About the property
Southwind Villa: A Classic West Indies Retreat with Timeless Soul
Perched high above the turquoise waters of Charlotte Amalie harbor, Southwind Villa welcomes you into a world where the elegance of the Old West Indies lingers in every detail. From the moment you arrive, there's a sense that time slows down here—that this is a place meant for unwinding, for reconnecting, and for savoring the beauty of simple, soulful island living.
The villa is rich in classic Caribbean architecture, with warm terra cotta tiles underfoot, arched doorways that catch the golden light, and shuttered windows that usher in soft breezes from the sea. Rattan and wicker furnishings, hand-carved wood pieces, and soft island hues create an atmosphere that's both nostalgic and inviting—echoing the grace and warmth of a classic era.
From morning coffee to sunset cocktails, the panoramic views are simply mesmerizing—watch from the open-air verandas as sailboats drift into the harbor, cruise ships light up the evening horizon, and tropical palms sway gently against an endless blue backdrop. A private pool terrace is tucked among lush greenery, offering a peaceful escape with stunning views.
While Southwind Villa feels like a retreat from the modern world, its comforts are anything but old-fashioned. Thoughtfully updated, the home includes high-speed Wi-Fi, smart TVs, air conditioning, and a fully equipped kitchen—all seamlessly integrated so that the charm of the villa remains untouched. Whether you're streaming a favorite shows after a beach day or catching up on a bit of work from the antique writing desk, you can stay as connected—or as blissfully unplugged—as you choose.
Southwind Villa is perfectly located just minutes from the shops, restaurants, and historic charm of downtown Charlotte Amalie, and a short drive from some of St. Thomas's most pristine beaches. But once you've settled into the rhythm of this home—its breezy verandas, soul-soothing views, and timeless spirit—you may find little reason to leave.
Come and experience the Caribbean and Old West Indies charm the way it was meant to be— warm, welcoming, unhurried, and unforgettable.
Confirmed guests will be required to sign a guest license/rental agreement and may be required to keep a credit card on file for incidentals
Have questions? Just ask! I've been hosting short term rentals in St. Thomas for more than 15 years - so I will make sure we find you the best property to suit your specific needs, plus we have many fantastic options to choose from!
Traveling with a larger group? Let us know and we will show you all the units nearby that are available for rental!
Why book with Prestige Luxury Villas?
- All of our properties undergo a 25-point inspection before arrival to make sure everything is working and in perfect order.
- 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! - We represent a large inventory of properties; If there is an emergency issue with your property, chances are you will never be left high and dry.
- We provide a 24/7 maintenance and an emergency hotline.
** There are extra guest fees after 10 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.
Southwind Villa: A Classic West Indies Retreat with Timeless Soul
Perched high above the turquoise waters of Charlotte Amalie harbor, Southwind Villa welcomes you into a world where the elegance of the Old West Indies lingers in every detail. From the moment you arrive, there's a sense that time slows down here—that this is a place meant for unwinding, for reconnecting, and for savoring the beauty of simple, soulful island living.
The villa is rich in classic Caribbean architecture, with warm terra cotta tiles underfoot, arched doorways that catch the golden light, and shuttered windows that usher in soft breezes from the sea. Rattan and wicker furnishings, hand-carved wood pieces, and soft island hues create an atmosphere that's both nostalgic and inviting—echoing the grace and warmth of a classic era.
From morning coffee to sunset cocktails, the panoramic views are simply mesmerizing—watch from the open-air verandas as sailboats drift into the harbor, cruise ships light up the evening horizon, and tropical palms sway gently against an endless blue backdrop. A private pool terrace is tucked among lush greenery, offering a peaceful escape with stunning views.
While Southwind Villa feels like a retreat from the modern world, its comforts are anything but old-fashioned. Thoughtfully updated, the home includes high-speed Wi-Fi, smart TVs, air conditioning, and a fully equipped kitchen—all seamlessly integrated so that the charm of the villa remains untouched. Whether you're streaming a favorite shows after a beach day or catching up on a bit of work from the antique writing desk, you can stay as connected—or as blissfully unplugged—as you choose.
Southwind Villa is perfectly located just minutes from the shops, restaurants, and historic charm of downtown Charlotte Amalie, and a short drive from some of St. Thomas's most pristine beaches. But once you've settled into the rhythm of this home—its breezy verandas, soul-soothing views, and timeless spirit—you may find little reason to leave.
Come and experience the Caribbean and Old West Indies charm the way it was meant to be— warm, welcoming, unhurried, and unforgettable.
