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Tryall Club - Oceana
From $3,531 - $9,600 / nt
From $3,531 - $9,600 / nt
We love this villa because...
its breathtaking hilltop views, seamless indoor-outdoor living, and resort-style amenities, offering the perfect blend of luxury and privacy.
Oceana ā€“ A Premier Jamaica Villa Rental Overlooking the Caribbean Sea
Perched atop the prestigious Garden Hill enclave, Oceana is a standout among Jamaica villa rentals. This modern, architect-designed estate offers uninterrupted views of the Caribbean Sea, Montego Bayā€™s coastline, and Jamaicaā€™s legendary sunsetsā€”making it an ideal destination for travelers seeking luxury villas in Jamaica that deliver both elegance and privacy.
Exceptional Caribbean Villa Living
Designed from the ground up to maximize both comfort and natural beauty, Oceana offers a seamless blend of indoor and outdoor spaces. This is island living redefined, where design, location, and service combine to offer a one-of-a-kind retreat.
What Makes Oceana Unique:
Infinity-edge pool: One of Tryallā€™s largest, it appears to flow directly into the sea.
Open-air architecture: Breezy living areas and wide patios create a relaxed, airy atmosphere.
Mesmerizing views: From sunrise to starlight, enjoy unmatched vistas across Jamaicaā€™s north coast.
Ideal for privacy: Separate living quarters offer privacy for families or groups.
Elegant Accommodations Across Three Buildings
This private estate includes multiple well-appointed residences, ideal for those searching for vacation villas in Jamaica that offer flexibility, space, and a resort-quality experience.
The Main House (Master Suite not included in 5-bedroom rental):
Luxurious suite with sweeping views, oversized soaking tub, and rainfall shower.
Fully accessible design for guests with mobility needs.
The Guest Cottage:
3 stylish en suite bedrooms with serene garden or sea views.
Cozy TV lounge ideal for relaxed evenings.
The Carriage House:
2 additional en suite bedrooms.
Private bar area.
Second pool with panoramic sea views.
Whether you choose the full villa or the 5-bedroom configuration, Oceana provides a unique experience not often found in holiday villas to rent in Jamaica.
Fitness & Wellness Amenities
Health-conscious travelers will enjoy the state-of-the-art fitness deck on the lower level, outfitted with:
Echelon smart gym equipment.
Stunning views to inspire your workouts.
Ideal for Families, Groups & Luxury Seekers
Oceana is a top choice for:
Families looking for spacious Jamaica family villa rentals.
Groups wanting Jamaica villas with pools and plenty of room to spread out.
Guests seeking exclusive villas in Jamaica with personalized service.
Vacationers prioritizing privacy and luxury in the Caribbean villa rental market.
Book Oceana ā€“ A Signature Luxury Villa in Jamaica
If you're searching for beachfront villas in Jamaica, private villa rentals in Jamaica, or simply a one-of-a-kind Caribbean escape, Oceana offers the perfect balance of natural beauty, high-end finishes, and world-class amenities.
This villa is also part of a premier collection of Jamaica villas to rent that cater to travelers seeking:
Jamaica vacation villas with staff.
Luxury villas to rent in the Caribbean.
Barbados villas for rent and other island retreats.
Explore More Villas in Jamaica and Beyond
Browse our handpicked selection of Caribbean villas, including luxury beachfront villas, villas in Jamaica with private chefs, and holiday villas to rent in Jamaica with pools and panoramic views. Your dream getaway starts here.
