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 is a lively Huntington Beach staple offering a New American menu with standout seafood and steak dishes, a full bar, and a vibrant sports-friendly atmosphere in a historic setting. Its friendly staff and multiple patios make it a local favorite for casual dining and game day gatherings.
The Beach Bar offers a vibrant beachfront experience with refreshing tropical cocktails, island-style grilled favorites, and lively entertainment, perfect for relaxing by the sea or enjoying stunning sunsets. Its spacious decks and fun beach games create a laid-back, energetic atmosphere.
Bolongo Bay Beach Resort offers a vibrant Caribbean dining experience with made-to-order meals, tropical cocktails, and stunning ocean views in a lively, three-story outdoor restaurant setting by the pool. Enjoy fresh island flavors and live music in a relaxed, beachside atmosphere.
Hook’d USVI offers a vibrant American Caribbean dining experience with fresh seafood and flavorful dishes in a relaxed waterfront setting overlooking the marina, complemented by friendly service and live music. It’s a perfect spot for breakfast, lunch, or dinner in St. Thomas.
Tarpon's Table offers fresh, locally caught seafood in a relaxed dockside setting with beautiful marina views, creating a warm and inviting island dining experience. The friendly staff and flavorful dishes like lobster and poke bowls make every visit memorable.
Sun & Sea Bar & Grill offers a casual waterfront dining experience featuring fresh, locally sourced seafood and vibrant island flavors, all set against stunning ocean views with live music and a welcoming, family-friendly atmosphere. Perfect for savoring fresh catch dishes and local craft drinks by the sea.
Prime at Paradise Point offers an exceptional steakhouse experience with prime cuts, fresh local seafood, and handcrafted cocktails, all set against breathtaking panoramic views of St. Thomas and stunning Caribbean sunsets. Its intimate ambiance and impeccable service make every visit memorable.
High Tide offers a relaxed beachside vibe with fresh, locally inspired seafood and island dishes, perfect for enjoying Caribbean sunsets and crafted cocktails just steps from the ferry dock. Its friendly, down-to-earth atmosphere makes every meal feel like a vacation.
Sunset Grille at Secret Harbour offers vibrant Latin Caribbean cuisine just steps from the beach, paired with stunning ocean views and a relaxed, inviting atmosphere perfect for any occasion.
Duffy's Love Shack is a lively tiki bar in a St. Thomas parking lot, famous for its wild tropical cocktails, casual Caribbean-inspired bar food, and fun, energetic atmosphere with live music and quirky charm. It's a must-visit spot for a laid-back, vibrant island experience.
Coral World Ocean Park offers unforgettable marine encounters where you can swim with dolphins and sea lions, snorkel with sharks, and explore vibrant aquariums and underwater observatories. It’s perfect for families and marine life enthusiasts seeking hands-on ocean adventures.
Bolongo Bay Beach Resort offers a vibrant Caribbean escape with endless water sports, lively live music, and a welcoming atmosphere perfect for families, friends, and couples seeking adventure or relaxation by the sea. Enjoy unique experiences like the Snorkel Booze Hunt and sailing adventures in a cozy, all-inclusive setting.
Experience a thrilling tram ride 700 feet above sea level to Paradise Point, where panoramic views of St. Thomas Harbor, cruise ships, and distant islands await. Perfect for sightseers, photographers, and anyone who loves stunning vistas paired with delicious tropical drinks and local shops.
Climb the historic 99 Steps in St. Thomas to enjoy a unique blend of colonial history, vibrant tropical flowers, and stunning views of Charlotte Amalie—perfect for history buffs, photographers, and curious travelers seeking a memorable island experience.
The Cruz Bay Visitor Center is the perfect starting point for exploring Virgin Islands National Park, offering expert guidance on hiking, snorkeling, and local history. Nature lovers and adventure seekers will enjoy planning their island adventures here with helpful rangers and informative exhibits.
The Pirates Treasure Museum offers an immersive adventure with interactive exhibits, authentic shipwreck treasures, and thrilling hurricane simulators, perfect for history buffs and families eager to explore pirate legends and deep-sea discoveries.
Charlotte Amalie Overlook offers stunning panoramic views of the harbor, city, and nearby islands, making it perfect for sightseeing, photography, and soaking in Caribbean beauty. It’s ideal for travelers who enjoy scenic vistas and peaceful moments above St. Thomas.
Drake's Seat offers a stunning panoramic view of Magens Bay and the Virgin Islands, blending rich history with breathtaking scenery. Ideal for history buffs, photographers, and anyone seeking a peaceful spot to soak in the Caribbean’s natural beauty.
Fort Christian is a captivating 17th-century Danish fortress in Charlotte Amalie, perfect for history enthusiasts eager to explore Caribbean colonial life, architecture, and tales of pirates, governors, and settlers within its thick, red walls.
Contact your host to cancel your reservation.
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 |