Operated by a Wander partner
Trusted operators, vetted by Wander
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?
** 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.
Bedroom 1
2 king beds
Bedroom 2
1 queen bed, 1 twin trundle bed
Bedroom 3
2 twin bunk beds
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Bedroom 1
2 king beds
Bedroom 2
1 queen bed, 1 twin trundle bed
Bedroom 3
2 twin bunk beds
Bedroom 4
1 king bed
Bedroom 5
1 king bed
St. Thomas, St. Thomas 00802, VI
St. Thomas, St. Thomas, VISun & Sea Bar & Grill offers fresh, locally sourced seafood and craft drinks in a relaxed waterfront setting where you can enjoy stunning ocean views and live local music. Its family-friendly vibe and unique fresh catch cooking service make it a perfect spot for a memorable meal by the sea.
Yacht Haven Grande offers a vibrant dining scene with a mix of sophisticated Caribbean flavors and casual waterfront eateries, all set against the stunning backdrop of a luxury marina. Guests enjoy fresh, locally inspired cuisine in stylish, inviting atmospheres perfect for both relaxed and elegant meals.
Sib's on the Mountain offers a relaxed, family-friendly atmosphere with stunning mountain views, serving flavorful comfort food like grilled ahi tuna and ribs, all in a historic setting that’s been a local favorite since 1924. The welcoming vibe makes it a perfect spot to unwind and connect.
Northside Grind is a vibrant Caribbean coffee shop and deli in St. Thomas, known for its fresh breakfast sandwiches, signature coffee blends, and tropical smoothies, all served with friendly, welcoming service in a relaxed island atmosphere.
Bolongo Bay Beach Resort’s Iggies' Oasis offers vibrant Caribbean-inspired cuisine in a lively, three-story open-air setting with stunning ocean views, poolside dining, handcrafted cocktails, and live island music for an unforgettable tropical experience.
The Greenhouse Restaurant & Bar in Charlotte Amalie offers a vibrant blend of American and Caribbean flavors in a relaxed waterfront setting, perfect for enjoying fresh seafood and lively island vibes. Its casual ambiance invites guests to savor local tastes with a scenic view.
Oceana Restaurant & Bistro in St. Thomas offers a refined dining experience with fresh, locally sourced seafood and expertly crafted dishes, all set against stunning Caribbean sea views in a relaxed yet elegant ambiance.
Gladys' Café offers authentic Caribbean flavors like curry goat and stewed oxtails in a warm, casual setting filled with local charm and homemade hot sauces that spice up every dish. This longtime St. Thomas favorite blends hearty comfort food with a welcoming, down-home atmosphere.
The Smoking Rooster offers expertly smoked BBQ meats with house-made rubs and sauces, paired perfectly with a diverse rum selection. Enjoy a relaxed, rustic garden or lively indoor bar atmosphere just steps from the St. Thomas cruise port.
Prime at Paradise Point offers an exceptional steakhouse experience with prime cuts, fresh local seafood, and handcrafted cocktails, all set against breathtaking panoramic views of the Caribbean and a romantic, intimate ambiance.
Drake's Seat offers breathtaking panoramic views of Magens Bay and the Virgin Islands, blending rich pirate lore with stunning Caribbean scenery. It's perfect for history buffs, photographers, and anyone seeking a peaceful spot to soak in unforgettable sunsets.
The Skyride to Paradise Point offers a thrilling 7-minute cable car ride 700 feet above St. Thomas, delivering stunning panoramic views of the harbor, cruise ships, and nearby islands—perfect for travelers seeking breathtaking scenery and a relaxing escape with dining and drinks at the summit.
Coral World Ocean Park offers unforgettable marine encounters like walking underwater with a Sea Trek helmet, swimming with dolphins, and exploring an underwater observatory. It’s perfect for families and anyone eager to connect closely with vibrant Caribbean sea life.
Tree Limin' Extreme Zipline in St. Thomas offers an exhilarating adventure through lush rainforest canopies with breathtaking island views, perfect for thrill-seekers and nature lovers alike. Friendly, expert guides ensure a safe and unforgettable experience for both first-timers and seasoned zipliners.
The Pirates Treasure Museum offers an immersive adventure with interactive exhibits and authentic pirate artifacts, perfect for history buffs, families, and anyone fascinated by pirate legends and deep-sea shipwrecks. Climb aboard and experience the thrill of the Golden Age of Piracy firsthand.
Bolongo Bay Beach Resort offers a vibrant Caribbean escape with stunning ocean views, lively live music, and unique water activities like snorkeling, paddleboarding, and the famous Snorkel Booze Hunt. It’s perfect for adventure seekers, families, and anyone craving a laid-back island vibe.
Hull Bay Beach offers a peaceful escape with crystal-clear waters perfect for snorkeling among sea turtles, stingrays, and colorful fish. Ideal for nature lovers and those seeking a relaxed vibe away from crowded tourist spots.
Experience breathtaking panoramic views of Charlotte Amalie's sparkling harbor, nearby islands, and the Caribbean Sea from this scenic overlook—perfect for photographers, sunset lovers, and anyone seeking stunning photo opportunities without strenuous hiking.