Confirmed guests will be required to sign a guest license/rental agreement and may be required to keep a credit card on file for incidentals
Have questions? Just ask! I've been hosting short term rentals in St. Thomas for more than 15 years - so I will make sure we find you the best property to suit your specific needs, plus we have many fantastic options to choose from!
Traveling with a larger group? Let us know and we will show you all the units nearby that are available for rental!
Why book with Prestige Luxury Villas?
- All of our properties undergo a 25-point inspection before arrival to make sure everything is working and in perfect order.
- 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! - We represent a large inventory of properties; If there is an emergency issue with your property, chances are you will never be left high and dry.
- We provide a 24/7 maintenance and an emergency hotline.
** There are extra guest fees after 10 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.
Southwind Villa: A Classic West Indies Retreat with Timeless Soul
Perched high above the turquoise waters of Charlotte Amalie harbor, Southwind Villa welcomes you into a world where the elegance of the Old West Indies lingers in every detail. From the moment you arrive, there's a sense that time slows down here—that this is a place meant for unwinding, for reconnecting, and for savoring the beauty of simple, soulful island living.
The villa is rich in classic Caribbean architecture, with warm terra cotta tiles underfoot, arched doorways that catch the golden light, and shuttered windows that usher in soft breezes from the sea. Rattan and wicker furnishings, hand-carved wood pieces, and soft island hues create an atmosphere that's both nostalgic and inviting—echoing the grace and warmth of a classic era.
From morning coffee to sunset cocktails, the panoramic views are simply mesmerizing—watch from the open-air verandas as sailboats drift into the harbor, cruise ships light up the evening horizon, and tropical palms sway gently against an endless blue backdrop. A private pool terrace is tucked among lush greenery, offering a peaceful escape with stunning views.
While Southwind Villa feels like a retreat from the modern world, its comforts are anything but old-fashioned. Thoughtfully updated, the home includes high-speed Wi-Fi, smart TVs, air conditioning, and a fully equipped kitchen—all seamlessly integrated so that the charm of the villa remains untouched. Whether you're streaming a favorite shows after a beach day or catching up on a bit of work from the antique writing desk, you can stay as connected—or as blissfully unplugged—as you choose.
Southwind Villa is perfectly located just minutes from the shops, restaurants, and historic charm of downtown Charlotte Amalie, and a short drive from some of St. Thomas's most pristine beaches. But once you've settled into the rhythm of this home—its breezy verandas, soul-soothing views, and timeless spirit—you may find little reason to leave.
Come and experience the Caribbean and Old West Indies charm the way it was meant to be— warm, welcoming, unhurried, and unforgettable.
Confirmed guests will be required to sign a guest license/rental agreement and may be required to keep a credit card on file for incidentals
Have questions? Just ask! I've been hosting short term rentals in St. Thomas for more than 15 years - so I will make sure we find you the best property to suit your specific needs, plus we have many fantastic options to choose from!
Traveling with a larger group? Let us know and we will show you all the units nearby that are available for rental!
Why book with Prestige Luxury Villas?
- All of our properties undergo a 25-point inspection before arrival to make sure everything is working and in perfect order.
- 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! - We represent a large inventory of properties; If there is an emergency issue with your property, chances are you will never be left high and dry.
- We provide a 24/7 maintenance and an emergency hotline.
