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Tradewinds

Tradewinds on the Sea

Montego Bay , Tryall  Jamaica
4
4
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From $2,285 USD - $5,600 USD / nt

From $2,285 USD - $5,600 USD / nt

Plan Your Trip

HAVE QUESTIONS?

USA/CANADA: +1 347 707 1195
BARBADOS: +246-432-6307
UK / INTERNATIONAL: +44 1978 368531
From $2,285 USD - $5,600 USD / nt
We love this villa because...
We love Tradewinds on the Sea for its rare private beach, breathtaking ocean views, and the perfect blend of Caribbean charm with modern luxury.

Tradewinds on the Sea – Exclusive Jamaica Villa with Private Beachfront

Tradewinds on the Sea is a rare and exceptional Jamaica vacation villa, one of the few within the prestigious Tryall Club to offer its own private beach, depending on the tide. Perfectly positioned along the shoreline, it delivers breathtaking sea views and the quintessential Caribbean beachfront living experience.


Key Features

  • 4 luxurious bedrooms – accommodates up to 8 guests.

  • Private beach access for an exclusive stay.

  • Ocean-facing swimming pool with integrated hot tub.

  • Professional villa staff including Butler, Chef, Laundress, Housekeeper, Houseman, and Gardener.

  • Open-plan living spaces with panoramic sea views.

  • Spacious lawn and shaded areas for relaxation.


Stylish Caribbean Design

Tradewinds seamlessly blends traditional Caribbean charm with modern luxury. Built on one level with a separate guest cottage, the property features wide sea frontage and beautifully maintained gardens. Interiors are bright and airy, styled in serene coastal shades that mirror the ocean and sky.

Living spaces include:

  • A comfortable lounge and dining area with stunning views.

  • A media room for entertainment.

  • A large veranda with outdoor seating and a flat-screen TV.


Elegant Bedrooms & Bathrooms

Each bedroom at Tradewinds enjoys a sea view and a private en-suite bathroom:

  • Three bathrooms with outdoor showers and air conditioning.

  • One bathroom with a bathtub and shower.

  • The master suite features a private sitting area with a view of a sheltered bay.


Perfect for Families & Groups

Whether you are searching for Jamaica holiday villas, a private villa rental in the Caribbean, or a spacious family villa in Jamaica, Tradewinds offers the ideal setting. The full-time staff ensures every aspect of your holiday is taken care of, leaving you free to relax and enjoy.


Location

As part of the exclusive Tryall Club, guests have access to exceptional amenities including a championship golf course, tennis facilities, fine dining, and a beach club. Its location also offers easy access to other luxury villas in Jamaica and nearby Caribbean villa rentals.

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?

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 you’re seeking a beachfront villa, a private pool retreat, or a family-friendly holiday home near Jamaica’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 Jamaica’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!

Amenities

  • Air Conditioned bedrooms
  • Air Conditioning
  • Beach Club Facility
  • Beach Front
  • Communal Facilities
  • Gym/Fitness Room
  • Office
  • Outdoor Jacuzzi
  • Private Garden
  • Private Pool
  • Restaurant
  • Sea view
  • Shop
  • Short walk to beach
  • Sound System
  • Spa
  • Staffed Villa
  • Tennis Court
  • TV
  • WaterSports
  • Well Equipped Kitchen
  • Wireless Internet
See more details...
Bedroom : 4
Bathroom : 4

Staff

  • Butler
  • Chef
  • Gardener
  • House keeper
  • Laundress

Rate

From To Min Stay Nightly Rate Weekly Rate
11-Aug-2025 31-Oct-2025 7 $2,285 USD $16,000 USD
01-Nov-2025 21-Nov-2025 7 $2,414 USD $16,900 USD
22-Nov-2025 28-Nov-2025 7 $3,571 USD $25,000 USD
29-Nov-2025 12-Dec-2025 7 $2,414 USD $16,900 USD
13-Dec-2025 19-Dec-2025 7 $3,285 USD $23,000 USD
20-Dec-2025 02-Jan-2026 7 $5,000 USD $35,000 USD
04-Jan-2026 06-Mar-2026 7 $3,515 USD $24,610 USD
07-Mar-2026 27-Mar-2026 7 $3,614 USD $25,300 USD
28-Mar-2026 24-Apr-2026 7 $3,515 USD $24,610 USD
25-Apr-2026 25-Jul-2026 7 $2,414 USD $16,900 USD
25-Jul-2026 30-Oct-2026 7 $2,285 USD $16,000 USD
31-Oct-2026 20-Nov-2026 7 $2,414 USD $16,900 USD
21-Nov-2026 28-Nov-2026 7 $3,928 USD $27,500 USD
28-Nov-2026 11-Dec-2026 7 $2,414 USD $16,900 USD
12-Dec-2026 18-Dec-2026 7 $3,515 USD $24,610 USD
19-Dec-2026 02-Jan-2027 7 $5,600 USD $39,200 USD

Rental rates are subject to 10.00 % TAX plus 7.50 % service charge.

Location

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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

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