5 Windward
Discover the true essence of beachfront living in this newly remodeled exquisite two-bedroom condo, ideally situated in the prestigious Cowpet Bay West (a gated community), with Windward being the closest to the beach.
- Pool outdoor
- Hot tub
- Fire pit
-
Flexible check-in & out
Check-in after 4:00 PM • Check-out before 10:00 AM
-
Easy cancellation
You can cancel your trip for up to 14 days prior to start.
About this property
Discover the true essence of beachfront living in this newly remodeled exquisite two-bedroom condo, ideally situated in the prestigious Cowpet Bay West (a gated community), with Windward being the closest to the beach. Each bedroom is designed as a serene retreat, complete with its own en-suite bathroom, ensuring the ultimate comfort and privacy. Just a short, two-minute stroll takes you to the pristine sands of Cowpet Beach, where complimentary chaise lounges await, inviting you to relax and bask in the Caribbean sun. As a guest at 5 Windward, you’ll have exclusive access to the Elysian Pool and Hot Tub, perfect for a refreshing swim or a soothing soak after a day of island exploration. Dining options are just steps away, with the on-site Caribbean Fish Market and Sangrias offering delicious local cuisine right on the beach. When you're ready to explore further, the vibrant town of Red Hook is just a five-minute drive away. Here, you’ll find a variety of shopping, dining, and nightlife options, as well as the ferry to St. John, opening up even more possibilities for adventure! Expand your beach adventures with five additional beaches, each within approximately a mile of your doorstep, making 5 Windward your gateway to an unforgettable Caribbean experience. Whether you seek relaxation or excitement, this stunning condo offers the perfect blend of luxury, convenience, and island charm. Have questions? Just ask! I've been hosting short term rentals in St. Thomas for more than 15 years - so I will make sure we find you the best property to suit your specific needs, plus we have many fantastic options to choose from! Traveling with a larger group? Let us know and we will show you all the units nearby that are available for rental! Why book with Prestige Luxury Villas? 1- All of our properties undergo a 25-point inspection before arrival to ensure everything is in perfect order. 2- We stock every property with the basics, so you don’t have to sweat the small stuff! 3- The Prestige Luxury Villas team is made up of long-time Virgin Islands residents and passionate world travelers who love helping guests experience the best of the Caribbean. Every guest enjoys our complimentary full-service concierge—your insider guide to island adventures, hidden gems, and moments of pure relaxation. From the moment you book, we’re here to provide personalized recommendations and thoughtful trip-planning services tailored just for you. Whether you crave excitement or serenity, we’ll make sure your Caribbean getaway is everything you’ve been dreaming of! 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. **All credit card payments are subject to transaction processing fees. In the event of a reservation cancellation, these fees are non-refundable, as the constitute direct costs incurred during the payment transaction.
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Dec 12, 2025 | $350 | Not Available | 5 |
| Dec 13, 2025 | $350 | Not Available | 5 |
| Dec 14, 2025 | $350 | Not Available | 5 |
| Dec 15, 2025 | $350 | Not Available | 5 |
| Dec 16, 2025 | $350 | Not Available | 5 |
| Dec 17, 2025 | $350 | Not Available | 5 |
| Dec 18, 2025 | $350 | Not Available | 5 |
| Dec 19, 2025 | $350 | Not Available | 5 |
| Dec 20, 2025 | $350 | Not Available | 5 |
| Dec 21, 2025 | $350 | Not Available | 5 |
| Dec 22, 2025 | $350 | Not Available | 5 |
| Dec 23, 2025 | $350 | Not Available | 5 |
| Dec 24, 2025 | $350 | Not Available | 5 |
| Dec 25, 2025 | $350 | Not Available | 5 |
| Dec 26, 2025 | $350 | Not Available | 5 |
| Dec 27, 2025 | $350 | Not Available | 5 |
| Dec 28, 2025 | $350 | Not Available | 5 |
| Dec 29, 2025 | $350 | Not Available | 5 |
| Dec 30, 2025 | $350 | Not Available | 5 |
| Dec 31, 2025 | $350 | Not Available | 5 |
| Jan 1, 2026 | $350 | Not Available | 5 |
| Jan 2, 2026 | $350 | Not Available | 2 |
| Jan 3, 2026 | $350 | Not Available | 2 |
| Jan 4, 2026 | $350 | Not Available | 5 |
| Jan 5, 2026 | $350 | Not Available | 5 |
| Jan 6, 2026 | $350 | Not Available | 5 |
| Jan 7, 2026 | $350 | Not Available | 5 |
| Jan 8, 2026 | $350 | Not Available | 5 |
| Jan 9, 2026 | $350 | Not Available | 5 |
| Jan 10, 2026 | $350 | Not Available | 2 |
| Jan 11, 2026 | $350 | Not Available | 2 |
| Jan 12, 2026 | $350 | Not Available | 5 |
| Jan 13, 2026 | $350 | Not Available | 5 |
| Jan 14, 2026 | $350 | Not Available | 5 |
| Jan 15, 2026 | $350 | Not Available | 5 |
| Jan 16, 2026 | $350 | Not Available | 5 |
| Jan 17, 2026 | $350 | Not Available | 5 |
| Jan 18, 2026 | $350 | Not Available | 5 |
| Jan 19, 2026 | $350 | Not Available | 5 |
| Jan 20, 2026 | $350 | Not Available | 5 |
| Jan 21, 2026 | $350 | Not Available | 5 |
| Jan 22, 2026 | $350 | Not Available | 5 |
| Jan 23, 2026 | $350 | Available | 2 |
| Jan 24, 2026 | $350 | Available | 2 |
| Jan 25, 2026 | $350 | Not Available | 2 |
| Jan 26, 2026 | $350 | Not Available | 5 |
| Jan 27, 2026 | $350 | Not Available | 5 |
| Jan 28, 2026 | $350 | Not Available | 5 |
| Jan 29, 2026 | $350 | Not Available | 5 |
| Jan 30, 2026 | $350 | Not Available | 2 |
| Jan 31, 2026 | $350 | Not Available | 2 |
| Feb 1, 2026 | $350 | Not Available | 5 |
| Feb 2, 2026 | $350 | Not Available | 5 |
| Feb 3, 2026 | $350 | Not Available | 5 |
| Feb 4, 2026 | $350 | Not Available | 5 |
| Feb 5, 2026 | $350 | Not Available | 5 |
| Feb 6, 2026 | $350 | Available | 2 |
| Feb 7, 2026 | $350 | Available | 2 |
| Feb 8, 2026 | $350 | Not Available | 2 |
| Feb 9, 2026 | $350 | Not Available | 5 |
| Feb 10, 2026 | $350 | Not Available | 5 |
| Feb 11, 2026 | $350 | Available | 2 |
| Feb 12, 2026 | $350 | Available | 2 |
| Feb 13, 2026 | $350 | Not Available | 2 |
| Feb 14, 2026 | $350 | Not Available | 5 |
| Feb 15, 2026 | $350 | Not Available | 5 |
| Feb 16, 2026 | $350 | Not Available | 5 |
| Feb 17, 2026 | $350 | Not Available | 5 |
| Feb 18, 2026 | $350 | Not Available | 5 |
| Feb 19, 2026 | $350 | Not Available | 5 |
| