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

12 guests
5 bedrooms
4 bathrooms
1000 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation

    You can cancel your trip for up to 14 days prior to start.


About this 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)
Feb 6, 2026$1,279Not Available3
Feb 7, 2026$1,279Not Available3
Feb 8, 2026$1,279Not Available3
Feb 9, 2026$1,279Not Available3
Feb 10, 2026$1,279Not Available3
Feb 11, 2026$1,279Not Available3
Feb 12, 2026$1,279Not Available3
Feb 13, 2026$1,279Not Available3
Feb 14, 2026$1,279Not Available5
Feb 15, 2026$1,279Not Available3
Feb 16, 2026$1,279Not Available3
Feb 17, 2026$1,279Not Available3
Feb 18, 2026$1,279Not Available3
Feb 19, 2026$1,279Not Available3
Feb 20, 2026$1,279Not Available3
Feb 21, 2026$1,279Not Available3
Feb 22, 2026$1,250Not Available3
Feb 23, 2026$1,239Not Available3
Feb 24, 2026$1,232Not Available3
Feb 25, 2026$878Available3
Feb 26, 2026$980Available3
Feb 27, 2026$958Available3
Feb 28, 2026$907Available3
Mar 1, 2026$915Available3
Mar 2, 2026$851Available3
Mar 3, 2026$876Available3
Mar 4, 2026$927Available3
Mar 5, 2026$984Available3
Mar 6, 2026$1,039Available3
Mar 7, 2026$1,081Available3
Mar 8, 2026$1,154Available3
Mar 9, 2026$1,181Available3
Mar 10, 2026$1,140Available3
Mar 11, 2026$1,215Available3
Mar 12, 2026$1,184Available3
Mar 13, 2026$1,252Available3
Mar 14, 2026$1,279Available3
Mar 15, 2026$1,279Available3
Mar 16, 2026$1,279Not Available3
Mar 17, 2026$1,279Not Available3
Mar 18, 2026$1,279Not Available3
Mar 19, 2026$1,279Not Available3
Mar 20, 2026$1,279Not Available3
Mar 21, 2026$1,266Not Available3
Mar 22, 2026$1,177Not Available3
Mar 23, 2026$1,228Available2
Mar 24, 2026$1,279Available2
Mar 25, 2026$1,261Available2
Mar 26, 2026$1,279Not Available3
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$1,279Available3
Apr 6, 2026$1,279Available3
Apr 7, 2026$1,064Available3
Apr 8, 2026$1,097Available3
Apr 9, 2026$1,144Available3
Apr 10, 2026$1,125Available3
Apr 11, 2026$1,069Available3
Apr 12, 2026$985Available3
Apr 13, 2026$894Available3
Apr 14, 2026$871Available3
Apr 15, 2026$896Available3
Apr 16, 2026$976Available3
Apr 17, 2026$1,048Available3
Apr 18, 2026$1,073Available3
Apr 19, 2026$1,047Available3
Apr 20, 2026$1,102Available3
Apr 21, 2026$927Available3
Apr 22, 2026$912Available3
Apr 23, 2026$985Available3
Apr 24, 2026$1,065Available3
Apr 25, 2026$1,056Available3
Apr 26, 2026$995Available3
Apr 27, 2026$1,001Available3
Apr 28, 2026$1,121Available3
Apr 29, 2026$1,279Available3
Apr 30, 2026$1,279Available3
May 1, 2026$1,279Available3
May 2, 2026$1,279Available3
May 3, 2026$1,229Available3
May 4, 2026$936Available3
May 5, 2026$839Available3
May 6, 2026$837Available3
May 7, 2026$853Available3

Amenities

Patio
Balcony
Wifi
Free parking
Hot water
Carbon monoxide detector
Smoke detector
First aid kit
Air conditioning

Where you'll sleep



Explore St. Thomas, St. Thomas

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 10:00 AM
12 guests maximum
Pets not allowed
Events require approval

Cancellation policy

This property follows Tom Fallenstein St Thomas’s standard cancellation policy.