Villa in Virgin Islands (U.S.)
12 guests · 6 bedrooms · 6 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this villa rental
Windsong is a secluded private estate located on the exclusive East End of St. Thomas. It is available to discerning, sophisticated travelers for the first time since 1974. The recently renovated and expanded (6) Master Suite, (8) BA Villa, sits atop a peninsula on the South East End of St Thomas on dramatic cliff's edge, 120’ feet above the Caribbean Sea.
Our guests enjoy stunning 210 degree views of Tortola to the North, the Cow & Calf reef and St. Croix to the South, Christmas Cove and St. John to the East, and majestic unobstructed sunsets over Fiddler’s Hat and the Caribbean to the West. Windsong is an idyllic setting for adult retreats and business conferences.
All (6) master staterooms enjoy private ensuite bathrooms, terraces, undisturbed views of the Caribbean Sea, and the beautiful gardens surrounding the 3.5-acre estate.
SMART TV's provide access to your favorite Apps Amazon Prime Music, Hulu & Netflix- Bring your own passwords!!
Amenity packages, in each of our professionally decorated, elegant, private suites provide for the ultimate in comfort, connectivity and luxury; allowing entrepreneurs and executives alike the opportunity to enjoy time away with family and friends.
Windsong is outfitted with a professionally designed and detailed gourmet kitchen, complete with state of the art Kitchen aid and GE Monogram appliances, granite counter tops, and every necessity your chef desires to prepare the finest meals imaginable.
Your dining experience can be enjoyed in our open air dining/great room or on the travertine terrace overlooking the reflections of the palm trees, in the fresh water, pool.
Architecturally designed by Scott Natvig the estate boasts a Tropical Modern style typical of the great luxurious estates of the Caribbean. The grounds are professionally landscaped and maintained showcasing exotic trees, lush gardens, and peaceful sitting areas for morning coffee and sunset gazing.
Windsong is destined to become the most sought after private retreat in the Caribbean. 6 Master suites, each approximately 400 sq ft. including soft seating areas and ensuite baths. Each shower is completed with glass or stone walls many providing open views to the Caribbean Sea. Travertine tiled walk-in showers, granite counter tops, Spanish cedar woodwork, custom built vanities and private travertine terraces facing to the North, South East and West throughout the home.
Approximately 1,500 Sq. ft. entertainment room offering billiards, soft seating, dining area, game table and an open bar. Fresh water upper pool in the garden terrace. Cliff side saltwater infinity edge lower pool 80' below main level.
Laundry facilities
Flat Screen T.V. in each room
Wireless Sonos sound system in throughout
Wireless Wi-Fi connectivity throughout the property
Outdoor Kitchen / Barbecue
Dining room / Great room can be arranged to cater to over 100 people for dinner and the property can accommodate over 150 for receptions and special events. Close by are 4 diamond restaurants and Resorts; The Ritz Carlton, The Elysian, The St. Thomas Yacht Club, Red Hook, American Yacht Harbor Marina, are all less than a 10-minute drive.
Everything you could possibly need to enjoy your time on the island is available on the East End of the Island: Yacht Charter Services, SCUBA diving, day sails, grocery store, butcher, restaurants bars and nightlife, rental car agencies, ferry services to all other island destinations, etc.
Private excursions can be provided to other locations by helicopter, plane or yacht. The jet and plane service is out of the airport downtown, yacht and boat charters will depart from American Yacht Harbor.
Due to its dramatic cliff-side positioning Villa Windsong is not suitable for families traveling with young children. The owner will be happy to review families traveling with children wanting to stay at Villa Windsong on a case by case basis.
Our guests enjoy stunning 210 degree views of Tortola to the North, the Cow & Calf reef and St. Croix to the South, Christmas Cove and St. John to the East, and majestic unobstructed sunsets over Fiddler’s Hat and the Caribbean to the West. Windsong is an idyllic setting for adult retreats and business conferences.
All (6) master staterooms enjoy private ensuite bathrooms, terraces, undisturbed views of the Caribbean Sea, and the beautiful gardens surrounding the 3.5-acre estate.
SMART TV's provide access to your favorite Apps Amazon Prime Music, Hulu & Netflix- Bring your own passwords!!
Amenity packages, in each of our professionally decorated, elegant, private suites provide for the ultimate in comfort, connectivity and luxury; allowing entrepreneurs and executives alike the opportunity to enjoy time away with family and friends.
Windsong is outfitted with a professionally designed and detailed gourmet kitchen, complete with state of the art Kitchen aid and GE Monogram appliances, granite counter tops, and every necessity your chef desires to prepare the finest meals imaginable.
Your dining experience can be enjoyed in our open air dining/great room or on the travertine terrace overlooking the reflections of the palm trees, in the fresh water, pool.
Architecturally designed by Scott Natvig the estate boasts a Tropical Modern style typical of the great luxurious estates of the Caribbean. The grounds are professionally landscaped and maintained showcasing exotic trees, lush gardens, and peaceful sitting areas for morning coffee and sunset gazing.
Windsong is destined to become the most sought after private retreat in the Caribbean. 6 Master suites, each approximately 400 sq ft. including soft seating areas and ensuite baths. Each shower is completed with glass or stone walls many providing open views to the Caribbean Sea. Travertine tiled walk-in showers, granite counter tops, Spanish cedar woodwork, custom built vanities and private travertine terraces facing to the North, South East and West throughout the home.
