A family-friendly stay in St. Thomas awaits you at this villa. You'll be within a 10-minute walk of Cowpet Bay and 4.1 km (2.5 mi) from Sapphire Beach. .Villa features a private pool, a washing machine and free WiFi. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. 6 bathrooms, a balcony and a sofa bed are also available. Housekeeping is available on request.
You'll have the entire home to yourself and will only share it with other guests in your party.
Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club
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.
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
In-room accessibility
Smoke-free property
Note from host: Only Outside
Services and conveniences
Concierge services
Housekeeping (on request)
Iron/ironing board
Phone
Location highlights
Near a health/beauty spa
Near a hospital
Near the marina
Near the ocean
On the waterfront
Things to do
Arcade/game room
Billiards/pool table
Tennis
Water sports equipment
Birdwatching nearby
Ecotours nearby
Fishing nearby
Hiking/biking trails nearby
Horseback riding nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Parasailing nearby
Rock climbing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Surfing/bodyboarding nearby
Swimming nearby
Water skiing 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
General
Garden
Housekeeping (on request)
Unit size: 6,000 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25
Check-out
Check-out before 11:00 AM
Contactless check-out
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Pets
No pets allowed
Children and extra beds
Children are welcome.
Note from host: children must follow policies regarding cliff
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 first aid kit
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a smoke detector and a first aid kit in all accommodation.
Property is also known as
Everlasting Memories Villa St Thomas
Everlasting Memories St Thomas
Everlasting Memories
Frequently asked questions
Are there any beaches close to Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club?
The closest beach to Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club is Sapphire Beach (2.5 km).
Does Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club have a pool?
Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club has a pool.
What luxury perks are available at Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club?
This property features an outdoor pool, as well as a private pool and a living room.
Is Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club family-friendly?
You bet! With amenities such as an arcade, laundry facilities and highchairs, it's no surprise that Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club is a winner with our family travellers.
Is there a private hot tub at Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club?
No, but there is a private pool.
Is there a free airport shuttle available at Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club?
No, Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club does not offer an airport shuttle service.
What time are check-in & check-out at Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club?
Check-in begins at 4:00 PM. Check-out time is 11:00 AM.
Are pets allowed at Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club?
No, pets are not allowed.
Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club Reviews
Reviews
9.8
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.
Rating 10 - Excellent. 23 out of 26 reviews
10 - Excellent
23
Rating 8 - Good. 1 out of 26 reviews
8 - Good
1
Rating 6 - Okay. 2 out of 26 reviews
6 - Okay
2
Rating 4 - Poor. 0 out of 26 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 26 reviews
2 - Terrible
0
9.2/10
Cleanliness
Reviews
10/10 Excellent
Scott J.
27 July 2025
Liked: Cleanliness
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.
Scott J.
Stayed 4 nights in Jul 2025
10/10 Excellent
Katelyn B., Woburn MA
5 May 2025
Liked: Cleanliness
Amazing Stay at this Stunning Villa
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.
Katelyn B.
Stayed 7 nights in Apr 2025
10/10 Excellent
Thomas S.
15 Feb 2025
Liked: Cleanliness
40th Birthday
Enjoyed my 40th birthday at Windsong with my family. The property was nothing short of spectacular and the location was perfect. Can’t wait to come back!
Thomas S.
Stayed 4 nights in Feb 2025
10/10 Excellent
nick s.
9 Jan 2025
Liked: Cleanliness
Stunning Views
This property was just right for our party of 12. The views were amazing and the lower pool was a great spot to hang out.
nick s.
Stayed 7 nights in Dec 2024
10/10 Excellent
Frank G., Hydes, MD
28 Mar 2024
Liked: Cleanliness
Beautiful locations and home--not for kids!
The views from the patio and pool over to Christmas Cove are spectacular. Loved both pools-bit of a climb to and from the lower pool. With no guard rails I wouldn't suggest little kids at this house. Bedrooms all with private en suite baths were great for 5 couples.
Frank G.
Stayed 7 nights in Mar 2024
10/10 Excellent
Larissa P.
16 Mar 2024
Liked: Cleanliness
Spring Break
Great House in a great location. We enjoyed our first trip to St. Thomas! The house was perfect for our group of 8.
Larissa P.
Stayed 8 nights in Mar 2024
10/10 Excellent
Verified traveller
15 Mar 2024
Liked: Cleanliness
Loved windsong
This was a beautiful property with amazing views. The Rooms were amazing each with their own bathroom and shower. We brought our kids and they had a wonderful time. Our youngest was 8, so the property being on a cliff was not a problem. Great response and check in from the management company. It was a dream vacation.
