Perched on the East End of St. Thomas, Windsong offers guests a secluded retreat with unparalleled ocean views and dramatic sunrises and sunsets. This 6-bedroom villa boasts a spacious Great Room, outdoor dining areas, an open kitchen equipped with state-of-the-art appliances, granite countertops for private chef meal preparation plus plenty of space for groups or receptions.
Windsong is a private, secluded villa situated on a dramatic cliff edge on the East End of St. Thomas. This masterfully designed villa offers guests unparalleled and unobstructed ocean views and fantastic sunrises and sunsets. The location boasts 210 degree-views of the British Virgin Islands, St. John, Christmas Cove, and St. Croix.
Whether traveling with family or groups, Windsong`s 6 bedrooms and 8 (6 ensuite, 2 half) baths ensure plenty of space and privacy as you enjoy all that St. Thomas has to offer. The villa is also able to accommodate 50 guests for receptions, weddings, and other special events.
The spacious and open Great Room, Dining Room, and Kitchen are the villas main gathering areas with additional outdoor chairs, sofas, and lounge chairs throughout the property. An outdoor dining table is located off the Great Room next to the pool. The kitchen is equipped with state-of-the-art appliances, granite countertops, and all the necessities your chef needs to prepare meals.
Windsong`s convenient East End location puts you within minutes of fantastic fine dining options at the St. Thomas Yacht Club, The Ritz-Carlton, and a number of restaurants in Red Hook. Red Hook and American Yacht Harbor are also home to numerous fishing charters, day-boat charters to the BVI, parasailing, snorkeling, and scuba tours.
***Does this property not fit your entire party? We have additional properties minutes away for groups willing to split up into multiple villas.
**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.**
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, you will never be left high and dry. 5.We provide a 24/7 maintenance and emergency hotline.
The property is 100% private and for your use exclusively.
Windsong is located on Deck Point, a gated, private peninsula on the east end of St. Thomas. Close to St. Thomas Yacht Club and only a 5 minute drive to Red Hook, which features many restaurants, shops, a marina, and the ferry to the BVI and St. John!
We suggest renting a vehicle, however we are happy to arrange other transportation if you’d like.
We offer all our guests a full-service concierge, free of charge! 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
Pool/Spa
Massage
Private pool
Internet
Available in the villa: Free WiFi
Parking and transportation
Car recommended
Wheelchair-accessible parking and van parking available
Onsite parking options include a garage
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Ice maker
Kitchen island
Microwave
Oven
Refrigerator
Spices
Stovetop
Toaster
Dining
Breakfast available for a fee
Dining table
Bedrooms
6 bedrooms
Bedsheets provided
Bathroom
7 bathrooms
Hair dryer
Towels provided
Living spaces
Dining table
Living room
Separate dining area
Entertainment
Books
Smart TV with cable/satellite channels
Stereo
Outdoor areas
Balcony
Barbecue grill
Garden
Laundry
Laundry facilities
Washing machine
Work spaces
Desk
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.
1 accessible parking space
1 step to reach entrance
Area rugs in public areas
Tile flooring in public areas
Upper floors accessible by stairs only
Well-lit path to entrance
Wheelchair-accessible parking
Wheelchair-accessible pool
Wheelchair-accessible van parking
Smoking not allowed
Services and conveniences
Housekeeping (on request)
Iron/ironing board
Meal delivery service
Location highlights
Near a health/beauty spa
Near a hospital
Near the bay
Near the marina
Near the ocean
On the waterfront
Things to do
2 outdoor pickleball courts
Billiards/pool table
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)
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
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
Parties and events are allowed on site
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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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 transportation to and from this property
About the neighborhood
Located in St. Thomas, this villa is on the waterfront. The area's natural beauty can be seen at Sapphire Beach and Virgin Islands National Park. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and ecotours nearby. Visit our St. Thomas travel guide
What time is check-in at 6 BR - Unparalleled 220º Views, Breathtaking Oceanfront Location & 2 Pools!?
Check-in begins at 4:00 PM.
What time is check-out at 6 BR - Unparalleled 220º Views, Breathtaking Oceanfront Location & 2 Pools!?
Check-out is at 11:00 AM.
Where is 6 BR - Unparalleled 220º Views, Breathtaking Oceanfront Location & 2 Pools! located?
