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

4.56/10
  • 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

  • Easy cancellation


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 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 Available2
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 Available2
Feb 23, 2026$1,239Not Available3
Feb 24, 2026$1,232Not Available3
Feb 25, 2026$895Available3
Feb 26, 2026$1,023Available3
Feb 27, 2026$992Available3
Feb 28, 2026$947Available3
Mar 1, 2026$939Available3
Mar 2, 2026$886Available3
Mar 3, 2026$919Available3
Mar 4, 2026$934Available3
Mar 5, 2026$979Available3
Mar 6, 2026$1,002Available3
Mar 7, 2026$1,053Available3
Mar 8, 2026$1,030Available3
Mar 9, 2026$1,055Available3
Mar 10, 2026$1,042Available3
Mar 11, 2026$1,079Available3
Mar 12, 2026$1,121Available3
Mar 13, 2026$1,171Available3
Mar 14, 2026$1,272Available3
Mar 15, 2026$1,271Available3
Mar 16, 2026$1,279Available3
Mar 17, 2026$1,279Available3
Mar 18, 2026$1,279Available3
Mar 19, 2026$1,279Available3
Mar 20, 2026$1,279Available3
Mar 21, 2026$1,266Available3
Mar 22, 2026$1,177Available3
Mar 23, 2026$1,108Available3
Mar 24, 2026$1,129Available3
Mar 25, 2026$1,114Available3
Mar 26, 2026$1,279Available3
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$1,262Available3
Apr 6, 2026$1,279Available3
Apr 7, 2026$1,041Available3
Apr 8, 2026$1,068Available3
Apr 9, 2026$1,079Available3
Apr 10, 2026$1,072Available3
Apr 11, 2026$1,013Available3
Apr 12, 2026$954Available3
Apr 13, 2026$862Available3
Apr 14, 2026$834Available3
Apr 15, 2026$863Available3
Apr 16, 2026$943Available3
Apr 17, 2026$1,019Available3
Apr 18, 2026$1,058Available3
Apr 19, 2026$1,037Available3
Apr 20, 2026$1,093Available3
Apr 21, 2026$996Available3
Apr 22, 2026$904Available3
Apr 23, 2026$980Available3
Apr 24, 2026$1,032Available3
Apr 25, 2026$1,043Available3
Apr 26, 2026$978Available3
Apr 27, 2026$984Available3
Apr 28, 2026$1,107Available3
Apr 29, 2026$1,279Available3
Apr 30, 2026$1,240Available3
May 1, 2026$1,279Available3
May 2, 2026$1,279Available3
May 3, 2026$1,153Available3
May 4, 2026$912Available3
May 5, 2026$816Available3
May 6, 2026$799Available3
May 7, 2026$821Available3
May 8, 2026$866Available3

Top notch amenities

GUEST FAVORITES

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

Where you'll sleep



4.56 Guest love this place

10 VERIFIED REVIEWS
5.0 / 5
We loved the villa! It was clean, no bugs and you can’t beat the location. It was on the water as advertised. Both of the local restaurants had delicious food (MIMS is a little pricey, but hey, you’re on vacation). I would definitely stay there again. I have two suggestions, replace the King size bed. The frame seemed unsteady and the mattress wasn’t firm. Secondly, the tv in the living room needs a better wall mount. As soon as I discovered that one side had come out the wall, I texted Justin and I have no doubt it will be fixed for the next guest. Anyway, I LOVED OUR STAY!
S
SyntychiaStayed in January 2026
5.0 / 5
Had an amazing time Justin was a great host Very helpful and informative
A
AidenStayed in January 2026
5.0 / 5
Amazing place to stay! Clean and the host was flexible when your flight was delayed. We will be back.
W
WendyStayed in January 2026
5.0 / 5
Justin was great! Kept in touch and responded asap to any questions I had. Highly recommend!! Great location over looking Bolongo Bay
D
DawnStayed in January 2026
5.0 / 5
Everything was great! Justin also maintained communication throughout our trip just in case we needed assistance with anything.
T
TiaraStayed in January 2026
5.0 / 5
The unit was clean, and comfortable . Great view of the ocean!
K
KathiStayed in January 2026

Explore St. Thomas, St. Thomas

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

Cancellation policy

This property follows Prestige Luxury Villas’s standard cancellation policy.