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Trade Winds Villa - 5 Bedroom , Montego Bay - Jamaica

About Trade Winds Villa - Montego Bay Jamaica

We know you will feel right at home with 5 Star services and will fall in love with Trade Winds Villa and Jamaica.

This is your time, and every day is what you make of it. Wake-up to a panoramic view of the Caribbean Sea, drink fresh brewed Blue Mountain coffee and enjoy a breakfast made to order by your personal chef. Plan your day to include a round of golf at one of three outstanding courses – Half Moon, White Witch or Cinnamon Hill – or lounge by the infinity edge pool with your every whim indulged.

Opt for accessing the amenities at the Half Moon Resort including sand and surf or a fully equipped gym or stay at the Villa and be pampered with onsite massage treatments. Browse the villa’s unique décor inspired by select pieces from who’s who in the local and Jamaican art scene. End your day in the company of friends and family for alfresco meals or indulge in a romantic dinner for two beneath the stars on the lower deck. Retire to your sea view room as early or late as you choose in the comfort of knowing you get to do it all over again tomorrow.

Located overlooking Half Moon Golf Course (10th hole) and set within the exclusive gated community of Spring Farm and yet only 10 minute drive from the Airport.

Description & Amenities:
*12,000 sq ft 5 bedroom fully staffed villa overlooking the Caribbean Sea.
*5 bedrooms, 5 en-suite luxury bathrooms all equipped with organic bathroom products, bathrobes, air conditioning and ceiling fans.
*40ft x 15ft Heated Infinity pool with 180 degree panoramic views.
*24 hour Concierge Services
*Butler, Chef, Housekeepers, Laundress and Gardener
*Secure Gated Community
*Includes one round trip airport transfer from Sangster International Montego Bay Airport
*Club Mobay VIP Service on arrival through Immigration and Customs to your waiting vehicle (7 night bookings)
*Complimentary Driver and vehicle for 7 night bookings (gas & $180. driver tip not included)
*Complimentary Luxury Resort Membership to Half Moon Resort
*Complimentary Access to 3 outstanding Championship Golf Courses Half Moon, White Witch and Cinnamon Hill (Guests pay only for Caddie & Cart)
*Indoor dining and outdoor dining options
*Two Stunning 40ft verandas with breathtaking 180 degree views.
*Two Outdoor TV Areas with 55” flat screen HD TV’s.
*Access to Apple, Netflix and Prime TV.
*Outdoor Bar with amazing views
*Foosball Table
*Outdoor Gas Grill
*Open Access to secure WIFi through the entire property including the pool
*SONOS Bluetooth Music System

Your complimentary membership to the luxury Half Moon Resort include:
*Golden sand beach with beach butlers.
*3 Swimming Pools
*9 floodlit Tennis Courts with professional coach (extra charge for pro lessons)
*6 Pickle Ball Courts
*Fitness Center/Gym
*Miniature Putting Green
*Kids Club (Additional charge)
*Horseback Riding (Additional charge)

Watersports - snorkeling, kayak, paddleboard, sailing, scuba, water skiing, tubing, parasailing, wakeboard, glass bottom boat (Additional Charge for water sports)
Gourmet Restaurants:
The Sugar Mill (a short walk from the villa), which boasts views of the lush tropical landscape in which sits a historic water wheel of the former Rose Hall Sugar Plantation.
The award winning Delmare Restaurant overlooking the sea which specializes in fresh fish and seafood with Italian Influences.

Bedroom Configuration:
All bedrooms are equipped with flat screen TVs and SONOS Bluetooth Speakers, Aqua Tunes, Air Conditioning and Ceiling Fans.

Main House
Master Bedroom Suite
- St Andrew - King Bed with large windows and bi-fold doors with amazing ocean views and direct access to large open veranda with comfortable outdoor wicker furniture. This veranda overlooks both the swimming pool and the ocean with beautiful views. Flat screen TV. Desk and seating area. Luxurious en-suite bathroom with shower, freestanding soaking tub and double vanity sinks.

Bedroom 2 - St Mary - King Bed, Flat Screen TV. Bright Large Bedroom with bi-fold doors with amazing ocean views and direct access to large open veranda with sumptuous outdoor wicker furniture. Luxurious en-suite bathroom with large walk in shower, soaking tub and double vanity sinks.

Bedroom 3 - St Thomas - Garden bedroom - Queen bed with en-suite bathroom with large walk in shower, and ample closet space. (same square footage as bedroom @ 2/ St, Mary) Flat Screen TV.

Bedroom 4 - St Catherine
- King Bed. Flat screen TV, luxurious bathroom with large shower, soaking tub, double vanity sinks and outdoor garden shower.

Bedroom 5 - Portland - King Bed. Flat screen TV, luxurious bathroom with large shower, soaking tub, double vanity sinks and outdoor garden shower.

There is a mini kitchen set up for coffee each morning in the cottage in case you like early morning coffee and do not want to go to the main villa.

The villa comes with a full-time Professional Chef, a personal butler, a gardener, two housekeepers and a laundress to take care of your requests allowing you to completely relax and have a perfect vacation.