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 | $3,678 USD | $25,750 USD |
| 25-Jul-2026 | 30-Oct-2026 | 7 | $3,531 USD | $24,720 USD |
| 31-Oct-2026 | 20-Nov-2026 | 7 | $3,678 USD | $25,750 USD |
| 21-Nov-2026 | 28-Nov-2026 | 7 | $5,264 USD | $36,850 USD |
| 28-Nov-2026 | 11-Dec-2026 | 7 | $3,678 USD | $25,750 USD |
| 12-Dec-2026 | 18-Dec-2026 | 7 | $4,662 USD | $32,635 USD |
| 19-Dec-2026 | 02-Jan-2027 | 7 | $8,000 USD | $56,000 USD |
| 03-Jan-2027 | 12-Feb-2027 | 7 | $4,821 USD | $33,750 USD |
| 20-Feb-2027 | 05-Mar-2027 | 7 | $4,821 USD | $33,750 USD |
| 24-Apr-2027 | 23-Jul-2027 | 7 | $3,864 USD | $27,050 USD |
| 24-Jul-2027 | 29-Oct-2027 | 7 | $3,714 USD | $26,000 USD |
| 30-Oct-2027 | 19-Nov-2027 | 7 | $3,864 USD | $27,050 USD |
| 20-Nov-2027 | 26-Nov-2027 | 7 | $6,143 USD | $43,000 USD |
| 27-Nov-2027 | 10-Dec-2027 | 7 | $3,864 USD | $27,050 USD |
| 11-Dec-2027 | 18-Dec-2027 | 7 | $4,821 USD | $33,750 USD |
| 19-Dec-2027 | 02-Jan-2028 | 7 | $9,600 USD | $67,200 USD |
| From | To | Min Stay | Nightly Rate | Weekly Rate |
|---|---|---|---|---|
| 25-Apr-2026 | 24-Jul-2026 | 7 | $3,980 USD | $27,861 USD |
| 25-Jul-2026 | 30-Oct-2026 | 7 | $3,825 USD | $26,780 USD |
| 31-Oct-2026 | 20-Nov-2026 | 7 | $3,980 USD | $27,862 USD |
| 21-Nov-2026 | 28-Nov-2026 | 7 | $5,704 USD | $39,930 USD |
| 28-Nov-2026 | 11-Dec-2026 | 7 | $3,980 USD | $27,861 USD |
| 12-Dec-2026 | 18-Dec-2026 | 7 | $5,273 USD | $36,915 USD |
| 19-Dec-2026 | 02-Jan-2027 | 7 | $9,600 USD | $67,200 USD |
| 03-Jan-2027 | 12-Feb-2027 | 7 | $5,486 USD | $38,400 USD |
| 13-Feb-2027 | 19-Feb-2027 | 7 | $6,400 USD | $44,800 USD |
| 20-Feb-2027 | 05-Mar-2027 | 7 | $5,486 USD | $38,400 USD |
| 24-Apr-2027 | 29-Oct-2027 | 7 | $4,014 USD | $28,100 USD |
| 30-Oct-2027 | 19-Nov-2027 | 7 | $4,171 USD | $29,200 USD |
| 20-Nov-2027 | 26-Nov-2027 | 7 | $6,143 USD | $43,000 USD |
| 27-Nov-2027 | 10-Dec-2027 | 7 | $5,986 USD | $41,900 USD |
| 11-Dec-2027 | 18-Dec-2027 | 7 | $5,293 USD | $37,050 USD |
| 19-Dec-2027 | 02-Jan-2028 | 7 | $9,600 USD | $67,200 USD |
Plan Your Trip
Amenities
- Air Conditioned bedrooms
- Communal Facilities
- Golf Cart
- Golf Resort
- Gym/Fitness Room
- Office
- Outdoor Jacuzzi
- Private Garden
- Private Pool
- Restaurant
- Sea view
- Sound System
- Spa
- Staffed Villa
- TV
- Wireless Internet
Room Details :
Bedroom : 6
Bathroom : 6
Staff
- Butler
- Chef
- Gardener
- House keeper
- House Manager
- Housekeeper / Maid
- Laundress
- Maid/Laundress
Additional Information:
Rates - No rates from March 7th 2026 - April 24th 2026 - Blocked out as N/A. - JP
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
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 youā€™re seeking a beachfront villa, a private pool retreat, or a family-friendly holiday home near Jamaicaā€™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 Jamaicaā€™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!
