Windsong, Jamaica
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$714.29 / Nt
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Windsong

Montego Bay, Jamaica
4 BEDROOMS
3 Kings/2 Twins
1 Queen
4 BATHROOMS
4 En-suite
8 GUESTS
Children Welcome

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.

2024 Round Hill Membership is guaranteed for guests traveling through November 1, 2024.  Will not be renewed after November 1, 2024.
Round Hill offers a beach, pool, chaise lounges, towels, jogging trail, gift shop, logo shop, library with computer, bar, afternoon tea, Wednesday Manager's Cocktail Party, tennis courts, and unforgettable long sunsets from the waterfront terrace. For additional charges, members may enjoy the spa, Pineapple Kids Club, fitness center, salon, a range of water sports, and beach parties. 
Additional Amenities (fee required):
Kids’ Club: The cost for Pineapple Kid’s Club is US$27.50 daily per child. Children three years to twelve years old.  Children zero to three years old same cost but must be accompanied by a nanny. The hours of the Club are 9 am-5 pm. Lunch is not included (parents collect children for lunch).
- Gym: $50 per person per day for any guests in Round Hill Villas or villas with Round Hill membership (this fee should be paid at the front desk before using the gym)
- Spa, Salon, Range of water sports, Beach Parties

2025 Tryall Membership starting November 1st, 2024 and continuing through November 1st, 2025
Members may use most Club facilities at no charge except for 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.

Lot Size: 3 acres
There are no reviews for this property.

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
  • Round Hill Membership
  • Secured Parking
  • Spa
  • Tennis Court(s) - Nearby
  • View - Ocean/Sea
  • Voltage - 110
  • Wheelchair Accessible
  • WiFi
  • Butler/Host
  • Chef/cook
  • Driver
  • Gardener
  • Housekeeper(s)
  • Laundress
Housekeeping: Maid service 7 days a week
Chef : 3 meals per day
Cost of food and beverage is not included. Average budget is $70 per day per adult and $35 per day per child.

