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Classic West Indies Retreat with Timeless Soul

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Pool
Property grounds
Property grounds
Fridge, microwave, oven, stovetop
Interior

Reviews

9.6 out of 10
Exceptional

Entire home

5 bedrooms4 bathrooms

Popular amenities

  • Parking available
  • Breakfast available
  • Dryer
  • Pool
  • Washer
  • Barbecue grill

Explore the area

Map
St. Thomas, St. Thomas
  • Blackbeard's Castle
    ‪14 min walk‬
  • 99 Steps
    ‪17 min walk‬
  • Magens Bay Beach
    ‪5 min drive‬
  • St. Thomas (STT-Cyril E. King)
    ‪9 min drive‬

Room options

About the neighborhood

Charlotte Amalie

Seaside stay .Within 2 miles (3 km) of this St. Thomas vacation home, you'll find Drake's Seat and Blackbeard's Castle. St. Thomas Synagogue and Frenchtown are also within 2 miles (3 km).

What's nearby

  • Blackbeard's Castle - 14 min walk - 0.8 miles
  • 99 Steps - 17 min walk - 0.9 miles
  • Yacht Haven Grande Marina - 4 min drive - 2.1 miles
  • Magens Bay Beach - 5 min drive - 2.7 miles
  • Magens Bay - 7 min drive - 2.9 miles

Getting around

  • Cyril E. King Airport (STT) - 20 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Green House Bar & Restaurant - ‬4 min drive
  • ‪Magen's Bay Beach Bar & Cafe - ‬8 min drive
  • ‪Carnival Village - ‬5 min drive
  • ‪Virgilio's - ‬4 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Classic West Indies Retreat with Timeless Soul

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.**
Guests will be required to sign a rental agreement and may also be required to add a credit card for incidentals. If you'd like more information, please just ask and we'll be happy to explain. A damage deposit "authorization hold" will be placed 24 hours before arrival and released within 7 days of departure.

1. No parties or events
2. No smoking
3. Respect your neighbors
4. Enjoy!

Property manager

Justin Thomas

Languages

English

Similar properties

Property amenities

Ski

  • Close to skiing

Pool/Spa

  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car recommended
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Breakfast available for a fee
  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Stair-free path to entrance
  • Tile flooring in public areas
  • Well-lit path to entrance
  • Wheelchair accessibility

Services and conveniences

  • Change of bedsheets (on request)
  • Iron/ironing board
  • Meal delivery service

Location highlights

  • In the mountains
  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Whale watching nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 80% lighting from LEDs
  • Bed sheets changed on request
  • Garden
  • Locally-owned and organized tours and activities
  • Vegan dining options
  • Water-efficient showers
  • Water-efficient toilets

Policies

Check-in

Contactless check-in available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Children and extra beds

  • Children are welcome.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

381829

Frequently asked questions

How close is Classic West Indies Retreat with Timeless Soul to the airport?

This vacation home is 1.8 mi (9-min drive) away from the St. Thomas (SPB-St. Thomas Seaplane Base) airport, the closest popular airport to the property.

Does Classic West Indies Retreat with Timeless Soul have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Classic West Indies Retreat with Timeless Soul to the beach?

This vacation home is 7.2 mi (26-min drive) from Sapphire Beach and 17.6 mi (72-min drive) from Trunk Bay. Don't forget your sunscreen!

Does Classic West Indies Retreat with Timeless Soul offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Classic West Indies Retreat with Timeless Soul?

No, there is no casino at this vacation home.

Is there free parking at Classic West Indies Retreat with Timeless Soul?

Free parking is not available at this vacation home.

Does Classic West Indies Retreat with Timeless Soul have a pool?

Yes, there's a private pool.

Does Classic West Indies Retreat with Timeless Soul have a spa?

There are no spa services available at this vacation home.

How close is Classic West Indies Retreat with Timeless Soul to downtown St. Thomas?

This vacation home is 0.1 mi away from Mafolie.

Classic West Indies Retreat with Timeless Soul Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 35 out of 43 reviews
Rating 8 - Good. 5 out of 43 reviews
Rating 6 - Okay. 2 out of 43 reviews
Rating 4 - Poor. 1 out of 43 reviews
Rating 2 - Terrible. 0 out of 43 reviews

9.4/10

Cleanliness

Reviews

10/10 Excellent

Pamela C.

