St. Thomas, St. Thomas

Windsong

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14 guests
6 bedrooms
6 bathrooms
1000 sqft

Windsong is a private, secluded villa situated on a dramatic cliff edge on the East End of St.

  • Ocean view
  • Pool outdoor
  • Game Room
14 guests
6 bedrooms
6 bathrooms
1000 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation

    You can cancel your trip for up to 14 days prior to start.


About this property

Windsong is a private, secluded villa situated on a dramatic cliff edge on the East End of St. Thomas. This masterfully designed villa offers guests unparalleled and unobstructed ocean views and fantastic sunrises and sunsets. The location boasts 210-degree views of the British Virgin Islands, St. John, Christmas Cove, and St. Croix. Whether traveling with family or groups, Windsong's 6 bedrooms and 8 (6 ensuite, 2 half) baths ensure plenty of space and privacy as you enjoy all that St. Thomas has to offer. The villa is also able to accommodate 50 guests for receptions, weddings, and other special events. The spacious and open Great Room, Dining Room, and Kitchen are the villa's main gathering areas with additional outdoor chairs, sofas, and lounge chairs throughout the property. An outdoor dining table is located off the Great Room next to the pool. The kitchen is equipped with state-of-the-art appliances, granite countertops, and all the necessities your chef needs to prepare meals. Windsong's convenient East End location puts you within minutes of fantastic fine dining options at the St. Thomas Yacht Club, The Ritz-Carlton, and a number of restaurants in Red Hook. Red Hook and American Yacht Harbor are also home to numerous fishing charters, day-boat charters to the BVI, parasailing, snorkeling, and scuba tours. **All credit card payments are subject to transaction processing fees. In the event of a reservation cancellation, these fees are non-refundable, as they constitute direct costs incurred during the payment transaction.** Why book with Prestige Luxury Villas? 1.All of our properties undergo a 25-point inspection before arrival to make sure everything is working and in perfect order. 2.All of our properties are stocked with the basics, so you don’t have to sweat the small stuff! 3.The Prestige Luxury Villas team is comprised of long-time Virgin Island residents and well-seasoned travelers that provide you with accommodations and trip planning to meet your specific needs. We offer all our guests a full-service concierge, free of charge! Whether you’re looking for exhilarating adventure or peaceful relaxation, on land, at sea, or in the air, our complimentary Concierge Service will help ensure you have the Caribbean vacation you’ve been daydreaming about! 4.We represent a large inventory of properties; If there is an emergency issue with your property, you will never be left high and dry. 5.We provide a 24/7 maintenance and emergency hotline. Travelers who cancel at least 60 days before check-in will get back 100% of the amount they've paid, less any/all 3rd party transaction or processing fees where applicable. Cancellations made between 30 and 60 days prior to beginning of rental forfeit the 50% deposit made at the time of the booking, less any/all 3rd party transaction or processing fees wherever applicable. Cancellations made less than 30 days prior to beginning of stay forfeit the total amount due for the duration of the stay. The property is 100% private and for your use exclusively. Windsong is located on Deck Point, a gated, private peninsula on the east end of St. Thomas. Close to St. Thomas Yacht Club and only a 5-minute drive to Red Hook, which features many restaurants, shops, a marina, and the ferry to the BVI and St. John! We suggest renting a vehicle; however, we are happy to arrange other transportation if you’d like. We offer all our guests a full-service concierge, free of charge!

Windsong is a private, secluded villa situated on a dramatic cliff edge on the East End of St. Thomas. This masterfully designed villa offers guests unparalleled and unobstructed ocean views and fantastic sunrises and sunsets. The location boasts 210-degree views of the British Virgin Islands, St. John, Christmas Cove, and St. Croix. Whether traveling with family or groups, Windsong's 6 bedrooms and 8 (6 ensuite, 2 half) baths ensure plenty of space and privacy as you enjoy all that St. Thomas has to offer. The villa is also able to accommodate 50 guests for receptions, weddings, and other special events. The spacious and open Great Room, Dining Room, and Kitchen are the villa's main gathering areas with additional outdoor chairs, sofas, and lounge chairs throughout the property. An outdoor dining table is located off the Great Room next to the pool. The kitchen is equipped with state-of-the-art appliances, granite countertops, and all the necessities your chef needs to prepare meals. Windsong's convenient East End location puts you within minutes of fantastic fine dining options at the St. Thomas Yacht Club, The Ritz-Carlton, and a number of restaurants in Red Hook. Red Hook and American Yacht Harbor are also home to numerous fishing charters, day-boat charters to the BVI, parasailing, snorkeling, and scuba tours. **All credit card payments are subject to transaction processing fees. In the event of a reservation cancellation, these fees are non-refundable, as they constitute direct costs incurred during the payment transaction.** Why book with Prestige Luxury Villas? 1.All of our properties undergo a 25-point inspection before arrival to make sure everything is working and in perfect order. 2.All of our properties are stocked with the basics, so you don’t have to sweat the small stuff! 3.The Prestige Luxury Villas team is comprised of long-time Virgin Island residents and well-seasoned travelers that provide you with accommodations and trip planning to meet your specific needs. We offer all our guests a full-service concierge, free of charge! Whether you’re looking for exhilarating adventure or peaceful relaxation, on land, at sea, or in the air, our complimentary Concierge Service will help ensure you have the Caribbean vacation you’ve been daydreaming about! 4.We represent a large inventory of properties; If there is an emergency issue with your property, you will never be left high and dry. 5.We provide a 24/7 maintenance and emergency hotline. Travelers who cancel at least 60 days before check-in will get back 100% of the amount they've paid, less any/all 3rd party transaction or processing fees where applicable. Cancellations made between 30 and 60 days prior to beginning of rental forfeit the 50% deposit made at the time of the booking, less any/all 3rd party transaction or processing fees wherever applicable. Cancellations made less than 30 days prior to beginning of stay forfeit the total amount due for the duration of the stay. The property is 100% private and for your use exclusively. Windsong is located on Deck Point, a gated, private peninsula on the east end of St. Thomas. Close to St. Thomas Yacht Club and only a 5-minute drive to Red Hook, which features many restaurants, shops, a marina, and the ferry to the BVI and St. John! We suggest renting a vehicle; however, we are happy to arrange other transportation if you’d like. We offer all our guests a full-service concierge, free of charge!

