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Classic West Indies Retreat with Timeless Soul

Photo gallery for Classic West Indies Retreat with Timeless Soul

An aerial view of a house with a swimming pool, surrounded by dense greenery. - Classic West Indies Retreat with Timeless Soul (St. Thomas)
A covered patio area with wicker furniture, a ceiling fan, and large windows offering a view of the ocean. - Classic West Indies Retreat with Timeless Soul (St. Thomas)
A spacious living room with a dining area, a large window, and a ceiling fan. - Classic West Indies Retreat with Timeless Soul (St. Thomas)
A tropical garden with palm trees and a view of the ocean. - Classic West Indies Retreat with Timeless Soul (St. Thomas)
A bedroom with a bed, a dresser, a TV, and a window with blinds. - Classic West Indies Retreat with Timeless Soul (St. Thomas)
Close to Magens Bay Beach, Classic West Indies Retreat with Timeless Soul provides amenities such as a garden. Treat yourself to a massage or other spa services. Guests can connect to in-room WiFi.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning

Add dates for prices

About this property

Classic West Indies Retreat with Timeless Soul

  • Welcome to Villa Southwind—a 5-bedroom, 3-bath Caribbean villa perched above Charlotte Amalie Harbor on St. Thomas. Take in sweeping 180° panoramic views, unwind by your private pool, and enjoy modern comforts in a setting that captures Caribbean and Old West Indies charm the way it was meant to be: warm, welcoming, unhurried, and unforgettable. With space for up to 12 guests, you’re just minutes from downtown Charlotte Amalie’s vibrant shops, diverse restaurants, and historic charm, plus a short drive to pristine beaches—ideal for a serene island retreat with family or friends.

    ** There are extra guest fees after 10 guests.

    **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’ll help make sure we find you the best property to suit your specific needs, and 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.

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

Property amenities

Ski

  • Close to skiing

Pool/Spa

  • Massage
  • Private pool

Internet

  • Available in the villa: WiFi

Parking and transport

  • Car recommended
  • Parking on site

Kitchen

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

Dining

  • Breakfast available for a fee
  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • 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

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
  • Snorkelling 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)
  • Fire extinguisher

General

  • Garden

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 33

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Guests will be required to sign a rental agreement. 1. No parties or events 2. No smoking 3. Respect your neighbors 4. Enjoy!

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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

We should mention

A car is recommended for transport to and from this property

About the area

Located in St. Thomas, this villa is in the mountains. The area's natural beauty can be seen at Magens Bay Beach and Coki Point Beach. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and hiking/biking trails. Visit our Charlotte Amalie travel guide
View more Villas in Charlotte Amalie
Map
St. Thomas

What's nearby

  • A wooden cabinet with religious items, including a menorah, a shofar, and prayer books.
    St. Thomas Synagogue
    4 min drive - 2.1 km
  • A statue of a historical figure in a colonial-style building with a tower, surrounded by palm trees and benches.
    Blackbeard's Castle
    4 min drive - 2.4 km
  • Drake's Seat
    18 min walk - 1.5 km
  • Cathedral of St. Peter and St. Paul
    4 min drive - 2.1 km
  • 99 Steps
    4 min drive - 2.4 km

Getting around

  • St. Thomas (SPB-St. Thomas Seaplane Base)
    9 min drive

Restaurants

  • Taphus Beer House
    4 min drive
  • Cuttlas & Cane
    7 min drive
  • Rum Island Pub
    4 min drive
  • Virgilio's
    4 min drive
  • Sib's on the Mountain
    6 min walk

Frequently asked questions

Is Classic West Indies Retreat with Timeless Soul pet-friendly?

No, pets are not allowed at this property.

How much is parking at Classic West Indies Retreat with Timeless Soul?

On-site parking is available at the property.

What time is check-in at Classic West Indies Retreat with Timeless Soul?

Check-in begins at 4:00 PM.

What time is check-out at Classic West Indies Retreat with Timeless Soul?

Checkout is at 11:00 AM.

Where is Classic West Indies Retreat with Timeless Soul located?

Situated in the mountains, this villa is 0.8 mi (1.2 km) from Drake's Seat and 2.8 mi (4.5 km) from Magens Bay Beach. Blackbeard's Castle and St. Thomas Synagogue are also within 1 mile (2 km).

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Reviews

Classic West Indies Retreat with Timeless Soul Reviews

9.6

Exceptional

9.6

Cleanliness

9.6

Location
Rating 10 - Excellent. 37 out of 45 reviews
Rating 8 - Good. 5 out of 45 reviews
Rating 6 - Okay. 2 out of 45 reviews
Rating 4 - Poor. 1 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

Reviews

Verified review

10/10 Excellent

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

Lissette manor

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

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

8/10 Good

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
Verified review

8/10 Good

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house in the Hills, 10 mins away from the city. Amazing views..
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Extraordinary

An excellent property!
Stayed 5 nights in Mar 2022
Verified review

10/10 Excellent

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
Verified review

8/10 Good

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

8/10 Good

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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