St. Thomas, St. Thomas

Southwind

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12 guests
5 bedrooms
4 bathrooms
1000 sqft

Southwind Villa: A Classic West Indies Retreat with Timeless Soul

  • Ocean view
  • Hot tub
  • Fire pit
12 guests
5 bedrooms
4 bathrooms
1000 sqft
  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 11:00 AM

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

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Mar 27, 2026$1,279Not Available3
Mar 28, 2026$1,279Not Available3
Mar 29, 2026$1,279Not Available3
Mar 30, 2026$1,279Not Available3
Mar 31, 2026$1,279Not Available3
Apr 1, 2026$1,279Not Available3
Apr 2, 2026$1,279Not Available3
Apr 3, 2026$1,279Not Available3
Apr 4, 2026$1,279Not Available3
Apr 5, 2026$1,051Not Available3
Apr 6, 2026$857Not Available3
Apr 7, 2026$822Not Available3
Apr 8, 2026$800Not Available3
Apr 9, 2026$865Not Available3
Apr 10, 2026$898Not Available3
Apr 11, 2026$889Not Available3
Apr 12, 2026$755Available3
Apr 13, 2026$717Available3
Apr 14, 2026$691Available3
Apr 15, 2026$701Available3
Apr 16, 2026$747Available3
Apr 17, 2026$780Available3
Apr 18, 2026$810Available3
Apr 19, 2026$820Available3
Apr 20, 2026$825Available3
Apr 21, 2026$767Available3
Apr 22, 2026$766Available3
Apr 23, 2026$926Not Available3
Apr 24, 2026$963Not Available3
Apr 25, 2026$945Not Available3
Apr 26, 2026$890Not Available3
Apr 27, 2026$934Not Available3
Apr 28, 2026$867Available3
Apr 29, 2026$983Available3
Apr 30, 2026$988Available3
May 1, 2026$988Available3
May 2, 2026$987Available3
May 3, 2026$878Available3
May 4, 2026$737Available3
May 5, 2026$684Available3
May 6, 2026$688Available3
May 7, 2026$733Available3
May 8, 2026$789Available3
May 9, 2026$772Available3
May 10, 2026$740Available3
May 11, 2026$701Available3
May 12, 2026$687Available3
May 13, 2026$823Available3
May 14, 2026$871Available3
May 15, 2026$912Available3
May 16, 2026$829Available3
May 17, 2026$777Available3
May 18, 2026$709Available3
May 19, 2026$691Available3
May 20, 2026$805Available3
May 21, 2026$859Available3
May 22, 2026$934Available3
May 23, 2026$1,018Available3
May 24, 2026$1,018Available3
May 25, 2026$1,018Available3
May 26, 2026$921Available3
May 27, 2026$809Available3
May 28, 2026$873Available3
May 29, 2026$870Available3
May 30, 2026$897Available3
May 31, 2026$868Available3
Jun 1, 2026$845Available3
Jun 2, 2026$869Available3
Jun 3, 2026$817Available3
Jun 4, 2026$932Available3
Jun 5, 2026$887Available3
Jun 6, 2026$881Available3
Jun 7, 2026$842Available3
Jun 8, 2026$891Available3
Jun 9, 2026$849Available3
Jun 10, 2026$927Available3
Jun 11, 2026$904Available3
Jun 12, 2026$909Available3
Jun 13, 2026$1,086Available3
Jun 14, 2026$997Available3
Jun 15, 2026$843Available3
Jun 16, 2026$854Available3
Jun 17, 2026$917Available3
Jun 18, 2026$957Available3
Jun 19, 2026$1,129Available3
Jun 20, 2026$1,049Available3
Jun 21, 2026$1,122Available3
Jun 22, 2026$979Available3
Jun 23, 2026$1,128Available3
Jun 24, 2026$1,261Available3
Jun 25, 2026$1,238Available3

Where you'll sleep

Amenities

GUEST FAVORITES

Ocean view
Hot tub
Fire pit
Fire place
BBQ Area
Patio
Balcony
Outdoor dining area
Air conditioning

Where you'll be

Immerse yourself in the captivating beauty of St. Thomas, where iconic panoramic views are just steps away. Take in breathtaking vistas from Drake's Seat and the Charlotte Amalie Overlook, before exploring the rich history of nearby Bluebeard's Castle. For vibrant island experiences, a short walk brings you to Yacht Haven Grande's shops and dining, or grab a coffee at Northside Grind, offering the perfect blend of serene escape and lively adventure.

Things to know

Here are some things which you should know before booking Southwind

House rules

Check-in after 4:00 PM
Check-out before 11:00 AM
12 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval