Operated by a Wander partner
Trusted operators, vetted by Wander
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 villa's 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.
** There are extra guest fees beyond 12 guests.
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.
Travelers who cancel at least 60 days before check-in will get back 100% of the amount they've paid, less any/all 3rd party transaction or processing fees where applicable. Cancellations made between 30 and 60 days prior to beginning of rental forfeit the 50% deposit made at the time of the booking, less any/all 3rd party transaction or processing fees wherever applicable. Cancellations made less than 30 days prior to beginning of stay forfeit the total amount due for the duration of the stay.
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!
Bedroom 1
1 king bed, 1 full sofa
Bedroom 2
1 king bed, 1 full sofa
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Bedroom 1
1 king bed, 1 full sofa
Bedroom 2
1 king bed, 1 full sofa
Bedroom 3
1 king bed
Bedroom 4
1 king bed
Bedroom 5
1 king bed
St. Thomas, St. Thomas 00802, VI
St. Thomas, St. Thomas, VIThe Longboard offers vibrant Caribbean-inspired seafood and shareable small plates crafted with fresh, local ingredients, paired with creative cocktails in a laid-back island atmosphere perfect for relaxing and savoring tropical flavors.
Tarpon's Table offers fresh, locally caught seafood in a relaxed waterfront setting with covered outdoor seating overlooking the marina, creating a welcoming island dining experience. The friendly staff and flavorful dishes like lobster and poke bowls make it a standout spot in St. Thomas.
PRIME at Paradise Point is a premier steakhouse in St. Thomas featuring prime-grade beef, fresh Caribbean seafood, and exotic meats like wagyu and bison, all served with stunning sunset views over Charlotte Amalie harbor and complemented by handcrafted cocktails and an intimate, romantic ambiance.
Sun & Sea Bar & Grill offers a relaxed waterfront dining experience with fresh, locally sourced seafood and vibrant island flavors, complemented by stunning ocean views and lively local music. It’s the perfect spot to savor casual coastal dishes in a welcoming, family-friendly atmosphere.
Sunset Grille at Secret Harbour is a beachfront Caribbean restaurant nestled steps from the water's edge, offering Latin Caribbean cuisine with global influences in a magical sunset ambiance. Perfect for both casual and fine dining, it combines exceptional seafood and creative dishes with impeccable service and breathtaking ocean views.
High Tide is a lively waterfront spot serving fresh seafood, juicy steaks, and tasty burgers in a fun, nautical setting with great views and a tiki bar vibe.
Bolongo Bay Beach Resort offers a vibrant Caribbean dining experience with fresh, made-to-order meals served poolside or oceanfront, complemented by tropical cocktails, live island music, and stunning sea views in a lively, three-story open-air setting.
Duffy's Love Shack is a lively, quirky tiki bar in a parking lot in Red Hook, famous for its tropical cocktails, fun atmosphere, and flavorful Caribbean-inspired bar food like conch fritters and jerk chicken nachos. It's the perfect spot for casual dining and vibrant nights with live music.
The Beach Bar offers a vibrant beachfront dining experience with refreshing cocktails, live entertainment, and a laid-back atmosphere perfect for enjoying sun, sand, and great food right by the water. Whether you want to relax or stay active with beach games, it’s the ultimate spot for fun and flavor.
Hook'd USVI offers vibrant American Caribbean cuisine featuring fresh seafood like mahi and pork belly tacos, all enjoyed in a lively waterfront setting overlooking the marina with friendly service and weekend live music. A perfect spot for flavorful meals and a relaxed island vibe.
Drake's Seat offers breathtaking panoramic views of Magens Bay and the surrounding Virgin Islands from a historic lookout once linked to Sir Francis Drake. It's perfect for history buffs, photographers, and anyone seeking a stunning Caribbean sunset.
Charlotte Amalie Overlook offers stunning panoramic views of Charlotte Amalie, its bustling harbor, and nearby islands, making it a perfect spot for photographers, nature lovers, and anyone seeking a peaceful escape with breathtaking Caribbean scenery.
The Pirates Treasure Museum offers an immersive adventure into the Golden Age of Piracy with rare artifacts, interactive exhibits, and hands-on pirate activities, perfect for history buffs and families seeking a thrilling, educational experience. Dive into pirate legends and shipwreck treasures in a fun, engaging setting.
The 99 Steps in Charlotte Amalie offer a charming climb through history with their unique Danish brickwork and vibrant tropical surroundings, perfect for history buffs and photographers seeking stunning views and a taste of island heritage.
The Cruz Bay Visitor Center is the perfect starting point for exploring Virgin Islands National Park, offering expert guidance, maps, and exhibits that help hikers, snorkelers, and nature lovers discover the island’s stunning trails, beaches, and rich history. Ideal for outdoor adventurers and families alike.
Bolongo Bay Beach Resort offers a vibrant Caribbean escape with endless water sports, lively beach bars, and unforgettable snorkeling adventures, perfect for travelers seeking both relaxation and active island fun. Ideal for families, couples, and friends who love sun, sea, and local culture.
The Skyride to Paradise Point offers a smooth, scenic tram ride 700 feet above St. Thomas, delivering breathtaking panoramic views of the harbor, island, and ocean. Perfect for travelers who enjoy stunning vistas, relaxing dining, and iconic tropical drinks in a vibrant, friendly atmosphere.
