St. Thomas, St. Thomas

Southwind

5 bedrooms 8 beds 4 baths 12 guests New

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$522Available2
May 19, 2026$550Available2
May 20, 2026$606Available2
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$648Not Available3
Jun 3, 2026$648Available3
Jun 4, 2026$926Not Available3
Jun 5, 2026$897Not Available3
Jun 6, 2026$904Not Available3
Jun 7, 2026$878Not Available3
Jun 8, 2026$696Available3
Jun 9, 2026$704Available3
Jun 10, 2026$703Available3
Jun 11, 2026$727Available3
Jun 12, 2026$716Available3
Jun 13, 2026$743Available3
Jun 14, 2026$760Available3
Jun 15, 2026$850Available3
Jun 16, 2026$798Available3
Jun 17, 2026$830Available3
Jun 18, 2026$828Available3
Jun 19, 2026$896Available3
Jun 20, 2026$852Available3
Jun 21, 2026$830Available3
Jun 22, 2026$836Available3
Jun 23, 2026$896Available3
Jun 24, 2026$1,029Available3
Jun 25, 2026$1,069Available3
Jun 26, 2026$1,160Available3
Jun 27, 2026$913Available3
Jun 28, 2026$993Available3
Jun 29, 2026$822Available3
Jun 30, 2026$818Available3
Jul 1, 2026$772Available3
Jul 2, 2026$953Available3
Jul 3, 2026$973Available3
Jul 4, 2026$959Available3
Jul 5, 2026$851Available3
Jul 6, 2026$868Available3
Jul 7, 2026$852Available3
Jul 8, 2026$891Available3
Jul 9, 2026$990Available3
Jul 10, 2026$855Available3
Jul 11, 2026$956Not Available3
Jul 12, 2026$1,132Not Available3
Jul 13, 2026$930Not Available3
Jul 14, 2026$1,095Not Available3
Jul 15, 2026$909Not Available3
Jul 16, 2026$852Available3
Jul 17, 2026$1,063Available3
Jul 18, 2026$1,236Available3
Jul 19, 2026$919Available3
Jul 20, 2026$884Available3
Jul 21, 2026$836Available3
Jul 22, 2026$866Available3
Jul 23, 2026$957Available3
Jul 24, 2026$942Available3
Jul 25, 2026$931Available3
Jul 26, 2026$934Available3
Jul 27, 2026$851Available3
Jul 28, 2026$808Available3
Jul 29, 2026$807Available3
Jul 30, 2026$851Available3
Jul 31, 2026$827Available3
Aug 1, 2026$829Available3
Aug 2, 2026$800Available3
Aug 3, 2026$782Available3
Aug 4, 2026$778Available3
Aug 5, 2026$728Available3
Aug 6, 2026$833Not Available3
Aug 7, 2026$809Not Available3
Aug 8, 2026$762Not Available3
Aug 9, 2026$755Not Available3
Aug 10, 2026$667Available3
Aug 11, 2026$709Available3
Aug 12, 2026$712Available3
Aug 13, 2026$767Available3
Aug 14, 2026$757Available3
Aug 15, 2026$760Available3
Aug 16, 2026$701Available3

Where you'll sleep

Amenities

Ocean view
Pool outdoor
Patio
Balcony
Mountain view
Free parking
Washer
Carbon monoxide detector

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Where you'll be

St. Thomas, St. Thomas, 00802, VI

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.