St. Thomas, St. Thomas

Windsong

6 bedrooms8 beds6 baths14 guests4.8 (50)

About the 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.

** 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!

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!

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 16, 2026$2,450Not Available5
Jul 17, 2026$2,450Not Available5
Jul 18, 2026$2,450Not Available5
Jul 19, 2026$2,449Not Available5
Jul 20, 2026$2,450Not Available5
Jul 21, 2026$2,450Not Available5
Jul 22, 2026$2,450Not Available5
Jul 23, 2026$2,450Not Available5
Jul 24, 2026$2,394Not Available5
Jul 25, 2026$2,100Available3
Jul 26, 2026$2,100Available3
Jul 27, 2026$2,100Available3
Jul 28, 2026$2,100Available3
Jul 29, 2026$2,100Available3
Jul 30, 2026$2,100Available3
Jul 31, 2026$2,100Available3
Aug 1, 2026$2,000Available3
Aug 2, 2026$2,102Not Available5
Aug 3, 2026$2,050Not Available5
Aug 4, 2026$2,000Not Available5
Aug 5, 2026$2,000Not Available5
Aug 6, 2026$2,027Not Available5
Aug 7, 2026$2,039Not Available5
Aug 8, 2026$2,000Not Available5
Aug 9, 2026$2,000Available3
Aug 10, 2026$2,000Available3
Aug 11, 2026$2,000Available3
Aug 12, 2026$2,000Available3
Aug 13, 2026$2,000Available3
Aug 14, 2026$2,000Available3
Aug 15, 2026$2,000Available3
Aug 16, 2026$2,000Available3
Aug 17, 2026$2,000Available3
Aug 18, 2026$2,000Available3
Aug 19, 2026$2,000Available3
Aug 20, 2026$2,000Available3
Aug 21, 2026$2,000Available3
Aug 22, 2026$2,000Available3
Aug 23, 2026$2,000Available3
Aug 24, 2026$2,000Available3
Aug 25, 2026$2,000Available3
Aug 26, 2026$2,000Available3
Aug 27, 2026$2,000Available3
Aug 28, 2026$2,000Available3
Aug 29, 2026$2,000Available3
Aug 30, 2026$2,000Available3
Aug 31, 2026$2,000Available3
Sep 1, 2026$2,000Available3
Sep 2, 2026$2,000Available3
Sep 3, 2026$2,000Available3
Sep 4, 2026$2,000Available3
Sep 5, 2026$2,000Available3
Sep 6, 2026$2,000Available3
Sep 7, 2026$2,000Available3
Sep 8, 2026$2,000Available3
Sep 9, 2026$2,000Available3
Sep 10, 2026$2,000Available3
Sep 11, 2026$2,000Available3
Sep 12, 2026$2,000Available3
Sep 13, 2026$2,000Available3
Sep 14, 2026$2,000Available3
Sep 15, 2026$2,000Available3
Sep 16, 2026$2,000Available3
Sep 17, 2026$2,000Available3
Sep 18, 2026$2,000Available3
Sep 19, 2026$2,000Available3
Sep 20, 2026$2,000Available3
Sep 21, 2026$2,000Available3
Sep 22, 2026$2,000Available3
Sep 23, 2026$2,000Available3
Sep 24, 2026$2,000Available3
Sep 25, 2026$2,000Available3
Sep 26, 2026$2,000Available3
Sep 27, 2026$2,000Available3
Sep 28, 2026$2,000Available3
Sep 29, 2026$2,000Available3
Sep 30, 2026$2,000Available3
Oct 1, 2026$2,000Available3
Oct 2, 2026$2,000Available3
Oct 3, 2026$2,000Available3
Oct 4, 2026$2,000Available3
Oct 5, 2026$2,000Available3
Oct 6, 2026$2,000Available3
Oct 7, 2026$2,000Available3
Oct 8, 2026$2,000Available3
Oct 9, 2026$2,000Available3
Oct 10, 2026$2,300Available3
Oct 11, 2026$2,111Available3
Oct 12, 2026$2,110Available3
Oct 13, 2026$2,000Available3
Oct 14, 2026$2,000Available3

Amenities

Beachfront
Waterfront
Ocean view
Pool outdoor
Patio
Balcony
Wifi
Free parking

4.8 · 50 reviews

D
Donna
April 2026

Everything was just as we anticipated. Easy access and the views were amazing. Justin was always available via text when needed.

M
Matthew
March 2026

Our stay at this vacation house was nothing short of unforgettable. From the moment we arrived, we were struck by how beautiful the property was, every detail. Justin was a great host super responsive with anything we had questions about.

B
Brandon
March 2026

The house was absolutely beautiful with spectacular views. Justin was very helpful with suggestions and helped us get a second night that previously wasn't available. I highly recommend this property and highly recommend Justin and his team.

Where you'll be

St. Thomas, St. Thomas, 00802, VI

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
Events allowed with approval.

Safety & security

Check-in after 4:00 PM.
Check-out before 11:00 AM.
Maximum 14 guests.