Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds

Tradewinds on the Sea

Montego Bay , Tryall  Jamaica
4
4
Add to Favourites
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
Tradewinds
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...
its rare private beach, breathtaking ocean views, and the perfect blend of Caribbean charm with modern luxury.

Tradewinds on the Sea – Luxury Beachfront Villa in Jamaica

Tradewinds on the Sea is a stunning luxury Jamaica villa rental set directly on the waterfront within the world-renowned Tryall Club. One of the few properties to offer its own private beach (depending on the tide), it combines timeless Caribbean charm with modern luxury for a truly unforgettable escape.


Villa Highlights

  • 4 elegant bedrooms accommodating up to 8 guests.

  • Private beach access for a secluded, exclusive experience.

  • Oceanfront swimming pool with integrated hot tub.

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

  • Open-plan living spaces with sweeping sea views.

  • Expansive lawn and shaded lounging areas.


Relaxed Caribbean Style

Built on one level and complemented by a separate guest cottage, Tradewinds enjoys prime sea frontage and beautifully landscaped gardens. Soft, serene interiors in coastal blues and greens echo the natural beauty outside.

Inside you’ll find:

  • A spacious lounge and dining area with panoramic views.

  • A media room for entertainment.

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


Luxurious Bedrooms & Bathrooms

Each of the villa’s four bedrooms offers a private en-suite and spectacular sea views:

  • Three bathrooms with outdoor showers and air-conditioning.

  • One bathroom with a bathtub and shower.

  • The master suite includes a private sitting area with bay views.


Ideal for Families or Groups

Perfect for those seeking exclusive villas in Jamaica, private villa rentals in the Caribbean, or a memorable Jamaica family villa, Tradewinds offers both privacy and exceptional service. The attentive staff ensures your stay is effortless and relaxing.


Location & Activities

As part of the prestigious Tryall Club, guests can enjoy world-class amenities including golf, tennis, fine dining, and a private beach club. The villa’s location also makes it easy to explore other beachfront villas in Jamaica and luxury Caribbean villas nearby.

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

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

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.

FOLLOW US

Subscribe to our Newsletter