Approximately 1,500 Sq. ft. entertainment room offering billiards, soft seating, dining area, game table and an open bar. Fresh water upper pool in the garden terrace. Cliff side saltwater infinity edge lower pool 80' below main level.
Laundry facilities
Flat Screen T.V. in each room
Wireless Sonos sound system in throughout
Wireless Wi-Fi connectivity throughout the property
Outdoor Kitchen / Barbecue
Dining room / Great room can be arranged to cater to over 100 people for dinner and the property can accommodate over 150 for receptions and special events. Close by are 4 diamond restaurants and Resorts; The Ritz Carlton, The Elysian, The St. Thomas Yacht Club, Red Hook, American Yacht Harbor Marina, are all less than a 10-minute drive.
Everything you could possibly need to enjoy your time on the island is available on the East End of the Island: Yacht Charter Services, SCUBA diving, day sails, grocery store, butcher, restaurants bars and nightlife, rental car agencies, ferry services to all other island destinations, etc.
Private excursions can be provided to other locations by helicopter, plane or yacht. The jet and plane service is out of the airport downtown, yacht and boat charters will depart from American Yacht Harbor.
Due to its dramatic cliff-side positioning Villa Windsong is not suitable for families traveling with young children. The owner will be happy to review families traveling with children wanting to stay at Villa Windsong on a case by case basis.
Amenities at Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club
Free WiFi/internet
Air conditioning
Pool
Non-smoking
TV
Wheelchair accessible
Coffee/tea maker
Refridgerator
Kitchen
Balcony/Terrace
WiFi/Internet
Private pool access
Microwave
Dishwasher
Washing machine
Dryer
Patio
No pets allowed
Garden
Oven
Stove
Laundry services
Sofa bed
Children's high chair
Ironing facilities
Towels
Hairdryer
Map of Virgin Islands (U.S.)
Ratings and reviews
Summary of reviewsSpectacular views, amazing rooms with private baths, great for families and group gatherings. Property management is responsive and helpful. Guests blown away by the panoramic views.
10.0 / 10.0Outstanding·Aug 2025
Beautiful and unique property perfect for my family!
10.0 / 10.0Outstanding·Jul 2025
My family was blown away by this home!! We had to force ourselves to leave each time we had plans to go somewhere. Plenty of room and the accommodations were awesome. We will definitely book again if we ever get the chance.
10.0 / 10.0Outstanding·May 2025
We had an excellent stay at Windsong celebrating my husbands 50th birthday. The communication leading up to our stay was timely and the response time from James and his team was fantastic. The 6 bedrooms are beautiful, especially the master bedroom. Note, there is one bedroom on the lower level, that is not exactly nearby the other bedrooms, but it works. We had a chef come in to the Villa one night and that was a highlight of our trip. Getting to/from Red Hook for our excursions was easy and about a 7 - 10 min taxi ride. Warren is excellent to use all week for taxi services. I will say, some other taxi services we used during the week struggled to find the house and that was difficult at times. Taxi to the airport is about 25 - 30 minutes. The house was clean, each bedroom has a lock/key for your valuables and we all felt very safe. Also, having laundry facilities on the property was very helpful for towels, etc. We had 12 adults with plenty of space in the house. Overall, I highly recommend this property.
6.0 / 10.0Average·Feb 2021
We had high expectations for this property with the view and location. Property could be a 5 with some TLC.
This was our first house rental in the Caribbean so not sure if this condition is normal for the area, considering storm damage.
The view is amazing...from sunrise to sunset and beyond.
The main level outside area is nice with comfortable furniture. We spent most of our time together here. The layout is not the best for everyone hanging out together, upper pool is small and lower pool is 52 steps down, but wide rails supply lots of seating.
The lower pool is concerning as it appears that part of the decking/structure has fallen down the cliff and it is missing numerous tiles. I assume it is safe but it is extremely unattractive with the missing tiles and the debris on the cliff below the “infinity” edge.
The exterior grounds need debris clean-up as well.
The bedrooms are pretty and have been updated with new furniture, bedding, and windows. Mattresses are comfortable and sheets are nice.
The great room space is spacious and open. We enjoyed the bar and pool table. The doors in the great room are not very functional. We opened all that we could in the evening to capture the breezes. One set has been replaced and it works well, all others are difficult to open/close. We simply left them cracked open most of the time. Another set has been replaced with plywood...unattractive but it’s location doesn’t hamper the view.
The water pressure is minimal in some bathrooms, reducing to a trickle when more than one shower is used. There is also insufficient hot water for the size of the house.
The kitchen is functional, has an ice machine and 2 refrigerators... but could use a deep cleaning. We hired a chef for our dinners. It appeared to have what he needed (or he brought his own supplies.) The outdoor grill came in handy for lunches. The house does not have enough wine glasses for the number of guests. We borrowed some from the chef.
Overall, we enjoyed our week at Windsong, once we adjusted our expectations to an “island”house. Coffee in the morning with the sunrise and cocktails in the evening with the sunset. Some guests ran the stairs for an incredible workout. Pool table is fun evening activity.
Take binoculars if you go. The views of the surrounding islands and the gorgeous boats are amazing!
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Top rated by guests
9.4Outstanding
(30 Ratings)
Spectacular views, amazing rooms with private baths, great for families and group gatherings. Property management is responsive and helpful. Guests blown away by the panoramic views.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
