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Tryall Club - Overlook
From $2,031 - $5,529 / nt
From $2,031 - $5,529 / nt
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
Rates
| From | To | Min Stay | Nightly Rate | Weekly Rate |
|---|---|---|---|---|
| 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 |
| 03-Jan-2027 | 12-Feb-2027 | 7 | $3,571 USD | $25,000 USD |
| 13-Feb-2027 | 19-Feb-2027 | 7 | $3,929 USD | $27,500 USD |
| 20-Feb-2027 | 05-Mar-2027 | 7 | $3,571 USD | $25,000 USD |
| 06-Mar-2027 | 02-Apr-2027 | 7 | $4,286 USD | $30,000 USD |
| 03-Apr-2027 | 23-Apr-2027 | 7 | $3,571 USD | $25,000 USD |
| 24-Apr-2027 | 23-Jul-2027 | 7 | $2,350 USD | $16,450 USD |
| 24-Jul-2027 | 29-Oct-2027 | 7 | $2,136 USD | $14,950 USD |
| 30-Oct-2027 | 19-Nov-2027 | 7 | $2,350 USD | $16,450 USD |
| 20-Nov-2027 | 26-Nov-2027 | 7 | $4,193 USD | $29,350 USD |
| 27-Nov-2027 | 10-Dec-2027 | 7 | $2,350 USD | $16,450 USD |
| 11-Dec-2027 | 18-Dec-2027 | 7 | $3,571 USD | $25,000 USD |
| 19-Dec-2027 | 02-Jan-2028 | 7 | $5,179 USD | $36,250 USD |
| From | To | Min Stay | Nightly Rate | Weekly Rate |
|---|---|---|---|---|
| 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 |
| 03-Jan-2027 | 12-Feb-2027 | 7 | $3,814 USD | $26,700 USD |
| 13-Feb-2027 | 19-Feb-2027 | 7 | $4,193 USD | $29,350 USD |
| 20-Feb-2027 | 05-Mar-2027 | 7 | $3,814 USD | $26,700 USD |
| 06-Mar-2027 | 02-Apr-2027 | 7 | $4,579 USD | $32,050 USD |
| 03-Apr-2027 | 23-Apr-2027 | 7 | $3,814 USD | $26,700 USD |
| 24-Apr-2027 | 23-Jul-2027 | 7 | $2,486 USD | $17,400 USD |
| 24-Jul-2027 | 29-Oct-2027 | 7 | $2,150 USD | $15,050 USD |
| 30-Oct-2027 | 19-Nov-2027 | 7 | $2,479 USD | $17,350 USD |
| 20-Nov-2027 | 26-Nov-2027 | 7 | $4,193 USD | $29,350 USD |
| 27-Nov-2027 | 10-Dec-2027 | 7 | $2,486 USD | $17,400 USD |
| 11-Dec-2027 | 18-Dec-2027 | 7 | $3,814 USD | $26,700 USD |
| 19-Dec-2027 | 02-Jan-2028 | 7 | $5,529 USD | $38,700 USD |
Plan Your Trip
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
Room Details :
Bedroom : 5
Bathroom : 5
Staff
- Butler
- Chef
- Gardener
- House keeper
- Laundress
Notice
Tryall Club Membership: $45 per adult per day, $25 per child aged 13-15 years per day. Children aged 12 years and under are complimentary.
Location
Have a Question?
USA/CANADA: +1 347 707 1195
BARBADOS: +246-432-6307
UK / INTERNATIONAL: +44 1978 368531
