St. Thomas, St. Thomas

Southwind

5 bedrooms 8 beds 4 baths 12 guests 4.9 (9)

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? 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, chances are you will never be left high and dry. 5. We provide a 24/7 maintenance and an emergency hotline. **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? 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, chances are you will never be left high and dry. 5. We provide a 24/7 maintenance and an emergency hotline. **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) AvailabilityMin Stay (nights)
May 18, 2026$600Available2
May 19, 2026$604Available2
May 20, 2026$600Available2
May 21, 2026$762Not Available3
May 22, 2026$898Not Available3
May 23, 2026$901Not Available3
May 24, 2026$876Not Available3
May 25, 2026$1,018Not Available3
May 26, 2026$921Not Available3
May 27, 2026$809Not Available3
May 28, 2026$873Not Available3
May 29, 2026$870Not Available3
May 30, 2026$897Not Available3
May 31, 2026$868Not Available3
Jun 1, 2026$845Not Available3
Jun 2, 2026$805Not Available3
Jun 3, 2026$798Available3
Jun 4, 2026$926Not Available3
Jun 5, 2026$897Not Available3
Jun 6, 2026$904Not Available3
Jun 7, 2026$878Not Available3
Jun 8, 2026$962Available3
Jun 9, 2026$749Available3
Jun 10, 2026$767Available3
Jun 11, 2026$795Available3
Jun 12, 2026$773Available3
Jun 13, 2026$825Available3
Jun 14, 2026$818Available3
Jun 15, 2026$955Available3
Jun 16, 2026$831Available3
Jun 17, 2026$889Available3
Jun 18, 2026$899Available3
Jun 19, 2026$1,016Available3
Jun 20, 2026$903Available3
Jun 21, 2026$857Available3
Jun 22, 2026$809Available3
Jun 23, 2026$855Available3
Jun 24, 2026$1,030Available3
Jun 25, 2026$997Available3
Jun 26, 2026$1,160Available3
Jun 27, 2026$933Available3
Jun 28, 2026$919Available3
Jun 29, 2026$862Available3
Jun 30, 2026$860Available3
Jul 1, 2026$815Available3
Jul 2, 2026$1,009Available3
Jul 3, 2026$1,021Available3
Jul 4, 2026$1,018Available3
Jul 5, 2026$889Available3
Jul 6, 2026$895Available3
Jul 7, 2026$877Available3
Jul 8, 2026$922Available3
Jul 9, 2026$985Available3
Jul 10, 2026$951Available3
Jul 11, 2026$1,013Not Available3
Jul 12, 2026$1,206Not Available3
Jul 13, 2026$1,031Not Available3
Jul 14, 2026$1,206Not Available3
Jul 15, 2026$982Not Available3
Jul 16, 2026$946Available3
Jul 17, 2026$1,068Available3
Jul 18, 2026$1,120Available3
Jul 19, 2026$971Available3
Jul 20, 2026$919Available3
Jul 21, 2026$867Available3
Jul 22, 2026$930Available3
Jul 23, 2026$997Available3
Jul 24, 2026$970Available3
Jul 25, 2026$957Available3
Jul 26, 2026$945Available3
Jul 27, 2026$879Available3
Jul 28, 2026$834Available3
Jul 29, 2026$825Available3
Jul 30, 2026$858Available3
Jul 31, 2026$820Available3
Aug 1, 2026$837Available3
Aug 2, 2026$805Available3
Aug 3, 2026$793Available3
Aug 4, 2026$784Available3
Aug 5, 2026$745Available3
Aug 6, 2026$833Not Available3
Aug 7, 2026$809Not Available3
Aug 8, 2026$762Not Available3
Aug 9, 2026$755Not Available3
Aug 10, 2026$694Available3
Aug 11, 2026$736Available3
Aug 12, 2026$739Available3
Aug 13, 2026$788Available3
Aug 14, 2026$785Available3
Aug 15, 2026$790Available3
Aug 16, 2026$716Available3

Where you'll sleep

Amenities

Ocean view
Pool outdoor
Patio
Balcony
Mountain view
Wifi
Free parking
Fire extinguisher

4.9 · 9 reviews

E
Elizabeth V.
March 2026

Wonderful property! Very peaceful and relaxing. Justin was a great host!

B
Brian C.
January 2026

Really nice place to stay in St. Thomas. Beautiful view of Charlotte Amalie Harbor.

C
Courtney M.
December 2025

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, Virgin Islands (U.S.)

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 11:00 AM.
Maximum 12 guests.