Liked: Cleanliness

Well appointed villa great for extended family

Wonderful stay at Southwind Villa with a large family group. The bedroom set up gave lots of privacy. Large pool which everyone loved. Centralized location in Mafolie Estate convenient to beaches and town. Villa is well appointed with everything needed. Stunning views of the harbor. Our family group had a wonderful vacation!
Stayed 5 nights in Feb 2025

10/10 Excellent

James Y.

Liked: Cleanliness

Lissette manor

Amazing!! Loved the house and location.
Stayed 8 nights in Dec 2024

10/10 Excellent

Sarah M.

Liked: Cleanliness

St.Thomas Get Away

We enjoyed our stay, we loved the pool, balconies and of course the view. Property management was always available too if needed! we will be back
Stayed 7 nights in Jul 2024

8/10 Good

Carol D.

Liked: Cleanliness

Family Reunion

We had a wonderful time at Southwind Villa. The location is great, the views are spectacular and the pool is fabulous. The house is sprawling and spacious, so our group of 8 had lots of room to spread out. We spent a lot of time on the covered open-air veranda/porch, which was great during the heat of the day. We did need to call the property managers regarding a few items, but the issues were addressed within a reasonable time. Overall, this place is quite lovely and comfortable .... I really hated to leave.
Stayed 7 nights in Jun 2024

8/10 Good

Kenneth F.

Liked: Cleanliness

Great View

Great view with lots of living space... This place is great for groups of friends or large families. Everyone has their own space with extra living rooms, private baths and just extra space. The house and grounds just need a little TLC and this place would be a great 5 star. We had some light bulb issue not working around the pool, in the pool and around the grounds outside the house. The kitchen and dining area was great for those group stay home cookouts. Overall our group had a great stay and would stay there again in the future. Did I say the view was GREAT!!!!
Stayed 7 nights in Feb 2024

6/10 Okay

Frank D.

Liked: Cleanliness

Needs some TLC

This property is in a great location with spectacular views. It was very clean and we enjoyed our stay for the most part. The property is showing it’s age and is in need of some updates and maintenance. Some of the issues we encountered: refrigerator wasn’t as cold a it should be and needed a service call. Ice maker didn’t work. Water sputtered and splashed out of the faucets and occasionally had a brown tint. The house was supplied with a water cooler however, there was only 1 spare bottle and half in the cooler. Our group of 7 quickly depleted this and despite repeated requests to the property manager and multiple promises to restock, we never received it and had to buy our own drinking water. Of the 6 lounges around the pool, only 2 had cushions and both were stained and ripped. 2 of the toilets ran constantly and were reported but not repaired. Multiple signs around the house requested water conservation and repairing the toilets would be a great place to start. Again we enjoyed our stay but these issues, especially the lack of drinking water was detracted from the enjoyment of the property.
Stayed 7 nights in Jun 2023

10/10 Excellent

Thomie T.

Liked: Cleanliness

Great family home!

Wonderful, clean, bright space for our family vacation. The pool was fantastic, the view was amazing and Sibs was so much fun! Jerscillia was very helpful and facilitated a smooth check in and great stay.!
Stayed 5 nights in Dec 2022

10/10 Excellent

Jerrod V.

Liked: Cleanliness

Family (of 6) Summer Vacation

Our family of 6 (2 adults, 4 kids ages 3, 6, 9, 11) stayed at the Southwind Villa from June 20-24 and had a wonderful time! The house is quite large - when we come back, we'll be sure to bring additional friends / family. The house / location was as described. It had a beautiful view of the harbor and we were able to enjoy several breakfasts / dinners (and late night drinks) watching the cruise ships come in, etc. There is a wireless speaker system that allowed us to listen to music as well - a welcome surprise. The pool was spacious and overall, the house was clean. It was well-stocked with things like olive oil, etc., which we could have forgone when we went grocery shopping. The house is multiple levels, so if you have kids, just know that they might stay in different parts of the house. That said, there was enough room in the master suite and main house for our full family. The bedrooms have air conditioners that work very well and kept us cool, despite the warm temperatures. And the beach umbrella / chairs and ice chest came in very handy! The welcome guide that Pat and Sally provided was full of great information and tips - we used it extensively during our trip, including restaurant recommendations, beaches to see, etc. And their short history of the island / area was excellent! Jerscillia - the onsite property manager - was excellent. She met us at the house, gave us an overview and was generally available with questions via text / phone. The only challenge was finding the location - fortunately Jerscillia sent us directions via Apple maps (we had a rental car - a must to get around see the island). Our Google Maps didn't work as well, but once we pinned the location, it was easy getting around. We would highly recommend Southwind Villa for the reasons above. My greatest memory - in addition to hearing our children's fun / laughter at the pool - was the wonderful view of the island from above. You won't regret staying here! The Vaughans (Dallas, TX)
Stayed 4 nights in Jun 2022

10/10 Excellent

James K.

