Villa Tradewinds at the Tryall Club on Jamaica is an island-style Montego Bay home perched right at the edge of the turquoise waters of the Caribbean Sea. The villa features 300 feet of waterfront on the desirable northern coast of the island. Two lush acres of tropical vegetation form the backdrop for this outstanding villa, and an expansive grassy lawn to the east is ideal as a children's play area.
Villa Tradewinds is tastefully furnished with comfortable seating areas, creating the ambiance of a true home away from home. The entertainment center in the living room offers cable TV, a library of CDs, videos and a surround sound system, making it a natural gathering place for friends and family. The ten glass paneled doors open wide to the verandah and pool terrace where comfy chaise lounges overlook the pool and the sea. A wet bar adjoining the living room is convenient for a drink before dinner.
Your personal chef will prepare delicious home cooked meals served under a delightful chandelier within view of panoramic seascapes and a lighted garden of tropical plants. Or, if you prefer, take your meals outdoors on the terrace where you will enjoy the cooling tradewinds that are the hallmark of the villa and the sounds of the gently lapping sea. A series of stone steps leads from the terrace to the calm water that invites swimming and snorkeling. On windy days, try your hand at windsurfing.
The Tryall Club Membership: complimentary beach, pickle ball, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, Usain Bolt Games Room for all ages, jogging trail, afternoon tea & Manager's Cocktail Party every Monday night. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports & Reggae Night on the Beach Thursday night.
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Dues cost of US$170 (plus a 15% service charge) per week for each guest 16 years and over, or US$34 (plus a 15% service charge) per day per person for stays of less than 7 days. Children between the ages of 13 and 15 are at a discounted rate of 50% plus a 15% service charge. For children 12 years and younger, the Temporary Membership Dues are complimentary.
Please Note: Tryall Club membership is guaranteed for guests traveling through November 1, 2025.
***Please note that while we strive to maintain all amenities in perfect working condition, Jacuzzis and hot tubs cannot be guaranteed. This unit contains complex parts that may occasionally break down and can be challenging to replace promptly. We appreciate your understanding.
All bedrooms are equipped with A/C, ceiling fans, flat-screen TV and safes.
Main House
Bedroom 1: Master bedroom with a king-size bed, daybed, sitting area, desk, access to terrace, ocean view and en-suite bathroom with walk-in shower, vanity and WC. 2 guests maximum.
Bedroom 2: Bedroom with a king-size bed (can be made up as two single beds), connecting door to interior passageway leading to bedroom 3 and en-suite bath with walk-in shower, vanity and WC. 2 guests maximum.
Bedroom 3: Bedroom with a king-size bed (can be made up as two single beds), connecting door to interior passageway leading to bedroom 2 and en-suite bath with bathtub/shower combination, vanity and WC. 2 guests maximum.
Octagonal Cottage
Bedroom 4: Bedroom with a king-size bed (can be made up as two single beds), access to pool terrace, ocean view and en-suite bathroom with walk-in shower, outdoor shower, vanity and WC. 2 guests maximum.
- Air Conditioning - Bedrooms
- Alfresco Dining Area
- Beach Access
- Beach Towels
- Bed and Bath Linens
- Cable TV
- CD Player
- Ceiling Fans
- Chef Service
- Connected Bedrooms
- Daily Turndown Service
- DVD Player
- Film Library
- Fitness Room - Community Shared
- Golf (Nearby)
- Golf Cart
- Hair Dryer
- Internet
- Iron
- Kayak
- Kids Club
- Library
- Media Room
- On-Site Heliport
- Outdoor Grill
- Outdoor Shower
- Phone
- Playground
- Resort Privileges
- Secured Parking
- Table Tennis
- Tryall Club Membership
- View - Ocean/Sea
- Voltage - 110
- Wheelchair Accessible
- WiFi
- Butler/Host
- Chef/cook
- Gardener
- Housekeeper(s)
- Laundress
- Pool Person
- Property Manager on Call
Suggested staff gratuity is 15% of the rental rate during low season and 10% of the rental rate during high season.
- Outdoor
- Private
- Reservation deposit is 30%. Full balance is due 90 days prior to arrival.
- Holiday/Festive Booking Condition: 50% deposit required. Balance due by August 1st.
- Thanksgiving Booking Condition: 50% deposit required. Balance due by August 1st.
- Cancellation Policy: General Conditions: For cancellations greater than 61 days prior to arrival, 25% of the deposit paid + US$300 admin fee is forfeited. Cancellations within 60 days, 100% of gross rental is forfeited. Thanksgiving Conditions: For cancellations greater than 91 days prior to arrival, 25% of the deposit paid + US$300 admin fee is forfeited. Cancellations within 90 days, 100% of gross rental is forfeited. Holidays/Festive Conditions: For cancellations greater than 121 days prior to arrival, 25% of the paid deposit + US$300 admin fee is forfeited. Cancellations within 120 days, 100% of gross rental is forfeited. Please note 7.5% Tryall Club fee is non-refundable.
- Check In / Check Out: 3pm / 11am
- Damage Deposit: Mandatory US$199.00 fee covering up to US$3000 worth of damage
- Children Welcome (all ages)
- No Pets Allowed
- No Smoking
- Club Membership
- Full capacity rate required during Thanksgiving week.
- Kids Club
- Provisions and groceries are not included
- Rates are set in US Dollars. Prices in other currencies may fluctuate.
- Staff gratuity is 10% of the gross rental rate in High Season, 15% in Low Season, divided among the staff members. Amount to be paid in cash at the villa.
- Utilities included
- Villa orientation
- Tryall Club Temporary Membership Fee per week - $170 + 15% tax per guest per day
- Tryall Club Temporary Membership Fee for stays of less than 7 days - $34 + 15% tax per guest per day
- Jamaica fee - US$ 50
- Mandatory US$199.00 fee covering up to US$3000 worth of damage
Once a vacation home is selected, the pampered adventure begins. Our concierge team will assist with creating a magical and immersive vacation experience. Our services include
- Arrival Logistics & Transfers *
- Chef and Catering Services *
- Excursions
- Experiences & Activities
- In Villa Spa Services *
- Private Charters *
- Provisioning/Pre-Stocking
- Rental Cars with Free Delivery *
- Rental Equipment (crib, kayak, etc)
- VIP Fast Track Arrivals *
While available for advanced requests, the concierge team connects with guests 30 days prior to arrival to coordinate arrivals and to reserve desired services and experiences. Guests with scheduled Christmas/New Year stays will be contacted 90 days prior to arrival.
For example, a 5 bedroom villa that offers a 3 bedroom rate will be the exclusive use of the guest but two bedrooms and their en-suite bathrooms will be locked off. Capacity is capped at 2 guests per bedroom.
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Escape to Paradise with Our Villa Promotion!
Book a 5-night stay or longer with a minimum of US$5000 rental rate, and we'll pamper you with a US$200 Concierge Credit that can be used towards a range of exclusive services to make your stay truly unforgettable.
Use Your US$200 Concierge Credit for:
- Spa Services: Relax and rejuvenate with a wide range of spa treatments right in the comfort of your villa. Indulge in massages, facials, and more.
- Charters: Set sail on a private yacht or boat charter and explore the pristine waters of your destination. Discover hidden coves, snorkel in crystal-clear waters, and soak up the sun in style.
- Tours: Explore the local culture and attractions with our curated tours. From historical sites to culinary adventures, we've got you covered.
- Excursions: Dive into thrilling adventures with our exciting excursions.
Don't miss out on this incredible opportunity to elevate your villa experience! Book your 5-night stay or longer and take advantage of our US$200 Concierge Credit.
Terms and Conditions:
- Promotion valid for new bookings made between January 31, 2024 and March 31, 2025.
- Not applicable for Holiday dates (December 20, 2025 to January 5, 2026)
- Concierge Credit is non-transferable and has no cash value.
- Concierge Credit does not apply to car rental or chef service.
- Services are subject to availability and must be booked in advance.
- Other terms and conditions may apply.
Offer ends: May 31, 2025
Offer cannot be combined with other offers | Offer based on availability | Minimum night stay required | Non-transferrable | No cash value | Promotion is only valid on new reservations | Black-out dates may apply | Rates subject to tax and service charge
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