Title: Classic West Indies Retreat with Timeless Soul - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Classic West Indies Retreat with Timeless Soul Villa in St. Thomas with private pool and kitchen ## Photo gallery for Classic West Indies Retreat with Timeless Soul ![Pool - Classic West Indies Retreat with Timeless Soul (St. Thomas)](https://images.trvl-media.com/lodging/116000000/115180000/115176800/115176729/w1348h894x0y3-3314457d.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior - Classic West Indies Retreat with Timeless Soul (St. Thomas)](https://images.trvl-media.com/lodging/116000000/115180000/115176800/115176729/65bbbe66.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - Classic West Indies Retreat with Timeless Soul (St. Thomas)](https://images.trvl-media.com/lodging/116000000/115180000/115176800/115176729/a5a4a852.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Classic West Indies Retreat with Timeless Soul (St. Thomas)](https://images.trvl-media.com/lodging/116000000/115180000/115176800/115176729/999c47ba.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Classic West Indies Retreat with Timeless Soul (St. Thomas)](https://images.trvl-media.com/lodging/116000000/115180000/115176800/115176729/674d6d8b.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Close to Magens Bay Beach, Classic West Indies Retreat with Timeless Soul provides amenities like a garden and laundry facilities. Guests can connect to free in-room WiFi. ## Reviews 9.6 Exceptional ### Entire home 5 bedrooms4 bathrooms ## Popular amenities - Pool - Kitchen - Washer - Dryer - Free WiFi - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## 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. 1\. No parties or events 2\. No smoking 3\. Respect your neighbors 4\. Enjoy! ## Property amenities ### Ski - Close to skiing ### Pool/Spa - Private pool ### Internet - Available in the villa: Free WiFi ### Parking and transportation - Car recommended - Wheelchair-accessible parking available ### 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 ### Pets - No pets allowed ### 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 - Upper floors accessible by stairs only - Well-lit path to entrance - Wheelchair accessibility - Wheelchair-accessible parking - Smoking not allowed ### 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 ## Similar properties ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117880000/117876800/117876766/320bc0b0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Northside Villa, Pool + Views, Near Magens Bay St Thomas - Pool - Washer - Dryer - Air conditioning [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-03&endDate=2026-01-04&selected=117876766&PinnedHotelID=117876766&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88640000/88637200/88637166/6b010b0e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 6 Bedroom Ensuite Villa with Ocean Views, Private Saltwater Pool, Tropical Gardens St. Thomas - Ocean view - Pool - Kitchen - Washer 10 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-03&endDate=2026-01-04&selected=88637166&PinnedHotelID=88637166&HadPinnedHotel=true®ionId=-1&adults=2) ![TV](https://images.trvl-media.com/lodging/90000000/89640000/89639300/89639243/00b499a7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### "The LOFT" at Wintberg Place Rosendal - Kitchen - Washer - Dryer - Air conditioning 10 Exceptional 7 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-03&endDate=2026-01-04&selected=89639243&PinnedHotelID=89639243&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool](https://images.trvl-media.com/lodging/78000000/77140000/77130100/77130076/62bb96a8.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 3 Villas,One Price/ Sleeps 16/ Steam Room/Private Pool/Close to everything Gated St Thomas - Pool - Kitchen - Washer - Dryer 10 Exceptional 24 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-03&endDate=2026-01-04&selected=77130076&PinnedHotelID=77130076&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/51000000/50780000/50779700/50779649/dd319f5a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Private Waterfront 5 Bedroom Villa! 