Verified traveller
Stayed 11 nights in Feb 2024
10/10 Excellent
MICHAEL P.
17 Aug 2023
Liked: Cleanliness
Absolutely beautiful !
Our stay was amazing. All our guests were blown away by the panoramic views of St. Thomas. The all separate master suites were just perfect. Thank you for a wonderful stay!
MICHAEL P.
Stayed 5 nights in Aug 2023
10/10 Excellent
Pamela G.
21 May 2023
Liked: Cleanliness
The view is amazing & totally priceless!!!! Everyone had their own private space.
I celebrated my 50th birthday at Windsong Villa. The concierge provided us with grocery delivery service, private chefs, on-site massage technicians, limousine, and tours information. The villa has everything except direct access to the beach. Other than that, you don’t have to leave the villa at all. The property management response quickly and handle any issues immediately. I would definitely recommend Windsong Villa to family and friends!!!! We will be back!!!
Pamela G.
Stayed 8 nights in May 2023
10/10 Excellent
Jon D.
29 Mar 2023
Liked: Cleanliness
Great
Incredible spot with incredible views
Jon D.
Stayed 5 nights in Mar 2023
10/10 Excellent
James L.
17 July 2022
Liked: Cleanliness
House was amazing and the view was incredible
It was a great property and highly recommended it. I would absolutely stay there again
James L.
Stayed 5 nights in Jul 2022
10/10 Excellent
Cathy E.
18 Dec 2021
Liked: Cleanliness
“Heaven on Earth”
We SO enjoyed our stay! Loved having each our own suites and coming together in the common area. The pool table was fun (though the sticks are missing the end but we didn’t care!). The view was incredible! A friend kept repeating “this is heaven on earth!” We had come together to attend a wedding and Windsong was perfect for us.
Cathy E.
Stayed 5 nights in Dec 2021
10/10 Excellent
Brian D.
15 Aug 2021
Liked: Cleanliness
Incredible Stay At The Villa Windsong!
We had an incredible week-long stay in August 2021 at the Villa Windsong! The views were absolutely spectacular, the large open kitchen and living area provided ample space for our guests to gather, and the six separate lockable bedrooms with their own spacious bathrooms provided comfort after long days of activities. After reading reviews prior to our arrival, we were prepared the villa had some issues with age, but we found everything to be acceptable and we would definitely recommend and stay at the Villa Windsong again in the future! Justin and Edie from Prestige were AMAZING to work with to plan activities associated with our stay to include arrival provisions, arrival platters and cocktails, snorkel rentals for the week, a private dinner for 16 people, an all-day yacht excursion, housekeeping, in villa massages, and recommendations for surrounding activities and points of interest.
Brian D.
Stayed 7 nights in Aug 2021
8/10 Good
Thomas H.
28 May 2021
House is in a prime location although poorly maintained.
The house is totally under maintained, second day on property rained all day. Kitchen, bar area, bedrooms totally soaked. Texted and emailed the property owner and property manager with no response. Chef that was recommended was amazing (Baja Bites). The chef was the best part of the trip. Very few beach towels were provided as well as very few toiletries. The pool as previously stated in other reviews is in major disrepair. The doors leading out to the patio area are old and don’t open easily. The house is has a wonderful view but lacks a lot of the the 5 star qualities it portrays to have. I like the location but would never rent again.
Thomas H.
Stayed 6 nights in May 2021
6/10 Okay
Leslie G.
16 Feb 2021
Beautiful views, needs some TLC
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!
Leslie G.
