Tryall Club - Oceana
6 Bedrooms
From $3,531 USD - $9,600 USD / nt
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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 – Luxury Jamaica Villa Rental at Tryall Club
A Hilltop Retreat with Panoramic Caribbean Views
Overlook Villa is one of the most sought-after Jamaica villas within the exclusive Tryall Club. Perched high on the hillside, this private villa offers sweeping views of the Caribbean Sea, surrounded by lush tropical gardens, towering palms, and vibrant blooms. Guests enjoy easy access—by foot or golf cart—to the Tryall Club’s world-class amenities, making it an ideal choice for luxury villas in Jamaica and Caribbean villa rentals.
Highlights of Overlook Villa
5 spacious bedrooms – accommodates up to 10 guests.
Elegant Caribbean-inspired décor with open, breezy living spaces.
Expansive heated infinity pool with jacuzzi platforms and a tranquil fountain.
Nestled in a peaceful hillside setting for total privacy.
Access to Tryall Club’s golf course, tennis courts, spa, and private beach.
Private Villa Experience with Full Staff
Overlook offers the ultimate Jamaica private villa rental experience. Your stay is fully supported by a professional villa team:
Butler.
Private chef.
Housekeeper.
Laundress.
Gardener.
Your chef will craft personalized menus, while your butler arranges daily activities, from tee times to island excursions.
Modern Comforts & Amenities
Air-conditioned dining room and outdoor dining under the stars.
Wi-Fi, surround sound, and Starlink-connected SMART TVs with North American channels.
Seamless blend of traditional island charm and modern convenience.
Why Choose Overlook Villa?
Whether you’re looking for exclusive villas in Jamaica, family villa rentals, or luxury Caribbean villas, Overlook is designed for relaxation and connection. Guests can:
Wake up to refreshing sea breezes.
Spend the day golfing, playing tennis, or lounging poolside.
End the evening with sunset cocktails and an unforgettable dinner.
Perfect For
Families and groups seeking spacious holiday villas to rent in Jamaica.
Travelers wanting beachfront villa access with hillside privacy.
Guests looking for luxury Jamaica vacation villas with dedicated staff.
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
Special Offer(s):
Stay 4 nights and pay for only 3, stay 7 nights and pay for only 5! Valid for stays between 06 June and 31 October 2026. Must be booked by 31 July 2026. Call or message for latest availability or further information.
Rates
| From | To | Min Stay | Nightly Rate | Weekly Rate |
|---|---|---|---|---|
| 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 |
| 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-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 |
| 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