Suggested staff gratuity is 15% of the rental rate during low season and 10% of the rental rate during high season.
* Unless stated otherwise, the expenses for food and beverages are excluded and will be invoiced separately by the property.
  • Outdoor
  • Private
SEASON BEDROOMS DAILY WEEKLY
2024 Apr 16 to Nov 23 April 16, 2024 - November 23, 2024 (5 night minimum)
2 $715.00 $5,000.00
3 $961.00 $6,725.00
4 $1,135.00 $7,945.00
2024 Nov 23 to Dec 1 November 23, 2024 - December 1, 2024 (5 night minimum)
4 $1,904.00 $13,325.00
2024 Dec 1 to Dec 15 December 1, 2024 - December 15, 2024 (5 night minimum)
2 $715.00 $5,000.00
3 $961.00 $6,725.00
4 $1,135.00 $7,945.00
2024 Dec 15 to Dec 19 December 15, 2024 - December 19, 2024 (7 night minimum)
4 $1,904.00 $13,325.00
2024 Dec 19 to Dec 27 December 19, 2024 - December 27, 2024 (7 night minimum)
4 $2,223.00 $15,555.00
2024 Dec 27 to 2025 Jan 3 December 27, 2024 - January 3, 2025 (7 night minimum)
4 $2,223.00 $15,555.00
2025 Jan 3 to Apr 19 January 3, 2025 - April 19, 2025 (7 night minimum)
4 $1,904.00 $13,325.00
2025 Apr 19 to Apr 27 April 19, 2025 - April 27, 2025 (7 night minimum)
4 $1,904.00 $13,325.00
2025 Apr 27 to Nov 22 April 27, 2025 - November 22, 2025 (5 night minimum)
2 $794.00 $5,556.00
3 $1,068.00 $7,472.00
4 $1,262.00 $8,828.00
2025 Nov 22 to Nov 30 November 22, 2025 - November 30, 2025 (7 night minimum)
4 $1,904.00 $13,325.00
2025 Nov 30 to Dec 15 November 30, 2025 - December 15, 2025 (5 night minimum)
2 $794.00 $5,556.00
3 $1,068.00 $7,472.00
4 $1,262.00 $8,828.00
2025 Dec 15 to Dec 19 December 15, 2025 - December 19, 2025 (7 night minimum)
4 $1,904.00 $13,325.00
2025 Dec 19 to Dec 27 December 19, 2025 - December 27, 2025 (7 night minimum)
4 $2,223.00 $15,555.00
2025 Dec 26 to 2026 Jan 3 December 26, 2025 - January 3, 2026 (7 night minimum)
4 $2,223.00 $15,555.00
2024 Apr 16 to Nov 23 April 16, 2024 - November 23, 2024 (5 night minimum)
Bedrooms: 2
Daily: $715.00
Weekly: $5,000.00
Bedrooms: 3
Daily: $961.00
Weekly: $6,725.00
Bedrooms: 4
Daily: $1,135.00
Weekly: $7,945.00
2024 Nov 23 to Dec 1 November 23, 2024 - December 1, 2024 (5 night minimum)
Bedrooms: 4
Daily: $1,904.00
Weekly: $13,325.00
2024 Dec 1 to Dec 15 December 1, 2024 - December 15, 2024 (5 night minimum)
Bedrooms: 2
Daily: $715.00
Weekly: $5,000.00
Bedrooms: 3
Daily: $961.00
Weekly: $6,725.00
Bedrooms: 4
Daily: $1,135.00
Weekly: $7,945.00
2024 Dec 15 to Dec 19 December 15, 2024 - December 19, 2024 (7 night minimum)
Bedrooms: 4
Daily: $1,904.00
Weekly: $13,325.00
2024 Dec 19 to Dec 27 December 19, 2024 - December 27, 2024 (7 night minimum)
Bedrooms: 4
Daily: $2,223.00
Weekly: $15,555.00
2024 Dec 27 to 2025 Jan 3 December 27, 2024 - January 3, 2025 (7 night minimum)
Bedrooms: 4
Daily: $2,223.00
Weekly: $15,555.00
2025 Jan 3 to Apr 19 January 3, 2025 - April 19, 2025 (7 night minimum)
Bedrooms: 4
Daily: $1,904.00
Weekly: $13,325.00
2025 Apr 19 to Apr 27 April 19, 2025 - April 27, 2025 (7 night minimum)
Bedrooms: 4
Daily: $1,904.00
Weekly: $13,325.00
2025 Apr 27 to Nov 22 April 27, 2025 - November 22, 2025 (5 night minimum)
Bedrooms: 2
Daily: $794.00
Weekly: $5,556.00
Bedrooms: 3
Daily: $1,068.00
Weekly: $7,472.00
Bedrooms: 4
Daily: $1,262.00
Weekly: $8,828.00
2025 Nov 22 to Nov 30 November 22, 2025 - November 30, 2025 (7 night minimum)
Bedrooms: 4
Daily: $1,904.00
Weekly: $13,325.00
2025 Nov 30 to Dec 15 November 30, 2025 - December 15, 2025 (5 night minimum)
Bedrooms: 2
Daily: $794.00
Weekly: $5,556.00
Bedrooms: 3
Daily: $1,068.00
Weekly: $7,472.00
Bedrooms: 4
Daily: $1,262.00
Weekly: $8,828.00
2025 Dec 15 to Dec 19 December 15, 2025 - December 19, 2025 (7 night minimum)
Bedrooms: 4
Daily: $1,904.00
Weekly: $13,325.00
2025 Dec 19 to Dec 27 December 19, 2025 - December 27, 2025 (7 night minimum)
Bedrooms: 4
Daily: $2,223.00
Weekly: $15,555.00
2025 Dec 26 to 2026 Jan 3 December 26, 2025 - January 3, 2026 (7 night minimum)
Bedrooms: 4
Daily: $2,223.00
Weekly: $15,555.00

Rates based on 8 guests.
Extra Person Charge: $40.00 per night

Note: The rates above are subject to 0% Tax/Service Charge.
Payments accepted in US Dollars, Canadian Dollars, Euros, British Pound, Swiss Franc, Australian Dollars, New Zealand Dollars.
Major credit cards accepted in US Dollars.
Rates are subject to change without prior notice.

  • 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$149.00 fee covering up to US$2,500 worth of damage
  • Children Welcome (all ages)
  • No Pets Allowed
  • No Smoking
  • Club Membership
  • Full capacity rate required during Thanksgiving week.
  • Kids Club
  • Provisions and groceries are not included
  • Rates are set in US Dollars. Prices in other currencies may fluctuate.
  • Staff gratuity is 10% of the gross rental rate in High Season, 15% in Low Season, divided among the staff members. Amount to be paid in cash at the villa.
  • Utilities included
  • VAT taxes included in rates.
  • Villa orientation
  • Jamaica fee - US$ 50
  • Mandatory US$149.00 fee covering up to US$2,500 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

* at select destinations

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.