Stayed 7 nights in Jan 2021
6/10 Okay
nicole p., marion
6 Aug 2020
Beautiful but a little disappointing
House looks absolutely gorgeous online with amazing views and the booking transaction was smooth. However someone was suppose to meet us at the villa to let us in and show us the ins and outs (gate access, keys, WiFi, etc) First we were dropped a pin for the location of the villa and given the address however there were no numbers for this particular villa and it is difficult to find without proper instruction. It is tucked away behind another house that when you pull into the driveway you assume you are at the wrong place (hence no signs or numbers for villa). We had to park and call/text property manager and after no response we asked some neighbors if they knew where this villa was which they did. So we drive up a long curvy driveway to find the villa tucked away with no clear markings and again no one to meet us. We knock and walk in praying we are indeed in the right place. Keys, cards and a clicker laying on the counter with no idea of what they go to. That’s just the beginning... Dead roaches and traps everywhere, WiFi not working, infinity pool looks like it needs an overhaul (tiles coming off, loose debris around pool, rusty) very uninviting and picture listed is misleading. Each room has its on AC unit with about half working wonderfully and the other half leaving you sweaty with the need for cooler air. One of the beds completely broke when sat on and had to have maintenance come take it apart and put all no slates on the bed. While there, cyclone 9 was forming in the ocean, no worries for us bc we had a generator and were told it had just been serviced the week before. Well power goes out and guess what generator doesn’t work and apparently needs to be completely rebuilt so we were told “sorry” once again and left with no electricity or running water for over 12 hours with 5 kids. Did I mention they boarded everything up and brought all outdoor furniture (a lot of furniture) inside. Very uncomfortable situation and I don’t mean the storm. The storm was just high winds and welcomed since we had no AC and mosquitoes eating us alive. So WiFi was fixed rather quickly but would go in and out and eventually just out and we were told it was the weekend and they didn’t want to bother the one person who apparently knew how to fix it. The cards and clicker I mentioned were for the gate to the property but clicker didn’t work. Overall great potential but leaves much to be desired for the hefty price tag!!!
nicole p.
Stayed 7 nights in Jul 2020
10/10 Excellent
sir e.
7 July 2020
Liked: Cleanliness
Wonderful stay with an amazing view.
Villa windsong was an amazing stay with a beautiful view. The memory of staying in the house will be with us forever. We really enjoyed our stay and look forward to visiting again.
sir e.
Stayed 5 nights in Jun 2020
10/10 Excellent
Anne C.
25 Feb 2020
Liked: Cleanliness
A Week in Paradise
We recently spent a week in St. Thomas at Wind Song, an estate aptly named. With a spectacular view and soft summer breezes, our family was truly enchanted. The layout of the villa was perfectly suited for adults and made for some enjoyable family fun. We were so impressed with the services that were offered , especially those of Meghan See, our concierge and Chef, Colin Auchincloss whose culinary skills are unparalleled.
Anne C.
10/10 Excellent
john m., Milwaukee, WI
7 Jan 2020
Liked: Cleanliness
Terrific spot for a large group. Would consider Villa Windsong again without a doubt.
The process to rent was easy. Justin the property manager was great. Warren the local taxi driver was extremely flexible and available when needed. Our week spent in St Thomas with iur growing family was awesome.
john m.
Stayed 7 nights in Dec 2019
10/10 Excellent
Tara S.
21 Oct 2019
Liked: Cleanliness
Great house with fantastic views!
From the moment we booked the house we had excellent service by both Danny and Justin as well as the whole Prestige Team! A few minor issues that were taken care of while we were visiting! Fabulous place to stay!
Tara S.
10/10 Excellent
Michael p.
21 July 2019
Liked: Cleanliness
Vacation!’
Great view of the water and surrounding area. Loved it every day!!
Michael p.
Stayed 7 nights in Jul 2019
10/10 Excellent
Pat J.
30 June 2019
Liked: Cleanliness
Paradise Found
Can’t say enough nice things about our stay. The house was perfect for our family. Nice linens and a glorious view. Justin the manager is a jewel. Thanks for sharing your little piece of heaven. Pat Jarvis
Pat J.
Stayed 6 nights in Jun 2019
10/10 Excellent
Wanda W., Columbia
20 Apr 2019
St. Thomas - Villa Windsong
Villa Windsong is such an awesome house! The best view ever!! We didn’t want to leave today and Mark -the property manager and Danny the owner are so wonderful and helpful!
We will be back next year!! Can’t wait!
Wanda W.
Stayed 8 nights in Apr 2019
10/10 Excellent
Daniel H.
18 Mar 2019
Overwhelming beauty inside and out
The friendly staff met us on the East End and guided us to Villa Windsong. What a fantastic surprise as you pass through the gardens into the home. Uninterrupted, outstanding, beautiful view in every direction! The initial WOW is complimented by the fabulous decorations throughout the property. What a terrific venue to gather with family and friends and enjoy making memories together. Already developing our plans to return.
Daniel H.
Stayed 1 night in Mar 2019
10/10 Excellent
Davies H.
25 Feb 2019
Amazingly Beutiful
My crew of 13 unanimously decided that this striking cliff-top estate is The Best Property on all of St. Thomas. The panoramic, 270 degree Caribbean views are unequaled, the plush attention to detail in the architecture are fitting of a high-end vacation rental and the relaxing 'vibe' makes me long to return. As I type this review & look at the property picture, I can literally hear the wind whipping through these Palm Trees and I can feel my blood pressure drop as a feeling of content wells up inside me.