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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 transportation to and from this property ### Property is also known as 381829 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C18.35084%2C-64.93022&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=1_H8KqNQTm98wxobE6iba_Fxr6Q=) St. Thomas, St. Thomas #### What's nearby - Blackbeard's Castle \- 14 min walk \- 1.3 km - Frenchtown \- 15 min walk \- 1.3 km - St. Thomas Synagogue \- 16 min walk \- 1.4 km - Fort Christian \- 20 min walk \- 1.7 km - Magens Bay \- 4 min drive \- 2.4 km #### Getting around - Cyril E. King Airport (STT) - 20 min drive #### Restaurants - ‪Virgilio's - ‬4 min drive - ‪Green House Bar & Restaurant - ‬4 min drive - ‪Sib's on the Mountain - ‬6 min walk - ‪Ideal Restaurant - ‬5 min drive - ‪Mafolie Hotel & Restaurant - ‬11 min walk ## Frequently asked questions ### Is Classic West Indies Retreat with Timeless Soul pet-friendly? ### How much is parking? ### What time is check-in at Classic West Indies Retreat with Timeless Soul? ### What time is check-out at Classic West Indies Retreat with Timeless Soul? ### Where is Classic West Indies Retreat with Timeless Soul located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Classic West Indies Retreat with Timeless Soul Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 36 8 - Good 5 6 - Okay 2 4 - Poor 1 2 - Terrible 0 ### 9.4 Cleanliness ### 9.6 Location ## Reviews ### 10/10 Excellent #### James Y. Dec 29, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Lissette manor Amazing!! Loved the house and location. ##### James Y. Stayed 8 nights in Dec 2024 ### 10/10 Excellent #### Pamela C. Feb 18, 2025 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! ##### Pamela C. Stayed 5 nights in Feb 2025 ### 10/10 Excellent #### Sarah M. Jul 26, 2024 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 ##### Sarah M. Stayed 7 nights in Jul 2024 ### 10/10 Excellent #### Thomie T. Jan 12, 2023 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.! ##### Thomie T. Stayed 5 nights in Dec 2022 ### 10/10 Excellent #### Jill D. Feb 10, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect property Location, view, host, property manager and house layout all exceeded our expectations! ##### Jill D. Stayed 14 nights in Jan 2022 ### 10/10 Excellent #### Shemariah p. Jan 26, 2021 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 ##### Shemariah p. Stayed 6 nights in Jan 2021 ### 10/10 Excellent #### Jon A. Mar 13, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Extraordinary An excellent property! ##### Jon A. Stayed 5 nights in Mar 2022 ### 10/10 Excellent #### Tabitha T. Jul 20, 2021 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! ##### Tabitha T. Stayed 5 nights in Jul 2021 ### 8/10 Good #### Kim D. Jan 4, 2021 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. ##### Kim D. Stayed 7 nights in Dec 2020 ### 10/10 Excellent #### lillian l. Dec 10, 2021 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. ##### lillian l. Stayed 7 nights in Dec 2021 ### 10/10 Excellent #### Stephanie R. Apr 23, 2022 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. ##### Stephanie R. Stayed 7 nights in Apr 2022 ### 10/10 Excellent #### Michelle K. Mar 18, 2021 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! ##### Michelle K. Stayed 8 nights in Mar 2021 ### 10/10 Excellent #### lillian l. Dec 22, 2020 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. ##### lillian l. Stayed 7 nights in Dec 2020 ### 10/10 Excellent #### Jason B. May 18, 2022 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! ##### Jason B. Stayed 7 nights in May 2022 ### 10/10 Excellent #### Kathyf10 F. Dec 1, 2021 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. ##### Kathyf10 F. Stayed 7 nights in Nov 2021 ### 10/10 Excellent #### David L. Mar 20, 2020 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. ##### David L. Stayed 5 nights in Mar 2020 ### 10/10 Excellent #### Keva M. Feb 29, 2020 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. ##### Keva M. Stayed 4 nights in Jan 2020 ### 10/10 Excellent #### James K. Jul 2, 2022 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. ##### James K. Stayed 6 nights in Jun 2022 ### 8/10 Good #### Chemberli C. Oct 20, 2021 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. ##### Chemberli C. Stayed 4 nights in Oct 2021 ### 8/10 Good #### Carol D. Jul 9, 2024 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. ##### Carol D. Stayed 7 nights in Jun 2024 ### 10/10 Excellent #### Barbara B. Mar 3, 2021 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. ##### Barbara B. Stayed 9 nights in Feb 2021 ### 10/10 Excellent #### Nailah F. Sep 8, 2021 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 ❤️ ##### Nailah F. Stayed 5 nights in Aug 2021 ### 10/10 Excellent #### Trey R. Apr 12, 2021 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. ##### Trey R. Stayed 7 nights in Apr 2021 ### 10/10 Excellent #### Jon H. Jul 30, 2021 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. ##### Jon H. Stayed 7 nights in Jul 2021 ### 10/10 Excellent #### Ambika S. May 24, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Ambika S. Stayed 4 nights in May 2022