We can also arrange massages treatments to help you completely unwind.
These can be taken at the villa on the covered private spa deck for you to enjoy the Caribbean breeze and views.

*Per Owner -
All Reservations must prepay 10% Gov Tax.
12.5% Staff Gratuity is paid at the end of your stay.

Click Here for:  Things To Do ~ Sites to See
Click Here for:  Restaurants in Montego Bay
Click Here for:  Golf Courses in Jamaica



Hi Vicki,  We enjoyed tradewinds, it was beautiful.  The chef was the same as our last time and it worked out very well!   Thank you! NM

Hi Vicki
I just wanted to let you know how wonderful the trip has been so far.
The chef at Trade Winds has done a fabulous job with our difficult requests! Really above and beyond.
I think you might be hearing from some of my friends who asked how we found this villa!
I’m pretty sure we will ask you to help us arrange another trip to this villa.

Dear Vicki, Our stay at Trade Winds was absolutely amazing and so were the staff!!! We loved everything about the villa and did not want to leave.
The food was 5 star and the staff made sure that every need/request was taken care of without complaint. They were so so friendly, it felt very much like family.
Thanks again for all of your help, it made the trip run smoothly. We will definitely be staying at Trade Winds again soon!

Trade Winds is a beautiful newly and tastefully decorated Villa with the charm of a fine boutique hotel and the comfort of your own backyard!
We spent hours just gazing at the amazing view of the sea, the sky and the ships passing by. Everything was wonderful! Thank you!

We loved the attention from your staff, so easy to get along with not to mention the pampering and delicious food.
Only problem is we didn’t want to leave Trade Winds, but when we did it was well worth it. Loved the golf and the beach!

The rooms have a spectacular view and are super comfortable. And the outdoor shower was an amazing experience!

The staff at the villa went above and beyond to make our stay perfect.
I was truly relaxed and at ease... Trade Winds is so peaceful.


  • King Bed
  • Patio / Balcony
  • Ceiling Fan
  • Air Conditioning
  • Cable TV
  • Bathtub w/Shower
  • Shower
  • Dual Sinks
  • Linens/Towels

COMMON AREA Living/Dining

  • Internet Access
  • Cable/Satellite TV
  • DVD Player
  • Patio / Balcony
  • Ceiling Fan
  • Bar
  • Indoor Dining
  • Outdoor Dining


  • King Bed
  • Patio / Balcony
  • Ceiling Fan
  • Air Conditioning
  • Cable TV
  • Bathtub w/Shower
  • Shower
  • Linens/Towels


  • Queen Bed
  • Ceiling Fan
  • Air Conditioning
  • Cable TV
  • Shower
  • Linens/Towels


  • King Bed
  • Patio / Balcony
  • Ceiling Fan
  • Air Conditioning
  • Cable TV
  • Bathtub w/Shower
  • Shower
  • Dual Sinks
  • Linens/Towels


  • King Bed
  • Patio / Balcony
  • Ceiling Fan
  • Air Conditioning
  • Cable TV
  • Bathtub w/Shower
  • Shower
  • Dual Sinks
  • Linens/Towels


  • Linens/Towels
  • Shower Only

Full Kitchen

  • Refrigerator
  • Cooking Range
  • Oven
  • Microwave Oven
  • Freezer
  • Coffee Maker
  • Blender
  • Juicer
  • Toaster

Property Amenities

  • Freshwater Pool (Private)
  • Full Staff
  • Daily Maid Service
  • Parking
  • Yard
  • Gazebo
  • Deck/Patio
  • Outdoor Dining
  • Barbeque Grill
  • Child Friendly
  • Bar
  • Washing Machine


  • Beach (driving distance)
  • Bicycling
  • Boat Rentals
  • Craft Market
  • Deep Sea Fishing
  • Duty-Free Shopping
  • Golf
  • Gym
  • Spa Facilities
  • Hiking
  • Horseback Riding
  • Kayaks
  • Pool Table
  • Sailing
  • Diving
  • Snorkeling
  • Sunfish Sailboats
  • Tennis
  • Tour Desk
  • Volleyball
  • Water Skiing
  • Wind Surfing
  • Jet Skis

Montego Bay, Jamaica

Rates in USD - Holidays may attract higher rates

WEEKLY RATES in US dollars

High Season December 15 - April 15

1-5 Bedroom $16,100


Low Season April 16 - December 14

1-5 Bedroom $14,000



1-5 Bedroom please inquire


Thanksgiving November 23 - November 30

1-5 Bedroom $19,250


Christmas December 21 - December 28

1-5 Bedroom $24,500


New Year December 28 - January 4

1-5 Bedroom $24,500

Owner adds 10% gov tax to all rates.

Owners asks 12.5% staff gratuity to be prepaid year round

Rates include a van and driver for the week (7 nights & More)

Comes with a full tank of gas and must be returned with a full tank of gas

** Gas is not included in the cost of the rental **

The driver gratuity of $160. not included in rental rate

Typically the van hold 8 persons with luggage for the airport transfers

We can add a luggage van if needed for $110. round trip

  • Book Now / Request Dates