Advice, Answers and Tips
Explore our support articles for answers to your questions
Common Questions
Do we share the villa? click to close
No. You will not share the villa with another party. The villa is exclusively yours. If a larger villa offers a lower bedroom rate category, the villa will remain exclusively yours but the unrented bedrooms will be locked off.
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.
Are we protected from fraud? click to open
Yes. Isle Blue stands behind you throughout your entire vacation. Unlike other companies, each property we offer has been hand picked to ensure that our standards are met. All property managers are vetted and payments are required to be held in escrow. Our primary obligation is to ensure your satisfaction and to have an exceptionally memorable vacation.
Can you explain the reservation process? click to open
Once a reservation request is received, Isle Blue will request a contract from the property manager for your dates of interest. Once the dates are confirmed and contract is received from the property manager, a payment will be required to confirm your reservation.
Once a reservation is confirmed, a concierge will welcome you to the planning stages of your vacation to assist with arrival logistics, rental cars, transfers, and a host of concierge services.
Can we arrange an early check in? click to open
Early check in may be possible but is at the sole discretion of the property manager. Early check in permission may not be granted until 24 hours prior to arrival.
Can we arrange a late check out? click to open
A late check out is rarely granted due to the turnover needs of a villa. A late check out may only be granted 24 hours prior to your departure from the property and only when there is no check in scheduled on the day of your check out. If a late check out is urgently needed please contact us.
Are transfers to the property included? click to open
Select villas may include a one way or roundtrip airport transfer while others may provide an escort or meeting point. Arrival logistics will be handled by your dedicated concierge as well as other concierge needs. The property's transfer policy will be listed under the Policies section.
What to expect upon arrival? click to open
In general, a villa orientation will be provided along with a key turnover. During the orientation, information and instructions for the property will be provided. Emergency contact information will be provided. We are available 7 days a week to assist with any urgent needs.
The arrival procedures vary from villa to villa, select villas may include welcome provisioning while other properties will provide basic arrival information.
What is the cancellation policy? click to open
Since these vacation homes are one of a kind properties, the cancellation policy is strict. We highly recommend considering trip/travel insurance to protect against any unexpected cancellations or issues that may arise.
For more details, please visit Travel Protection
What happens if the property becomes unavailable after I reserve? click to open
In the unlikely event, the rented property becomes unavailable due to a major issue that may affect a guest's experience or a transfer of ownership, Isle Blue will coordinate with the property manager to find an alternate property of equal or superior standard that is subject to the guest's approval. If an alternate property is not acceptable to the guest, the guest will receive a full refund.
Do you accept credit cards (American Express, Mastercard, or Visa)? click to open
Yes, we accept all major credit cards. American Express, Visa, Mastercard and Discover are accepted. Please note that credit card charges may be subject to additional fees. There are no fees with payment by wire transfer or check.
In the near future, we expect to accept a greater variety of payment methods and currencies via Stripe.
Is housekeeping included? click to open
Housekeeping tends to be a standard among vacation homes but the frequency may vary greatly depending on the property manager’s standards. Most properties will offer daily housekeeping (except Sunday and holidays) while other villas may only provide a mid-week cleaning. Please refer to the Staff section to learn about the housekeeping frequency of the property.
Are towels and linens provided? click to open
Yes. The property will provide bath and pool towels along with linens. Towels and linens will be refreshed as needed.
Are toiletries and tissues provided? click to open
A property may supply an initial supply of soap, shampoo, toilet paper and paper towels but replenishment of supplies once exhausted may be the responsibility of the guest. Each property varies in their handling of toiletries and paper products.
Is a hair dryer available? click to open
A hair dryer should be available at the property. Upon arrival, please check the bathrooms or closet. Typically, a hair dryer is included in each bathroom.
Is an iron included? click to open
Typically yes, irons tend to be standard equipment for vacation homes. Please ask the property representative upon orientation for the location of the iron.

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.

PROMOTIONS

  • Promotion valid for new bookings made between September 1 and October 31, 2024.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 September 1 and October 31, 2024.
    - Not valid for Festive dates
    - 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: October 31, 2024

    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
(Updated Daily)
Date Unavailable Availability calendar may not reflect up to date reservation information.
Availability subject to change.

Location, Directions & Nearby Villas

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WHAT OUR GUESTS ARE SAYING

"Isle Blue is everything they say they are. They were a pleasure to deal with and were very responsive and informative. The pictures on their website are exactly what you end up getting and they provide full concierge service throughout your stay. My family and I had an amazing time and before we even returned home, we went to the Isle Blue website to check out their inventory for our next vacation. They really are just that good!"
Marc W.
Emvie
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