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 – Exclusive Jamaica Vacation Villa at Tryall Club

Stunning Hilltop Luxury in Jamaica

Overlook Villa is a private hillside escape located within the prestigious Tryall Club, offering some of the most breathtaking views of the Caribbean Sea. Surrounded by vibrant tropical gardens, palm trees, and cooling breezes, this villa provides the perfect setting for a luxury Jamaica holiday villa. Guests can reach the club’s private beach, golf course, tennis courts, and spa with ease, whether walking or using a golf cart.

Villa Features

  • 5 elegant bedrooms accommodating up to 10 guests.

  • Open-plan living spaces designed to capture island breezes.

  • A spectacular heated infinity pool with jacuzzi platforms and a tranquil fountain.

  • Elevated hillside setting for privacy and peace.

  • Direct access to Tryall Club amenities including golf, tennis, and wellness facilities.

Dedicated Staff for a Seamless Stay

This private villa in Jamaica comes fully staffed to ensure every detail of your stay is effortless:

  • Professional butler.

  • Personal chef to prepare tailor-made menus.

  • Housekeeper and laundress.

  • Gardener to maintain the grounds.

From custom dining experiences to activity planning, your villa team ensures a truly memorable Caribbean escape.

Amenities & Comforts

  • Outdoor dining terrace and indoor air-conditioned dining room.

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

  • Authentic Caribbean décor enhanced with modern touches.

Why We Recommend Overlook Villa

Ideal for families, couples, or groups, Overlook is perfect for those seeking exclusive villas in Jamaica that combine privacy, luxury, and easy access to world-class amenities. Guests can relax by the pool, explore the island, or enjoy a cocktail at sunset before gathering for dinner under the stars.

Perfect Choice For

  • Travelers searching for Jamaica villas with staff.

  • Families seeking spacious Caribbean vacation villas.

  • Groups looking for luxury villas in Jamaica with pools.

  • Holidaymakers who want both hillside seclusion and beach access.

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
  • 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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