Situated on the waterfront, this villa is 0.2 mi (0.3 km) from Cowpet Bay and 2.5 mi (4.1 km) from Sapphire Beach. Turquoise Beach and Cabrita Point are also within 2 mi (3 km).
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All reviews shown are from real guest experiences. Only travelers 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.
The view is incredible! Justin, the host, communicated well with timely responses thru out our stay. They also offer many conveniences such as in house chef, in house yoga, in house spa treatments and grocery delivery.Would recommend full length mirrors in all bedrooms and more washcloths for each person. Had a great time! Thank you!
Darla S.
Stayed 7 nights in Jan 2026
Verified
10/10 Excellent
William
20 July 2025
Liked: Amenities, property conditions & facilities, communication
Great vacation home. Mgmt helped with all issues and booking trips and chef Durant was great for our dine in night. Great island location and breathtaking views. RedHook is handy location. Would recommend
The property was accurately shown on the website. The space was more than enough for my guests and the double pools were great. The common area was spacious and we used it often. The door from the dining area to the pool needs to be replaced so it does lose cool air , but that was the only thing that we could say bad about the place. It is a must stay
Great location and house! The management group was very responsive to any issues with the property and the concierge was very helpful. The house does need some maintenance but still very comfortable. I would rent this property again.
The views are spectacular! We watched the sunset from the west deck every evening. The bedrooms were not attached to the great room so us "older" people could go to bed while the younger crowd stayed up late. Justin and his crew were very accessible. They even delivered a new grill the same day we called about it.
Thanks for a great week!
Our group of 10 seniors loved this property! Amazing views from the large common area. Plenty of space to be together but also lots of areas for private time. Three suites with same-level access to the main area and three suites requiring one set of steps to access. One pool on the main level and one pool down near the ocean for the more adventurous. The property manager responded immediately when we needed a bit of repair work done- problem solved right away. All in all, a wonderful and relaxing experience!
This is a fabulous venue for wedding photos...even the wedding help were taking photos! Justin and Meghen from the property management company couldn't have been better...they met ever demand and exceeded all our expectations. You will be hard pressed to find a better group to do business with.
The only drawback of the property is that it is hard to find as it is on a cliff at the end of a road. Also, it is surrounded by ocean but one is unable to reach it to swim if you're on foot.
Property is spacious and really liked that the interior common areas are separate from the rooms so you have privacy. The view is amazing from every room. Everything was functional and whatever was not working the maintenance crew would address right away. The property needs some upkeep as the conditions are not as good as the pictures. The gas stove doesn’t start unless you have a lighter and the knobs are not necessary accurate. The wood and glass doors in the family don’t open. Balcony rails are showing rust. The lower pool is missing tiles and has some stains. The upper pool needs a new bottom job. We had rain and when it rained we had water leaks from ceiling by the bar and one bedroom upstairs.
This property has the most spectacular ocean views! I just got married here and the palm trees by the pool deck made for a picturesque backdrop. We booked this villa for 8 people across 4 days. The property is huge and we never felt like we didn’t have enough room. One thing to note is the villa is a bit hard to find, so we recommend hiring a driver who knows what they are doing, shout-out to Warren!! The villa is a bit outdated (70s?) and the door going out to the pool deck gets stuck on the ground. One of the rooms had a weird smell, but contacting the property manager was so easy and they came out right away to fix it. One thing that would be helpful is sending a layout map of the villa to the guests ahead of time so we can figure out the rooms before getting there. We first put my parents in the pirate cove, but upon getting there the room is not easily accessible and you have to go outside to access it. Once we figured out the layout we changed the room assignments. All in all I would highly recommend staying here. Great location (close to red hook), secluded, picturesque views, and so many great entertainment areas!
Great lil place, great host, will stay again when visiting family who live in town.
Jeff H.
Stayed 5 nights in Jun 2025
Verified
6/10 Okay
Jeff H.
25 July 2021
Liked: Check-in, communication, location
Disliked: Listing accuracy
If only it was as nice as the pictures
Doors from the living area to outside are only partially operable. Some you can not open. Roof leaks A LOT in the living area all over the pool table and floor. The ac units can’t cool properly due to large gaps between the doors and door jams. Pool is maybe half the size it appeared online. The bottom pool should be condemned.