Entire home

5br with Huge pool and fantastic harbor views!

Photo gallery for 5br with Huge pool and fantastic harbor views!

Pool
Terrace/patio
Outdoor dining
Room
Living area

Reviews

9.6 out of 10
Exceptional
5 bedrooms4 bathrooms

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Pool
  • Breakfast available
  • Kitchen

Explore the area

Map
St. Thomas, St. Thomas
  • Blackbeard's Castle
    ‪4 min drive‬
  • Yacht Haven Grande Marina
    ‪7 min drive‬
  • Magens Bay Beach
    ‪8 min drive‬
  • St. Thomas (SPB-St. Thomas Seaplane Base)
    ‪9 min drive‬

Rooms & beds

5 bedrooms

Bedroom 1

1 King Bed

Bedroom 2

1 Single Bed, 1 Queen Bed and 1 Single Bunk Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

1 King Bed

4 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining area

About this property

5br with Huge pool and fantastic harbor views!

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
Premier Host

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Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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About the area

Charlotte Amalie

Map
St. Thomas, St. Thomas

What's nearby

  • Blackbeard's Castle - 4 min drive - 2.4 km
  • 99 Steps - 4 min drive - 2.5 km
  • Yacht Haven Grande Marina - 7 min drive - 4.8 km
  • Magens Bay Beach - 8 min drive - 4.8 km
  • Magens Bay - 10 min drive - 5.5 km

Restaurants

  • ‪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
  • ‪Taphus - ‬4 min drive

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Pamela C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

Lissette manor

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

10/10 Excellent

Sarah M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

Thomie T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

8/10 Good

Carol D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

Jill D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect property

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

10/10 Excellent

Jon A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Extraordinary

An excellent property!
Stayed 5 nights in Mar 2022

10/10 Excellent

Shemariah p.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing place to celebrate my 40th birthday

Thanks for having us stay with you , perfect location , beautiful villa , the view absolutely amazing looked just like the pictures thank you for allowing me to enjoy my visit home and celebrate with family and friends to bring in turning 40 I could not have asked for more
Stayed 6 nights in Jan 2021

10/10 Excellent

Tabitha T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

lillian l.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

8/10 Good

Kim D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun Week

Enjoyed a week with our friends at this great property. Provided pretty views and great entertainment areas for all to enjoy. Being at the top of the mountain, expect some drives to downtown or Redhook for trips outside of the house.
Stayed 7 nights in Dec 2020

10/10 Excellent

Stephanie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Michelle K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay at Southwind Villa!

We had an amazing trip to St Thomas and the perfect stay at Southwind Villa. The view is spectacular and the accommodations were great. We were so appreciative of the attentive service and responses by Pat and Jerscillia. We will absolutely be back! Thank you for helping us create memories to last a lifetime!
Stayed 8 nights in Mar 2021

10/10 Excellent

lillian l.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!!!!!

The property was Beautiful!!!! When we return to St. Thomas, we will book this home again. It will be our first choice. The views are amazing!!!!! Great location. The owners of this home were very attentive.
Stayed 7 nights in Dec 2020

10/10 Excellent

Jason B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

Kathyf10 F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

David L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Host was AWESOME

Phenomenal communication and coordination from the get-go with the property management team, including logistical/transportation help and tips on things to do in the area. The house itself was clean, the photos were accurate (better in real-life, actually), and the views were incredible.
Stayed 5 nights in Mar 2020

10/10 Excellent

James K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Keva M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful villa

I couldn't have picked a better villa for my 40th celebration. It was the perfect fit for five couples. It was full with everything that we possibly needed, down to rum punch mix. I will definitely be back soon.
Stayed 4 nights in Jan 2020

8/10 Good

Chemberli C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

8/10 Good

Kenneth F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

Barbara B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful getaway

We thoroughly enjoyed our stay at Southwind Villa. The house accommodated us well, affording privacy when needed but also opportunity for together time. We loved the amazing view—one of the best we’ve ever experienced! That porch was where we spent so much of our time, and the large pool was wonderful. Best of all, though, were our hosts. Pat and Sally could not have done more to make our stay enjoyable. They are truly outstanding.
Stayed 9 nights in Feb 2021

10/10 Excellent

Nailah F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Trey R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Terrific Vacation at Southwind Villa

Our family enjoyed a wonderful week at Southwind Villa in St. Thomas. The location of Southwind Villa in a secluded and secure neighborhood is central to everything in St Thomas, offering easy access to Magen's Bay, Charlotte Amalie, and Red Hook. We enjoyed breakfast everyday on the spacious veranda overlooking the port at Charlotte Amalie and spent every evening on the veranda enjoying the tranquility and cool mountain breeze. The property owner was a gracious host who went above and beyond to ensure we had an outstanding stay at this jewel of the Caribbean. We look forward to returning in the future.
Stayed 7 nights in Apr 2021

10/10 Excellent

Jon H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

About the host

Hosted by Justin Thomas

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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