Liked: Cleanliness

All good

Great place to relax and decompress especially during these difficult travel times. All as advertised and great base location for seeing St Thomas. Thanks Pat and Sally.
Stayed 6 nights in Jun 2022

10/10 Excellent

Brittani M.

Liked: Cleanliness

1000% recommend

The Good: 1. We could stay here all over again, and again, and again. We spent half our time in this vrbo and the other half the time in margaritaville. Everyone wishes we had more time at this vrbo. 2. Communication was amazing. Pat answered my messages within minutes. There is also a property manager who walks you around the facility when you arrive and gives you information and helpful tips about the facility. It was definitely helpful. 3. It has THE best views of the whole island. The view of this vrbo was like looking at a postcard or a hand painting. It was unbelievable. 4. House was very clean, and everything we needed was there. 5. There is a little restaurant/bar, called Sibs, within walking distance of the vrbo with some of the best food and drinks we had during our whole stay. (They also have iced coffee) 6. Location was nice. It didn't take us too long to get anywhere on the island. 7. The pool was HUGE! We had so much fun. The pictures don't even do it justice. 8. The layout of the whole vrbo was exactly what we needed. All the rooms are separated on the property so everyone had their own privacy. 9. The owner will send you a very helpful booklet for your stay. It helps you to choose good excursions and the best places to buy food and stuff. 10. The Air-conditioning worked very well. As long as you keep the doors shut it will get very cool in your room. The bad: We had a noise complaint. It's in the rules and not the owners fault. He was very understanding when he got the call. Just be careful because they will call the owner even before the 9pm "quiet time". Definitely not a deal breaker, because we would do it all over again. And next time we come to st thomas we will be looking into staying here again, we will just watch out noise level a little better.
Stayed 4 nights in Jun 2022

10/10 Excellent

Ambika S.

Liked: Cleanliness

Exceptional stay

We had a wonderful time at Southwind Villa. We were a multi generational family with young children and the Villa had everything we needed to have a restful stay in St. Thomas. Pat was super accessible ahead of time and answered all our questions. The property manager was also so sweet and accommodating. The pictures of this place don’t do it justice. We were in awe of the views from every angle of the villa. Do yourself a favor and book this place. You won’t be disappointed.
Stayed 4 nights in May 2022

10/10 Excellent

Jason B.

Liked: Cleanliness

Beautiful Views and Attentive Owner/Property Manager

Upon Booking, Pat and Sally send you a large welcome guide (~35 pages) with everything you need to know about your vacation. Upon arriving you are given a tour of the property by the property manager, and if anything comes up she acts quickly and promptly to make sure your stay is great!
Stayed 7 nights in May 2022

4/10 Poor

Sheila & Norm B.

Disliked: Cleanliness

overall impression

Not as clean as reviews stated. The pool wasn't clean . There was a lot of visible dust over doorways and mirrors . The floors were not clean and there was mold starting on bathroom ceilings. We also had a situation where some bathrooms had no toilet paper some had a 1/4 of a roll and no extra rolls anywhere . We called the manager early our first morning to ask for toilet paper and she didn't come with it until 7:00 PM . Otherwise the view was great .
Stayed 3 nights in May 2022

10/10 Excellent

Stephanie R.

Liked: Cleanliness

Trip of a lifetime

My family and I came to the Southwind villa for spring break. We had an amazing time. Everything about this trip was great. It was the trip of a lifetime. Our children had such a great time they can’t wait to come back. Thank you for a great villa and experience.
Stayed 7 nights in Apr 2022

10/10 Excellent

Jon A., New Era

Liked: Cleanliness

Extraordinary

An excellent property!
Stayed 5 nights in Mar 2022

10/10 Excellent

Jill D.

Liked: Cleanliness

Perfect property

Location, view, host, property manager and house layout all exceeded our expectations!
Stayed 14 nights in Jan 2022

6/10 Okay

gabrielle s.

Amazing View!