Fort Christian is a captivating 17th-century Danish fort in Charlotte Amalie, offering history lovers a glimpse into colonial life, military defense, and island governance. It’s perfect for those fascinated by architecture, Caribbean history, and cultural heritage.
Phantasea Tropical Botanical Garden is a vibrant island oasis where visitors can explore over 1,000 orchids, exotic tropical plants, and charming wildlife while enjoying stunning panoramic views of Magens Bay and nearby islands. It’s perfect for nature lovers, families, and anyone seeking a peaceful, colorful escape.
Free cancellation up to 14 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 11:00 am
12 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 21, 2026 | $663 | Not Available |
| Jul 22, 2026 | $747 | Not Available |
| Jul 23, 2026 | $770 | Not Available |
| Jul 24, 2026 | $665 | Available |
| Jul 25, 2026 | $693 | Available |
| Jul 26, 2026 | $696 | Available |
| Jul 27, 2026 | $706 | Not Available |
| Jul 28, 2026 | $665 | Not Available |
| Jul 29, 2026 | $670 | Not Available |
| Jul 30, 2026 | $700 | Not Available |
| Jul 31, 2026 | $683 | Not Available |
| Aug 1, 2026 | $684 | Not Available |
| Aug 2, 2026 | $662 | Not Available |
| Aug 3, 2026 | $714 | Not Available |
| Aug 4, 2026 | $594 | Available |
| Aug 5, 2026 | $605 | Available |
| Aug 6, 2026 | $833 | Not Available |
| Aug 7, 2026 | $809 | Not Available |
| Aug 8, 2026 | $762 | Not Available |
| Aug 9, 2026 | $755 | Not Available |
| Aug 10, 2026 | $584 | Available |
| Aug 11, 2026 | $580 | Available |
| Aug 12, 2026 | $586 | Available |
| Aug 13, 2026 | $620 | Available |
| Aug 14, 2026 | $625 | Available |
| Aug 15, 2026 | $625 | Available |
| Aug 16, 2026 | $589 | Available |
| Aug 17, 2026 | $562 | Available |
| Aug 18, 2026 | $578 | Available |
| Aug 19, 2026 | $606 | Available |
| Aug 20, 2026 | $614 | Available |
| Aug 21, 2026 | $601 | Available |
| Aug 22, 2026 | $609 | Available |
| Aug 23, 2026 | $542 | Available |
| Aug 24, 2026 | $519 | Available |
| Aug 25, 2026 | $512 | Available |
| Aug 26, 2026 | $538 | Available |
| Aug 27, 2026 | $611 | Available |
| Aug 28, 2026 | $615 | Available |
| Aug 29, 2026 | $639 | Available |
| Aug 30, 2026 | $714 | Not Available |
| Aug 31, 2026 | $635 | Not Available |
| Sep 1, 2026 | $647 | Not Available |
| Sep 2, 2026 | $686 | Not Available |
| Sep 3, 2026 | $660 | Not Available |
| Sep 4, 2026 | $809 | Not Available |
| Sep 5, 2026 | $743 | Available |
| Sep 6, 2026 | $800 | Available |
| Sep 7, 2026 | $678 | Available |
| Sep 8, 2026 | $637 | Available |
| Sep 9, 2026 | $587 | Available |
| Sep 10, 2026 | $605 | Available |
| Sep 11, 2026 | $634 | Available |
| Sep 12, 2026 | $623 | Available |
| Sep 13, 2026 | $582 | Available |
| Sep 14, 2026 | $556 | Available |
| Sep 15, 2026 | $558 | Available |
| Sep 16, 2026 | $582 | Available |
| Sep 17, 2026 | $608 | Available |
| Sep 18, 2026 | $675 | Available |
| Sep 19, 2026 | $657 | Available |
| Sep 20, 2026 | $671 | Available |
| Sep 21, 2026 | $638 | Available |
| Sep 22, 2026 | $628 | Available |
| Sep 23, 2026 | $658 | Available |
| Sep 24, 2026 | $679 | Available |
| Sep 25, 2026 | $677 | Available |
| Sep 26, 2026 | $658 | Available |
| Sep 27, 2026 | $677 | Available |
| Sep 28, 2026 | $635 | Available |
| Sep 29, 2026 | $646 | Available |
| Sep 30, 2026 | $687 | Available |
| Oct 1, 2026 | $690 | Available |
| Oct 2, 2026 | $689 | Available |
| Oct 3, 2026 | $671 | Available |
| Oct 4, 2026 | $682 | Available |
| Oct 5, 2026 | $704 | Available |
| Oct 6, 2026 | $731 | Available |
| Oct 7, 2026 | $679 | Available |
| Oct 8, 2026 | $716 | Available |
| Oct 9, 2026 | $749 | Available |
| Oct 10, 2026 | $830 | Available |
| Oct 11, 2026 | $708 | Available |
| Oct 12, 2026 | $703 | Available |
| Oct 13, 2026 | $709 | Available |
| Oct 14, 2026 | $717 | Available |
| Oct 15, 2026 | $728 | Available |
| Oct 16, 2026 | $709 | Available |
| Oct 17, 2026 | $698 | Available |
| Oct 18, 2026 | $731 | Available |
| Oct 19, 2026 | $653 | Available |