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