St. Thomas, St. Thomas

Southwind

Click to copy
12 guests
5 bedrooms
4 bathrooms
1000 sqft

Southwind Villa: A Classic West Indies Retreat with Timeless Soul

4.9
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$756Available3
Apr 13, 2026$721Available3
Apr 14, 2026$695Available3
Apr 15, 2026$705Available3
Apr 16, 2026$750Available3
Apr 17, 2026$795Available3
Apr 18, 2026$819Available3
Apr 19, 2026$836Available3
Apr 20, 2026$839Available3
Apr 21, 2026$771Available3
Apr 22, 2026$771Available2
Apr 23, 2026$926Not Available2
Apr 24, 2026$963Not Available3
Apr 25, 2026$945Not Available3
Apr 26, 2026$890Not Available3
Apr 27, 2026$934Not Available3
Apr 28, 2026$898Available3
Apr 29, 2026$1,032Available3
Apr 30, 2026$1,035Available3
May 1, 2026$1,036Available3
May 2, 2026$1,027Available3
May 3, 2026$907Available3
May 4, 2026$747Available3
May 5, 2026$698Available3
May 6, 2026$701Available3
May 7, 2026$738Available3
May 8, 2026$800Available3
May 9, 2026$779Available3
May 10, 2026$745Available3
May 11, 2026$706Available3
May 12, 2026$692Available3
May 13, 2026$823Available3
May 14, 2026$872Available3
May 15, 2026$914Available3
May 16, 2026$836Available3
May 17, 2026$783Available3
May 18, 2026$716Available3
May 19, 2026$704Available3
May 20, 2026$832Available3
May 21, 2026$869Available3
May 22, 2026$967Available3
May 23, 2026$1,084Available3
May 24, 2026$1,143Available3
May 25, 2026$1,115Available3
May 26, 2026$966Available3
May 27, 2026$815Available3
May 28, 2026$873Available3
May 29, 2026$878Available3
May 30, 2026$901Available3
May 31, 2026$874Available3
Jun 1, 2026$902Available3
Jun 2, 2026$902Available3
Jun 3, 2026$838Available3
Jun 4, 2026$987Available3
Jun 5, 2026$914Available3
Jun 6, 2026$897Available3
Jun 7, 2026$845Available3
Jun 8, 2026$845Available3
Jun 9, 2026$845Available3
Jun 10, 2026$921Available3
Jun 11, 2026$904Available3
Jun 12, 2026$899Available3
Jun 13, 2026$1,085Available3
Jun 14, 2026$1,072Available3
Jun 15, 2026$849Available3
Jun 16, 2026$851Available3
Jun 17, 2026$846Available3
Jun 18, 2026$957Available3
Jun 19, 2026$1,090Available3
Jun 20, 2026$1,056Available3
Jun 21, 2026$1,094Available3
Jun 22, 2026$999Available3
Jun 23, 2026$1,174Available3
Jun 24, 2026$1,204Available3
Jun 25, 2026$1,232Available3

Where you'll sleep

Amenities

Patio
Balcony
Wifi
Free parking
Hot water
Fire extinguisher
Carbon monoxide detector
Smoke detector
First aid kit

4.9 Guest love this place

9 VERIFIED REVIEWS
5.0 / 5
Wonderful property! Very peaceful and relaxing. Justin was a great host!
E
ElizabethStayed in March 2026
5.0 / 5
Really nice place to stay in St. Thomas. Beautiful view of Charlotte Amalie Harbor.
B
BrianStayed in January 2026
5.0 / 5
The pictures do NOT do that view justice. Insanely beautiful and the most friendly and helpful hosts. would book again 100 times over
C
CourtneyStayed in December 2025

Where you'll be

Experience the unparalleled beauty of St. Thomas from a commanding position, with panoramic island views just steps away at Drake's Seat and the Charlotte Amalie Overlook. A short walk unveils the historical charm of Bluebeard's Castle, while nearby, guests can explore the bustling Yacht Haven Grande, home to diverse shopping, dining, and convenient stops like Northside Grind and Moe's Fresh Market, all within easy reach for an unforgettable island retreat.

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