Windsong Villa stands as an impeccably designed and secluded residence, mere minutes away from Montego Bay's famed Round Hill estate.
This enchanting tropical villa embodies the essence of Jamaican living. Renowned for its expansive vistas, breezy interiors, verdant surroundings, and meticulously landscaped gardens, Windsong Villa emanates beauty and warmth, captivating from the exterior to the interior.
Blending seamlessly with its natural surroundings, the villa welcomes guests with an immediate sense of tranquility as they traverse the circular driveway shaded by a magnificent banyan tree adorned with hanging orchids. The courtyard beckons with its lush foliage and bubbling fountains, inviting guests to immerse themselves in the epitome of Caribbean lifestyle.
Perched atop a hill on the outskirts of Montego Bay, Windsong offers unparalleled views, allowing guests to marvel at the sunrise to the east over Montego Bay and relish in the breathtaking sunsets to the west above Round Hill and the verdant hills of Hanover, all while being caressed by the gentle trade winds.
Throughout the villa, soothing water features abound, creating an atmosphere of serenity and hospitality. The meticulously tended grounds showcase a rich variety of indigenous flora and fruit trees, the bounty of which graces the breakfast table when in season, inviting guests to leisurely explore Jamaica's botanical treasures.
Expertly managed by a seasoned team, Windsong ensures an experience that surpasses expectations. From personalized meal planning with the creative chef to attentive service and thoughtful recommendations, every aspect of your stay is meticulously curated for your utmost enjoyment.
Indulge in candlelit dinners indoors or opt for the relaxed ambience of the al fresco dining area overlooking the pool, where the poolside bar is always stocked with refreshing drinks and the sound system sets the mood for both indoor and outdoor gatherings.
The Tryall Club Membership:
All guests must pay a resort entry fee of US$34 per person per day plus a 15% tax to have access to the resort amenities at the Tryall Club. Children 13-15 years of age pay a discounted rate of 50% off plus 15% tax and children 12 & under are complimentary.
After paying the Temporary Membership Fee, members may use most Club facilities at no charge with the exception of the tennis shop, ball boys, bar & restaurant, spa, grocery, motorized water sports, nanny services, and golf. Complimentary amenities include the beach, non-motorized water sports, tennis, the excellent gym, the Hummingbird Kids Club, Great House afternoon tea, the Manager's Cocktail Party, and various special events.
Please Note: Tryall Club membership is guaranteed for guests traveling through November 1, 2025.
Bedroom 1: Main floor Master bedroom with a queen-size bed, A/C, TV, sound system, balconies and en-suite bathroom with bathtub, shower, double vanity and WC. 2 guests maximum.
Bedroom 2: Main floor bedroom with a king-size bed (can be made up as two single beds), A/C, sound system, balcony and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum.
Bedroom 3: Lower floor bedroom with a king-size bed (can be made up as two single beds), A/C, sound system, private terrace and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum.
Bedroom 4: Lower floor bedroom with a king-size bed (can be made up as two single beds), A/C, sound system, private terrace and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum.
- Air Conditioning - Bedrooms
- Alfresco Dining Area
- Beach Towels
- Bed and Bath Linens
- Cable TV
- CD Player
- Chef Service
- Children Welcome
- Coffee Maker
- Computer
- Daily Turndown Service
- DVD Player
- Film Library
- Hair Dryer
- Internet
- iPod Dock
- Iron
- Kids Club at additional charge
- Library
- Media Room
- Outdoor Bar
- Outdoor Grill
- Patio/Terrace
- Phone
- Secured Parking
- Spa
- Tennis Court(s) - Nearby
- Tryall Club Membership
- View - Ocean/Sea
- Voltage - 110
- Wheelchair Accessible
- WiFi
- Butler/Host
- Chef/cook
- Driver
- Gardener
- Housekeeper(s)
- Laundress
Complimentary driver & 10-seat van on 7-night reservations with full rate rental (4BR) - gas & gratuities are additional costs.
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 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 is forfeited. Cancellations within 90 days, 100% of gross rental is forfeited. Please note for Thanksgiving week all payment are non refundable for the following villas: Rio Chico, Lime-Acre, and Sundown. Holidays/Festive Conditions: For cancellations greater than 121 days prior to arrival, 25% of the deposit paid is forfeited. Cancellations within 120 days, 100% of gross rental is forfeited. Please note for Festive season all payment are non refundable for the following villas: Rio Chico, Lime-Acre, Sundown, Whispering Waters, Keela Wee, Happy Hour, and Sea Grapes.
- Check In / Check Out: 3pm / 11am
- Damage Deposit: Mandatory US$199.00 fee covering up to US$3000 worth of damage
- Children Welcome (all ages)
- No Pets Allowed
- No Smoking
- Club Membership
- Complimentary driver & 10-seat van on full capacity rate, 7-night stay (gas & gratuities are additional costs)
- Full capacity rate required during Thanksgiving week.
- Kids Club
- Provisions and groceries are not included
- Rates are set in US Dollars. Prices in other currencies may fluctuate.
- Staff gratuity is 10% of the gross rental rate in High Season, 15% in Low Season, divided among the staff members. Amount to be paid in cash at the villa.
- Utilities included
- VAT taxes included in rates.
- Villa orientation
- Jamaica fee - US$ 50
- Mandatory US$199.00 fee covering up to US$3000 worth of damage
- Tryall Club Temporary Membership Fee for stays of less than 7 days - $34 + 15% tax per guest per day
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.
Plan your dream destination wedding or special Caribbean event. The villa is available for wedding receptions and special events.
Maximum guests: 50 guests
Rental rates:
The villa requires seven nights minimum rental of villa at the full house rental rates. A $30 per person surcharge applies to outside guests (over double occupancy per bedroom) who attend a rehearsal dinner, the wedding reception, brunch, or any other hospitality event at the wedding villa.
Clients are also required to hire outside caterers as well as rent chairs, tables, tents, glasses, cutlery, and crockery.
Terms and conditions:
The villa does not allow unregistered guests to stay overnight. Overnight guests are restricted to 2 guests per rented bedroom and must be declared. If extra guests require accommodations, we recommend the rental of neighboring "sister" villas. For "sister" villas where additional guests are accommodated, there is a seven-night minimum in High Season and a five-night minimum in Low Season. Guests are responsible for the set-up and clean-up of the event. The event may not occur within 24 hours of departure. For example, with a Saturday departure guests must hold the event on Thursday or sooner.
Please contact our villa specialists to assist you in selecting the perfect wedding venue for your special occasion.
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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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