•
47 reviews
Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
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.
** There are extra guest fees beyond 12 guests.
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!
Bedroom 1
1 king bed, 1 full sofa
Bedroom 2
1 king bed, 1 full sofa
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Bedroom 1
1 king bed, 1 full sofa
Bedroom 2
1 king bed, 1 full sofa
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Jamie M.
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February 2026
Jeffrey H.
•
June 2025
Shelby T.
•
February 2025
St. Thomas, St. Thomas 00802, VI
St. Thomas, St. Thomas, VIFree cancellation up to 30 days before check-in. 50% refund up to 7 days before. No refund after that.
Pets not allowed
No smoking - fees will apply
Events allowed
Check-in after 4:00 pm
Check-out before 11:00 am
14 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Sep 20, 2026 | $2000 | Available |
| Sep 21, 2026 | $2000 | Available |
| Sep 22, 2026 | $2000 | Available |
| Sep 23, 2026 | $2000 | Available |
| Sep 24, 2026 | $2000 | Available |
| Sep 25, 2026 | $2000 | Available |
| Sep 26, 2026 | $2000 | Available |
| Sep 27, 2026 | $2000 | Available |
| Sep 28, 2026 | $2000 | Available |
| Sep 29, 2026 | $2000 | Available |
| Sep 30, 2026 | $2000 | Available |
| Oct 1, 2026 | $2000 | Available |
| Oct 2, 2026 | $2000 | Available |
| Oct 3, 2026 | $2000 | Available |
| Oct 4, 2026 | $2000 | Available |
| Oct 5, 2026 | $2000 | Available |
| Oct 6, 2026 | $2000 | Available |
| Oct 7, 2026 | $2000 | Not Available |
| Oct 8, 2026 | $2000 | Not Available |
| Oct 9, 2026 | $2000 | Not Available |
| Oct 10, 2026 | $2199 | Not Available |
| Oct 11, 2026 | $2000 | Not Available |
| Oct 12, 2026 | $2000 | Available |
| Oct 13, 2026 | $2000 | Available |
| Oct 14, 2026 | $2000 | Available |
| Oct 15, 2026 | $2000 | Available |
| Oct 16, 2026 | $2000 | Available |
| Oct 17, 2026 | $2000 | Available |
| Oct 18, 2026 | $2000 | Available |
| Oct 19, 2026 | $2000 | Available |
| Oct 20, 2026 | $2000 | Available |
| Oct 21, 2026 | $2000 | Available |
| Oct 22, 2026 | $2000 | Available |
| Oct 23, 2026 | $2070 | Available |
| Oct 24, 2026 | $2030 | Available |
| Oct 25, 2026 | $2000 | Available |
| Oct 26, 2026 | $2000 | Not Available |
| Oct 27, 2026 | $2000 | Not Available |
| Oct 28, 2026 | $2000 | Not Available |
| Oct 29, 2026 | $2026 | Not Available |
| Oct 30, 2026 | $2054 | Not Available |
| Oct 31, 2026 | $2000 | Not Available |
| Nov 1, 2026 | $2000 | Not Available |
| Nov 2, 2026 | $2000 | Not Available |
| Nov 3, 2026 | $2000 | Not Available |
| Nov 4, 2026 | $2000 | Not Available |
| Nov 5, 2026 | $2050 | Not Available |
| Nov 6, 2026 | $2139 | Not Available |
| Nov 7, 2026 | $2000 | Not Available |
| Nov 8, 2026 | $2085 | Not Available |
| Nov 9, 2026 | $2095 | Not Available |
| Nov 10, 2026 | $2107 | Not Available |
| Nov 11, 2026 | $2118 | Not Available |
| Nov 12, 2026 | $2135 | Not Available |
| Nov 13, 2026 | $2075 | Not Available |
| Nov 14, 2026 | $2000 | Not Available |
| Nov 15, 2026 | $2000 | Not Available |
| Nov 16, 2026 | $2000 | Not Available |
| Nov 17, 2026 | $2020 | Not Available |
| Nov 18, 2026 | $2000 | Not Available |
| Nov 19, 2026 | $2000 | Not Available |
| Nov 20, 2026 | $2000 | Available |
| Nov 21, 2026 | $2189 | Available |
| Nov 22, 2026 | $2300 | Available |
| Nov 23, 2026 | $2300 | Available |
| Nov 24, 2026 | $2300 | Not Available |
| Nov 25, 2026 | $2300 | Not Available |
| Nov 26, 2026 | $2300 | Not Available |
| Nov 27, 2026 | $2300 | Not Available |
| Nov 28, 2026 | $2300 | Not Available |
| Nov 29, 2026 | $2000 | Available |
| Nov 30, 2026 | $2000 | Available |
| Dec 1, 2026 | $2000 | Available |
| Dec 2, 2026 | $2000 | Available |
| Dec 3, 2026 | $2000 | Available |
| Dec 4, 2026 | $2000 | Available |
| Dec 5, 2026 | $2000 | Available |
| Dec 6, 2026 | $2000 | Available |
| Dec 7, 2026 | $2003 | Available |
| Dec 8, 2026 | $2000 | Available |
| Dec 9, 2026 | $2085 | Available |
| Dec 10, 2026 | $2109 | Available |
| Dec 11, 2026 | $2000 | Available |
| Dec 12, 2026 | $2184 | Not Available |
| Dec 13, 2026 | $2132 | Not Available |
| Dec 14, 2026 | $2102 | Not Available |
| Dec 15, 2026 | $2164 | Not Available |
| Dec 16, 2026 | $2165 | Not Available |
| Dec 17, 2026 | $2300 | Not Available |
| Dec 18, 2026 | $2300 | Not Available |
| Dec 19, 2026 | $2300 | Available |