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From $3,531 USD - $9,600 USD / nt

Oceana

Montego Bay  Jamaica
6
6
From $3,531 USD - $9,600 USD / nt
From $3,531 USD - $9,600 USD / 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 – Luxury Villa Retreat in Jamaica’s Scenic Hillside

Set high above the coastline on Garden Hill, Oceana is a modern sanctuary that redefines Caribbean villa living. Offering sweeping views over Montego Bay and the Caribbean Sea, this exquisite property is an exceptional choice for travelers seeking luxury villas in Jamaica that blend privacy, sophistication, and unforgettable scenery.


Caribbean Elegance with Unmatched Comfort

Oceana was designed for those who value peace, space, and refined design. Whether you're planning a family holiday or a group getaway, this Jamaica villa rental delivers elevated island living with every comfort taken care of.

Key Features of Oceana:

  • Expansive infinity pool with sea-to-sky views — one of the largest pools at Tryall.

  • Indoor-outdoor living with open-plan spaces and breezy terraces.

  • Panoramic Caribbean views from every corner of the villa.

  • Fully staffed service available for a seamless vacation experience.


Stylish Accommodation Across Three Residences

Oceana’s layout offers flexibility for larger groups or families, making it one of the most versatile private villa rentals in Jamaica.

Main Residence (Master Suite excluded in 5-bedroom bookings):

  • Elegant master bedroom with soaking tub and walk-in shower.

  • Designed with accessibility in mind.

  • Tranquil views over lush surroundings and the sea.

Guest Cottage:

  • 3 en suite guest rooms with island-inspired interiors.

  • TV lounge with tropical vistas.

Carriage House:

  • 2 additional en suite bedrooms.

  • Private lounge and minibar.

  • Second pool with breathtaking sea views.

Whether you're looking for Jamaica villas with staff or family-friendly villas in the Caribbean, Oceana checks every box.


Wellness with a View

Health and relaxation go hand in hand at Oceana. Guests have access to:

  • A private fitness deck.

  • High-end Echelon gym equipment.

  • Ocean-facing workout spaces for total rejuvenation.


Ideal for Families, Groups, and Luxury Getaways

Oceana is perfect for those in search of:

  • Jamaica family villa rentals with room to spread out.

  • Exclusive villas in Jamaica that provide total privacy.

  • Vacation villas in the Caribbean with a luxurious, home-like feel.

  • Jamaica vacation villas close to golf, beaches, and attractions.


Reserve Your Private Villa in Jamaica Today

Oceana is more than just a place to stay — it’s a full-service, luxury Caribbean escape. With two pools, five or six en suite bedrooms, and spectacular hilltop views, it stands out among villas in Jamaica with pools, as well as Jamaica villas to rent for both short- and long-term vacations.

Explore our full portfolio of holiday villas to rent in Jamaica, Barbados villas for rent, and luxury villas to rent in the Caribbean. Whether you’re looking for beachfront villas, private staffed homes, or group-friendly rentals, your dream Caribbean stay starts here.

If you are interested in renting this villa in jamaica 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

See more details...

Rate

FromToMin StayNightly RateWeekly Rate
29-Nov-202512-Dec-20257$3,571 USD$25,000 USD
13-Dec-202519-Dec-20257$4,357 USD$30,500 USD
20-Dec-202502-Jan-20267$7,142 USD$50,000 USD
04-Jan-202606-Mar-20267$4,585 USD$32,100 USD
25-Apr-202624-Jul-20267$3,678 USD$25,750 USD
25-Jul-202630-Oct-20267$3,531 USD$24,720 USD
31-Oct-202620-Nov-20267$3,678 USD$25,750 USD
21-Nov-202628-Nov-20267$5,264 USD$36,850 USD
28-Nov-202611-Dec-20267$3,678 USD$25,750 USD
12-Dec-202618-Dec-20267$4,662 USD$32,635 USD
19-Dec-202602-Jan-20277$8,000 USD$56,000 USD
FromToMin StayNightly RateWeekly Rate
29-Nov-202512-Dec-20257$3,864 USD$27,050 USD
13-Dec-202519-Dec-20257$4,857 USD$34,500 USD
20-Dec-202502-Jan-20267$8,571 USD$60,000 USD
04-Jan-202606-Mar-20267$5,044 USD$35,310 USD
25-Apr-202624-Jul-20267$3,980 USD$27,861 USD
25-Jul-202630-Oct-20267$3,825 USD$26,780 USD
31-Oct-202620-Nov-20267$3,980 USD$27,862 USD
21-Nov-202628-Nov-20267$5,704 USD$39,930 USD
28-Nov-202611-Dec-20267$3,980 USD$27,861 USD
12-Dec-202618-Dec-20267$5,273 USD$36,915 USD
19-Dec-202602-Jan-20277$9,600 USD$67,200 USD

Plan Your Trip

Ready for your Dream Escape?
Please contact us to confirm availability of your chosen villa and book your dates of stay.

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
Bedroom : 6
Bathroom : 6

    Staff

    • Butler
    • Chef
    • Gardener
    • House keeper
    • House Manager
    • Housekeeper / Maid
    • Laundress
    • Maid/Laundress

    Key Facts

    Additional Information:

    Rates - No rates from March 7th 2026 - April 24th 2026 - Blocked out as N/A. - JP


    Location

    HAVE QUESTIONS?

    USA/CANADA: +1 347 707 1195
    BARBADOS: +246-432-6307
    UK / INTERNATIONAL: +44 1978 368531

    Other Properties you may like

    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

    Live Chat


    A great way to communicate as we can answer your questions in real time. We are usually available 6 days a week between 9am and 8pm.

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