St. Thomas, St. Thomas

Southwind

5 bedrooms8 beds4 baths12 guests4.9 (10)

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!
  3. 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.
  4. We provide a 24/7 maintenance and an emergency hotline.

** There are extra guest fees after 10 guests.

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!
  3. 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.
  4. We provide a 24/7 maintenance and an emergency hotline.

** There are extra guest fees after 10 guests.

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.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 16, 2026$526Available2
Jul 17, 2026$561Available2
Jul 18, 2026$732Not Available3
Jul 19, 2026$705Not Available3
Jul 20, 2026$681Not Available3
Jul 21, 2026$663Not Available3
Jul 22, 2026$747Not Available3
Jul 23, 2026$770Not Available3
Jul 24, 2026$773Available2
Jul 25, 2026$818Available2
Jul 26, 2026$824Available2
Jul 27, 2026$706Not Available3
Jul 28, 2026$665Not Available3
Jul 29, 2026$670Not Available3
Jul 30, 2026$700Not Available3
Jul 31, 2026$683Not Available3
Aug 1, 2026$684Not Available3
Aug 2, 2026$662Not Available3
Aug 3, 2026$714Not Available2
Aug 4, 2026$678Available2
Aug 5, 2026$637Available2
Aug 6, 2026$833Not Available3
Aug 7, 2026$809Not Available3
Aug 8, 2026$762Not Available3
Aug 9, 2026$755Not Available3
Aug 10, 2026$631Available3
Aug 11, 2026$628Available3
Aug 12, 2026$634Available3
Aug 13, 2026$671Available3
Aug 14, 2026$670Available3
Aug 15, 2026$653Available3
Aug 16, 2026$597Available3
Aug 17, 2026$573Available3
Aug 18, 2026$588Available3
Aug 19, 2026$605Available3
Aug 20, 2026$622Available3
Aug 21, 2026$611Available3
Aug 22, 2026$622Available3
Aug 23, 2026$556Available3
Aug 24, 2026$539Available3
Aug 25, 2026$542Available3
Aug 26, 2026$565Available3
Aug 27, 2026$629Available3
Aug 28, 2026$629Available3
Aug 29, 2026$648Available3
Aug 30, 2026$714Not Available5
Aug 31, 2026$635Not Available5
Sep 1, 2026$647Not Available5
Sep 2, 2026$686Not Available5
Sep 3, 2026$660Not Available5
Sep 4, 2026$809Not Available5
Sep 5, 2026$812Available3
Sep 6, 2026$863Available3
Sep 7, 2026$660Available3
Sep 8, 2026$630Available3
Sep 9, 2026$591Available3
Sep 10, 2026$613Available3
Sep 11, 2026$641Available3
Sep 12, 2026$627Available3
Sep 13, 2026$586Available3
Sep 14, 2026$584Available3
Sep 15, 2026$582Available3
Sep 16, 2026$618Available3
Sep 17, 2026$648Available3
Sep 18, 2026$681Available3
Sep 19, 2026$662Available3
Sep 20, 2026$675Available3
Sep 21, 2026$643Available3
Sep 22, 2026$631Available3
Sep 23, 2026$663Available3
Sep 24, 2026$675Available3
Sep 25, 2026$668Available3
Sep 26, 2026$649Available3
Sep 27, 2026$675Available3
Sep 28, 2026$641Available3
Sep 29, 2026$690Available3
Sep 30, 2026$709Available3
Oct 1, 2026$713Available3
Oct 2, 2026$698Available3
Oct 3, 2026$678Available3
Oct 4, 2026$700Available3
Oct 5, 2026$717Available3
Oct 6, 2026$773Available3
Oct 7, 2026$719Available3
Oct 8, 2026$720Available3
Oct 9, 2026$762Available3
Oct 10, 2026$814Available3
Oct 11, 2026$717Available3
Oct 12, 2026$703Available3
Oct 13, 2026$692Available3
Oct 14, 2026$705Available3

Amenities

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

4.9 · 10 reviews

M
Matt
2 weeks ago

Incredible place, just perfect. Justin and his team were responsive and incredibly helpful. 100% will stay there again!

E
Elizabeth
March 2026

Wonderful property! Very peaceful and relaxing. Justin was a great host!

B
Brian
January 2026

Really nice place to stay in St. Thomas. Beautiful view of Charlotte Amalie Harbor.

Where you'll be

St. Thomas, St. Thomas, 00802, VI

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

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.