The property as a whole is a beautiful space! Patrick was so friendly before we even arrived and helped us with any questions we had. He even recommended an amazing taxi service to drive us everywhere since we did not rent cars. As far as the house itself, when we arrived a few of the sheets were dirty but we just took it upon ourselves to wash them in the washer and dryer that’s provided. The biggest issue I think was the water pressure. The house sleeps 12 people, I traveled with 10 people and only one person could shower at a time and even then it was only minimal water pressure. We addressed this issue to the property manager and Patrick and they were quick to respond but it did not fix the issue, as they stated they probably need to get a whole new water pump. We also ran out of gas one morning and were not able to use the stove until someone came and replaced the tanks later that night. When these issues were brought up, I feel as though they were addressed but not completely fixed nor did they offer any accommodation for the inconveniences. Another thing to note is that the property is in a “quiet” neighborhood and we did get some noise complaints around 7pm on our first night there. There is “quiet hours” after 9pm which we were aware of but the neighbors started to complain well before then so keep that in mind! On a positive note: the house was huge and the view was simply amazing! All issues aside, I’d definitely recommend staying here with your family!
Stayed 5 nights in Jan 2022

10/10 Excellent

Anne K.

Liked: Cleanliness

Phenomenal view

Believe it or not, the photos don't do the view from this home justice. It's absolutely amazing. We loved watching yachts, sea planes, and cruise ships come in and out of the various harbors and drinking rum punch while watching the sun set each night. The pool was clean and refreshing. Our teens loved having their own little suites complete with sitting rooms with televisions and excellent internet. The owners kept us up-to-date throughout the year on activities, COVID protocols, etc. and we felt very well informed. All in all we had a fabulous stay at this home.
Stayed 9 nights in Dec 2021

10/10 Excellent

lillian l.

Liked: Cleanliness

AMAZING!!!!!!

This place is Wonderful. Lots of room for everyone. The view was fabulous !!!!!! We will be returning next year.
Stayed 7 nights in Dec 2021

10/10 Excellent

Kathyf10 F.

Liked: Cleanliness

Amazing Experience

I can't say enough about this property, the owner and the property manager. It surpassed all of our expectations. The view, pool and rooms were gorgeous. The house met all of our needs. Thank you Southwind Villa for a great week.
Stayed 7 nights in Nov 2021

8/10 Good

Chemberli C.

Liked: Cleanliness

Beautiful property

I and my guest enjoyed the luxury of this property during our trip for my 50th birthday celebration! The natural scenery was amazing. The layout of this villa is perfect when traveling with multiple guests. We had so much privacy! I would recommend this property if you are traveling with a large group. It was definitely priced right, and we got more than we could've imagined for the price. Looking forward to coming back.
Stayed 4 nights in Oct 2021

10/10 Excellent

Pennie Z., Cape Canaveral, FL

Liked: Cleanliness

60th Birthday Celebration

We booked Southwind for my 60th birthday celebration. Southwind far exceeded our expectations! Southwind is AWESOME! The location of the bedrooms provided good privacy for each couple. The veranda and pool were our favorite gathering spots. The pool is very large and was wonderful, especially after a day full of activities. Pat and Jerscillia were wonderful. They made sure we were well taken care of. Pat sent us interesting facts about St Thomas all week. He was also most helpful with the planning process. We greatly appreciated it. Can’t wait to come back it was so wonderful!
Stayed 7 nights in Sep 2021

10/10 Excellent

Nailah F.

Liked: Cleanliness

It’s the view and the pool for me

This villa was amazing the view is incredible the amenities were off the chart the pool was great… I have nothing bad to say at all. Anytime I had a question it was answered promptly. I will be returning soon!!! Thanks for everything ❤️
Stayed 5 nights in Aug 2021

10/10 Excellent

Jon H.

Liked: Cleanliness

Southwind Villa

My family and I had an amazing time in St Thomas. Southwind Villa was the perfect location for us. Being in the center of the island made ever corner of St Thomas easily accessible. The view was spectacular and the layout of the house allowed everyone to have a bit of privacy when needed. The availability of a toddler bed for our son was a huge plus. The property was clean upon our arrival. Wifi signal was strong and worked perfectly everywhere except the lower level suite. Would absolutely stay again.
Stayed 7 nights in Jul 2021

10/10 Excellent

Tabitha T.

Liked: Cleanliness

Awesome views!

We had the best stay at Southwind Villa! Everything was perfect. It definitely has the best views in St. Thomas. We couldn’t have asked for a better location. Thanks again!
Stayed 5 nights in Jul 2021