** There are extra guest fees after 10 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.
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.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jul 16, 2026 | $601 | Available | 2 |
| Jul 17, 2026 | $610 | Available | 2 |
| Jul 18, 2026 | $732 | Not Available | 3 |
| Jul 19, 2026 | $705 | Not Available | 3 |
| Jul 20, 2026 | $681 | Not Available | 3 |
| Jul 21, 2026 | $663 | Not Available | 3 |
| Jul 22, 2026 | $747 | Not Available | 3 |
| Jul 23, 2026 | $770 | Not Available | 3 |
| Jul 24, 2026 | $867 | Available | 2 |
| Jul 25, 2026 | $918 | Available | 2 |
| Jul 26, 2026 | $926 | Available | 2 |
| Jul 27, 2026 | $706 | Not Available | 3 |
| Jul 28, 2026 | $665 | Not Available | 3 |
| Jul 29, 2026 | $670 | Not Available | 3 |
| Jul 30, 2026 | $700 | Not Available | 3 |
| Jul 31, 2026 | $683 | Not Available | 3 |
| Aug 1, 2026 | $684 | Not Available | 3 |
| Aug 2, 2026 | $662 | Not Available | 3 |
| Aug 3, 2026 | $714 | Not Available | 2 |
| Aug 4, 2026 | $638 | Available | 2 |
| Aug 5, 2026 | $649 | Available | 2 |
| Aug 6, 2026 | $833 | Not Available | 3 |
| Aug 7, 2026 | $809 | Not Available | 3 |
| Aug 8, 2026 | $762 | Not Available | 3 |
| Aug 9, 2026 | $755 | Not Available | 3 |
| Aug 10, 2026 | $642 | Available | 3 |
| Aug 11, 2026 | $638 | Available | 3 |
| Aug 12, 2026 | $637 | Available | 3 |
| Aug 13, 2026 | $644 | Available | 3 |
| Aug 14, 2026 | $642 | Available | 3 |
| Aug 15, 2026 | $652 | Available | 3 |
| Aug 16, 2026 | $594 | Available | 3 |
| Aug 17, 2026 | $581 | Available | 3 |
| Aug 18, 2026 | $598 | Available | 3 |
| Aug 19, 2026 | $614 | Available | 3 |
| Aug 20, 2026 | $623 | Available | 3 |
| Aug 21, 2026 | $619 | Available | 3 |
| Aug 22, 2026 | $626 | Available | 3 |
| Aug 23, 2026 | $564 | Available | 3 |
| Aug 24, 2026 | $549 | Available | 3 |
| Aug 25, 2026 | $549 | Available | 3 |
| Aug 26, 2026 | $571 | Available | 3 |
| Aug 27, 2026 | $642 | Available | 3 |
| Aug 28, 2026 | $641 | Available | 3 |
| Aug 29, 2026 | $656 | Available | 3 |
| Aug 30, 2026 | $714 | Not Available | 5 |
| Aug 31, 2026 | $635 | Not Available | 5 |
| Sep 1, 2026 | $647 | Not Available | 5 |
| Sep 2, 2026 | $686 | Not Available | 5 |
| Sep 3, 2026 | $660 | Not Available | 5 |
| Sep 4, 2026 | $809 | Not Available | 5 |
| Sep 5, 2026 | $759 | Available | 3 |
| Sep 6, 2026 | $804 | Available | 3 |
| Sep 7, 2026 | $634 | Available | 3 |
| Sep 8, 2026 | $570 | Available | 3 |
| Sep 9, 2026 | $586 | Available | 3 |
| Sep 10, 2026 | $618 | Available | 3 |
| Sep 11, 2026 | $646 | Available | 3 |
| Sep 12, 2026 | $662 | Available | 3 |
| Sep 13, 2026 | $621 | Available | 3 |
| Sep 14, 2026 | $584 | Available | 3 |
| Sep 15, 2026 | $584 | Available | 3 |
| Sep 16, 2026 | $622 | Available | 3 |
| Sep 17, 2026 | $652 | Available | 3 |
| Sep 18, 2026 | $686 | Available | 3 |
| Sep 19, 2026 | $669 | Available | 3 |
| Sep 20, 2026 | $695 | Available | 3 |
| Sep 21, 2026 | $648 | Available | 3 |
| Sep 22, 2026 | $637 | Available | 3 |
| Sep 23, 2026 | $666 | Available | 3 |
| Sep 24, 2026 | $677 | Available | 3 |
| Sep 25, 2026 | $669 | Available | 3 |
| Sep 26, 2026 | $649 | Available | 3 |
| Sep 27, 2026 | $676 | Available | 3 |
| Sep 28, 2026 | $642 | Available | 3 |
| Sep 29, 2026 | $710 | Available | 3 |
| Sep 30, 2026 | $711 | Available | 3 |
| Oct 1, 2026 | $713 | Available | 3 |
| Oct 2, 2026 | $692 | Available | 3 |
| Oct 3, 2026 | $673 | Available | 3 |
| Oct 4, 2026 | $687 | Available | 3 |
| Oct 5, 2026 | $737 | Available | 3 |
| Oct 6, 2026 | $775 | Available | 3 |
| Oct 7, 2026 | $739 | Available | 3 |
| Oct 8, 2026 | $741 | Available | 3 |
| Oct 9, 2026 | $776 | Available | 3 |
| Oct 10, 2026 | $814 | Available | 3 |
| Oct 11, 2026 | $723 | Available | 3 |
| Oct 12, 2026 | $700 | Available | 3 |
| Oct 13, 2026 | $689 | Available | 3 |
| Oct 14, 2026 | $701 | Available | 3 |
Amenities
4.9 · 9 reviews
Wonderful property! Very peaceful and relaxing. Justin was a great host!
Really nice place to stay in St. Thomas. Beautiful view of Charlotte Amalie Harbor.
The pictures do NOT do that view justice. Insanely beautiful and the most friendly and helpful hosts. would book again 100 times over
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
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.