with classic Caribbean décor.

  • Expansive heated infinity pool with jacuzzi platforms and fountain feature.

  • Tranquil hillside setting surrounded by royal palms and bougainvillaea.

  • Convenient access to Tryall Club’s world-class amenities.

Villa Staff & Service

Staying at Overlook means enjoying the ease of a fully staffed Jamaica private villa rental. Your dedicated team includes:

  • Butler to arrange daily activities and island excursions.

  • Private chef to prepare personalized menus.

  • Housekeeper and laundress for effortless living.

  • Gardener to maintain the tropical grounds.

Comforts & Amenities

  • Indoor dining room with air conditioning and open-air dining options.

  • High-speed Wi-Fi, surround sound, and SMART TVs with international channels.

  • Relaxed island atmosphere paired with modern comforts.

Why Choose Overlook Villa?

This villa is the perfect choice for guests seeking luxury Jamaica villas to rent with space, privacy, and first-class service. Whether you’re planning a family villa holiday in Jamaica, a group getaway, or a Caribbean retreat with friends, Overlook offers the ideal blend of seclusion and access to the best of the island.

Perfect For

  • Families or groups searching for holiday villas to rent in Jamaica.

  • Travelers looking for luxury Caribbean villas with staff.

  • Guests wanting a villa with private pool and stunning sea views.

  • Anyone seeking an exclusive Jamaica villa rental within a private club.

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
  • Air Conditioning
  • Beach Club Facility
  • Ceiling Fans
  • Childrens Activities
  • Communal Facilities
  • Golf Cart
  • Golf Resort
  • Gym/Fitness Room
  • Private Garden
  • Private Pool
  • Restaurant
  • Sea view
  • Sound System
  • Spa
  • Staffed Villa
  • Tennis Court
  • TV
  • WaterSports
  • Wireless Internet
See more details...
Bedroom : 5
Bathroom : 5

Staff

  • Butler
  • Chef
  • Gardener
  • House keeper
  • Laundress

Rate

From To Min Stay Nightly Rate Weekly Rate
22-Nov-2025 28-Aug-2025 7 $3,087 USD $21,615 USD
18-Aug-2025 31-Oct-2025 7 $1,846 USD $12,925 USD
01-Nov-2025 21-Nov-2025 7 $2,149 USD $15,046 USD
29-Nov-2025 12-Dec-2025 7 $2,149 USD $15,046 USD
13-Dec-2025 19-Dec-2025 7 $3,865 USD $27,060 USD
20-Dec-2025 02-Jan-2026 7 $4,557 USD $31,900 USD
04-Jan-2026 06-Mar-2026 7 $3,396 USD $23,777 USD
07-Mar-2026 27-Mar-2026 7 $3,396 USD $23,777 USD
28-Mar-2026 24-Apr-2026 7 $3,396 USD $23,777 USD
25-Apr-2026 24-Jul-2026 7 $2,231 USD $15,620 USD
25-Jul-2026 30-Oct-2026 7 $2,031 USD $14,218 USD
31-Oct-2026 20-Nov-2026 7 $2,231 USD $15,620 USD
21-Nov-2026 28-Nov-2026 7 $3,993 USD $27,951 USD
28-Nov-2026 11-Dec-2026 7 $2,231 USD $15,620 USD
12-Dec-2026 18-Dec-2026 7 $3,630 USD $25,410 USD
19-Dec-2026 02-Jan-2027 7 $5,082 USD $35,574 USD
From To Min Stay Nightly Rate Weekly Rate
18-Aug-2025 31-Oct-2025 7 $1,857 USD $13,000 USD
01-Nov-2025 21-Nov-2025 7 $2,028 USD $14,200 USD
22-Nov-2025 28-Nov-2025 7 $3,630 USD $25,410 USD
29-Nov-2025 12-Dec-2025 7 $2,028 USD $14,200 USD
13-Dec-2025 19-Dec-2025 7 $3,300 USD $23,100 USD
20-Dec-2025 02-Jan-2026 7 $4,620 USD $32,340 USD
04-Jan-2026 06-Mar-2026 7 $3,630 USD $25,410 USD
07-Mar-2026 27-Mar-2026 7 $3,993 USD $27,951 USD
28-Mar-2026 24-Apr-2026 7 $3,630 USD $25,410 USD
25-Apr-2026 24-Jul-2026 7 $2,364 USD $16,551 USD
25-Jul-2026 30-Oct-2026 7 $2,042 USD $14,300 USD
31-Oct-2026 20-Nov-2026 7 $2,364 USD $16,551 USD
21-Nov-2026 28-Nov-2026 7 $3,993 USD $27,951 USD
28-Nov-2026 11-Dec-2026 7 $2,364 USD $16,551 USD
12-Dec-2026 18-Dec-2026 7 $4,252 USD $29,766 USD
19-Dec-2026 02-Jan-2027 7 $5,082 USD $35,574 USD

Rental rates are subject to 10.00 % TAX plus 7.50 % service charge.

Location

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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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