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Dec 12, 2025$1,795Not Available5
Dec 13, 2025$1,795Not Available5
Dec 14, 2025$1,795Not Available5
Dec 15, 2025$1,795Not Available5
Dec 16, 2025$1,795Not Available5
Dec 17, 2025$1,795Not Available5
Dec 18, 2025$1,795Not Available5
Dec 19, 2025$1,795Not Available5
Dec 20, 2025$1,795Not Available5
Dec 21, 2025$1,795Not Available5
Dec 22, 2025$1,795Not Available5
Dec 23, 2025$1,795Not Available5
Dec 24, 2025$1,795Not Available5
Dec 25, 2025$1,795Not Available5
Dec 26, 2025$1,795Available3
Dec 27, 2025$1,795Available3
Dec 28, 2025$1,795Available3
Dec 29, 2025$1,795Not Available3
Dec 30, 2025$1,795Not Available5
Dec 31, 2025$1,795Not Available5
Jan 1, 2026$1,795Not Available5
Jan 2, 2026$1,795Not Available5
Jan 3, 2026$1,795Not Available5
Jan 4, 2026$1,795Not Available5
Jan 5, 2026$1,795Available3
Jan 6, 2026$1,795Available3
Jan 7, 2026$1,795Available3
Jan 8, 2026$1,795Not Available3
Jan 9, 2026$1,795Not Available5
Jan 10, 2026$1,795Not Available5
Jan 11, 2026$1,795Not Available5
Jan 12, 2026$1,795Available3
Jan 13, 2026$1,795Available3
Jan 14, 2026$1,795Available3
Jan 15, 2026$1,795Not Available3
Jan 16, 2026$1,795Not Available5
Jan 17, 2026$1,795Not Available5
Jan 18, 2026$1,795Not Available5
Jan 19, 2026$1,795Not Available5
Jan 20, 2026$1,795Not Available5
Jan 21, 2026$1,795Not Available5
Jan 22, 2026$1,795Available2
Jan 23, 2026$1,795Available2
Jan 24, 2026$1,795Not Available2
Jan 25, 2026$1,795Not Available5
Jan 26, 2026$1,795Not Available5
Jan 27, 2026$1,795Not Available5
Jan 28, 2026$1,795Not Available5
Jan 29, 2026$1,795Not Available5
Jan 30, 2026$1,795Not Available5
Jan 31, 2026$1,795Available5
Feb 1, 2026$1,795Available5
Feb 2, 2026$1,795Available5
Feb 3, 2026$1,795Available5
Feb 4, 2026$1,795Available5
Feb 5, 2026$1,795Available5
Feb 6, 2026$1,795Available5
Feb 7, 2026$1,795Available5
Feb 8, 2026$1,795Available5
Feb 9, 2026$1,795Available5
Feb 10, 2026$1,795Available5
Feb 11, 2026$1,795Available5
Feb 12, 2026$1,795Available5
Feb 13, 2026$1,795Available5
Feb 14, 2026$1,795Available5
Feb 15, 2026$1,795Available5
Feb 16, 2026$1,795Available5
Feb 17, 2026$1,795Available5
Feb 18, 2026$1,795Available5
Feb 19, 2026$1,795Available5
Feb 20, 2026$1,795Available5
Feb 21, 2026$1,795Available5
Feb 22, 2026$1,795Not Available5
Feb 23, 2026$1,795Not Available5
Feb 24, 2026$1,795Not Available5
Feb 25, 2026$1,795Not Available5
Feb 26, 2026$1,795Not Available5
Feb 27, 2026$1,795Not Available5
Feb 28, 2026$1,795Not Available5
Mar 1, 2026$1,795Available4
Mar 2, 2026$1,795Available5
Mar 3, 2026$1,795Available5
Mar 4, 2026$1,795Available5
Mar 5, 2026$1,795Available5
Mar 6, 2026$1,795Available5
Mar 7, 2026$1,795Available5
Mar 8, 2026$1,795Available5
Mar 9, 2026$1,795Available5
Mar 10, 2026$1,795Available5
Mar 11, 2026$1,795Available5
Mar 12, 2026$1,795Available5

Top notch amenities

GUEST FAVORITES

Ocean view
Pool outdoor
Game Room
Patio
Balcony
Garden
Sound system
Wifi
Free parking

Where you'll sleep



Explore St. Thomas, St. Thomas

Discover St. Thomas’s captivating blend of Caribbean allure and vibrant activity. Indulge in fine dining steps away at Sunset Grille at Secret Harbour, or explore the marine wonders of Coral World Ocean Park, just a short drive. Minutes away, enjoy the lively ambiance of Bolongo Bay Beach Resort, or catch a ferry from the Cruz Bay Ferry Dock for island adventures. For breathtaking vistas and unique shopping, Skyride to Paradise Point and Mongoose Junction are both within easy reach.

Things to know

Here are some things which you should know before booking Windsong

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
14 guests maximum
Pets not allowed
Events require approval

Cancellation policy

This property follows Tom Fallenstein St Thomas’s standard cancellation policy.