Coral World Ocean Park offers unforgettable marine encounters like walking underwater with a Sea Trek helmet, swimming with dolphins and sea lions, and exploring vibrant aquariums and nature trails. It’s perfect for families and anyone passionate about ocean life and adventure.
Fort Christian is a vibrant historical landmark in Charlotte Amalie, offering visitors a unique glimpse into over 300 years of Caribbean colonial life, from Danish military defense to a governor’s residence and prison. History buffs and culture lovers will enjoy exploring its striking red walls and rich stories of pirates, governors, and island heritage.
Free cancellation up to 14 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events allowed
Check-in after 4:00 pm
Check-out before 11:00 am
14 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 21, 2026 | $2450 | Not Available |
| Jul 22, 2026 | $2450 | Not Available |
| Jul 23, 2026 | $2450 | Not Available |
| Jul 24, 2026 | $2394 | Not Available |
| Jul 25, 2026 | $2100 | Available |
| Jul 26, 2026 | $2100 | Available |
| Jul 27, 2026 | $2100 | Available |
| Jul 28, 2026 | $2100 | Available |
| Jul 29, 2026 | $2100 | Available |
| Jul 30, 2026 | $2100 | Available |
| Jul 31, 2026 | $2100 | Available |
| Aug 1, 2026 | $2000 | Available |
| Aug 2, 2026 | $2102 | Not Available |
| Aug 3, 2026 | $2050 | Not Available |
| Aug 4, 2026 | $2000 | Not Available |
| Aug 5, 2026 | $2000 | Not Available |
| Aug 6, 2026 | $2027 | Not Available |
| Aug 7, 2026 | $2039 | Not Available |
| Aug 8, 2026 | $2000 | Not Available |
| Aug 9, 2026 | $2000 | Available |
| Aug 10, 2026 | $2000 | Available |
| Aug 11, 2026 | $2000 | Available |
| Aug 12, 2026 | $2000 | Available |
| Aug 13, 2026 | $2000 | Available |
| Aug 14, 2026 | $2000 | Available |
| Aug 15, 2026 | $2000 | Available |
| Aug 16, 2026 | $2000 | Available |
| Aug 17, 2026 | $2000 | Available |
| Aug 18, 2026 | $2000 | Available |
| Aug 19, 2026 | $2000 | Available |
| Aug 20, 2026 | $2000 | Available |
| Aug 21, 2026 | $2000 | Available |
| Aug 22, 2026 | $2000 | Available |
| Aug 23, 2026 | $2000 | Available |
| Aug 24, 2026 | $2000 | Available |
| Aug 25, 2026 | $2000 | Available |
| Aug 26, 2026 | $2000 | Available |
| Aug 27, 2026 | $2000 | Available |
| Aug 28, 2026 | $2000 | Available |
| Aug 29, 2026 | $2000 | Available |
| Aug 30, 2026 | $2000 | Available |
| Aug 31, 2026 | $2000 | Available |
| Sep 1, 2026 | $2000 | Available |
| Sep 2, 2026 | $2000 | Available |
| Sep 3, 2026 | $2000 | Available |
| Sep 4, 2026 | $2000 | Available |
| Sep 5, 2026 | $2000 | Available |
| Sep 6, 2026 | $2000 | Available |
| Sep 7, 2026 | $2000 | Available |
| Sep 8, 2026 | $2000 | Available |
| Sep 9, 2026 | $2000 | Available |
| Sep 10, 2026 | $2000 | Available |
| Sep 11, 2026 | $2000 | Available |
| Sep 12, 2026 | $2000 | Available |
| Sep 13, 2026 | $2000 | Available |
| Sep 14, 2026 | $2000 | Available |
| Sep 15, 2026 | $2000 | Available |
| Sep 16, 2026 | $2000 | Available |
| Sep 17, 2026 | $2000 | Available |
| Sep 18, 2026 | $2000 | Available |
| Sep 19, 2026 | $2000 | Available |
| Sep 20, 2026 | $2000 | Available |
| Sep 21, 2026 | $2000 | Available |
| Sep 22, 2026 | $2000 | Available |
| Sep 23, 2026 | $2000 | Available |
| Sep 24, 2026 | $2000 | Available |
| Sep 25, 2026 | $2000 | Available |
| Sep 26, 2026 | $2000 | Available |
| Sep 27, 2026 | $2000 | Available |
| Sep 28, 2026 | $2000 | Available |
| Sep 29, 2026 | $2000 | Available |
| Sep 30, 2026 | $2000 | Available |
| Oct 1, 2026 | $2000 | Available |
| Oct 2, 2026 | $2000 | Available |
| Oct 3, 2026 | $2000 | Available |
| Oct 4, 2026 | $2000 | Available |
| Oct 5, 2026 | $2000 | Available |
| Oct 6, 2026 | $2000 | Available |
| Oct 7, 2026 | $2000 | Available |
| Oct 8, 2026 | $2000 | Available |
| Oct 9, 2026 | $2000 | Available |
| Oct 10, 2026 | $2300 | Available |
| Oct 11, 2026 | $2070 | Available |
| Oct 12, 2026 | $2030 | Available |
| Oct 13, 2026 | $2029 | Available |
| Oct 14, 2026 | $2010 | Available |
| Oct 15, 2026 | $2000 | Available |
| Oct 16, 2026 | $2000 | Available |
| Oct 17, 2026 | $2000 | Available |
| Oct 18, 2026 | $2000 | Available |
| Oct 19, 2026 | $2000 | Available |