$0
for 3 nights

Home in St. Thomas, VI

5 bedrooms

8 beds

4 bathrooms

12 guests

1000 sq. ft.

Operated by a Wander partner

Trusted operators, vetted by Wander

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.

Where you’ll sleep

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

Amenities

Common Amenities

  • Wifi
  • Free parking
  • Fire pit
  • Fire place
  • Outdoor dining area
  • Hike trail nearby
  • Kayaks
  • Fishing Area
  • Skiing Area
  • Massage table
  • Boat
  • Hot water
  • Carbon monoxide detector
  • Fire extinguisher
  • Smoke detector
  • First aid kit
  • Ironing board
  • Toaster
  • Dining table
  • Blackout curtains
  • Bay views
  • Pack n play
  • Ice maker
  • Mountain view
  • Luggage drop off allowed
  • Long term stays allowed
  • Bedroom door lock
  • City view
  • Paid parking
  • Private Chef
  • Butler
  • Maid
  • Blender
  • BBQ Area
  • Hot tub

Exterior

  • Wheelchair accessible
  • Patio
  • Garden
  • Ocean view

Pool

  • Outdoor pool
  • Ocean view
  • Patio

Patio

  • BBQ Utensils
  • Patio
  • Ocean view

Garden

  • Garden

Balcony

  • Balcony
  • BBQ Utensils
  • Ocean view

Living room

  • Air conditioning
  • Ceiling fan
  • TV
  • Ocean view

Kitchen

  • Kitchen
  • Dishwasher
  • Microwave
  • Oven
  • Coffee maker
  • Fridge
  • Cooking basics
  • Stove
  • Freezer
  • Dishes
  • Spices
  • Cleaning supplies

Bedroom 1

  • Hangers
  • Bed linens
  • Air conditioning
  • TV

Bedroom 2

  • Bed linens
  • Air conditioning

Bedroom 3

  • Bed linens
  • TV
  • Air conditioning

Bedroom 4

  • Safe
  • Bed linens
  • Air conditioning

Bedroom 5

  • Bed linens
  • Air conditioning

Bathroom 1

  • Hair dryer
  • Bath linens
  • Toilet
  • Shower
  • Shampoo
  • Body soap

Bathroom 2

  • Shower
  • Bath linens
  • Toilet
  • Shampoo
  • Body soap

Bathroom 3

  • Shampoo
  • Bath linens
  • Toilet
  • Shower
  • Body soap

Bathroom 4

  • Bath linens
  • Toilet
  • Shower
  • Shampoo
  • Body soap

Office

  • Dedicated workspace
  • Ocean view

Tv room

  • TV

Common area

  • Ocean view

Laundry room

  • Washer
  • Dryer
  • Iron
  • Cleaning supplies

4.9 · 10 reviews

Where you’ll be

St. Thomas, St. Thomas 00802, VI

St. Thomas, St. Thomas, VI
18.35084109-64.93022471
Timezone: America/St_Thomas

Restaurants

Sib's on the Mountain

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

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

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

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

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

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

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

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.

Sun & Sea Bar & Grill

Sun & 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

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.

Attractions

Hull Bay Beach

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.

Charlotte Amalie Overlook

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

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

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.

Drake's Seat

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.

Skyride to Paradise Point

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

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 St. Thomas

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.

Pirates Treasure Museum

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

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.

Things to know

Cancellation policy

Free cancellation up to 30 days before check-in. 50% refund up to 7 days before. No refund after that.

Property rules

Pets not allowed

No smoking - fees will apply

Events not allowed

Safety & security

Check-in after 4:00 pm

Check-out before 11:00 am

12 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Jul 28, 2026$665Not Available
Jul 29, 2026$670Not Available
Jul 30, 2026$700Not Available
Jul 31, 2026$683Not Available
Aug 1, 2026$684Not Available
Aug 2, 2026$662Not Available
Aug 3, 2026$714Not Available
Aug 4, 2026$640Available
Aug 5, 2026$658Available
Aug 6, 2026$833Not Available
Aug 7, 2026$809Not Available
Aug 8, 2026$762Not Available
Aug 9, 2026$755Not Available
Aug 10, 2026$662Available
Aug 11, 2026$575Available
Aug 12, 2026$572Available
Aug 13, 2026$600Available
Aug 14, 2026$578Available
Aug 15, 2026$590Available
Aug 16, 2026$553Available
Aug 17, 2026$534Available
Aug 18, 2026$550Available
Aug 19, 2026$571Available
Aug 20, 2026$571Available
Aug 21, 2026$577Available
Aug 22, 2026$582Available
Aug 23, 2026$534Available
Aug 24, 2026$506Available
Aug 25, 2026$494Available
Aug 26, 2026$529Available
Aug 27, 2026$597Available
Aug 28, 2026$600Available
Aug 29, 2026$630Available
Aug 30, 2026$714Not Available
Aug 31, 2026$635Not Available
Sep 1, 2026$647Not Available
Sep 2, 2026$686Not Available
Sep 3, 2026$660Not Available
Sep 4, 2026$809Not Available
Sep 5, 2026$690Available
Sep 6, 2026$753Available
Sep 7, 2026$652Available
Sep 8, 2026$642Available
Sep 9, 2026$565Available
Sep 10, 2026$583Available
Sep 11, 2026$617Available
Sep 12, 2026$630Available
Sep 13, 2026$595Available
Sep 14, 2026$570Available
Sep 15, 2026$564Available
Sep 16, 2026$591Available
Sep 17, 2026$602Available
Sep 18, 2026$642Available
Sep 19, 2026$621Available
Sep 20, 2026$631Available
Sep 21, 2026$601Available
Sep 22, 2026$591Available
Sep 23, 2026$616Available
Sep 24, 2026$635Available
Sep 25, 2026$672Available
Sep 26, 2026$656Available
Sep 27, 2026$665Available
Sep 28, 2026$629Available
Sep 29, 2026$645Available
Sep 30, 2026$681Available
Oct 1, 2026$704Available
Oct 2, 2026$692Available
Oct 3, 2026$672Available
Oct 4, 2026$677Available
Oct 5, 2026$693Available
Oct 6, 2026$694Available
Oct 7, 2026$664Available
Oct 8, 2026$716Available
Oct 9, 2026$728Available
Oct 10, 2026$804Available
Oct 11, 2026$697Available
Oct 12, 2026$680Available
Oct 13, 2026$689Available
Oct 14, 2026$718Available
Oct 15, 2026$721Available
Oct 16, 2026$710Available
Oct 17, 2026$704Available
Oct 18, 2026$766Available
Oct 19, 2026$667Available
Oct 20, 2026$703Available
Oct 21, 2026$692Available
Oct 22, 2026$719Available
Oct 23, 2026$804Available
Oct 24, 2026$803Available
Oct 25, 2026$681Available
Oct 26, 2026$680Available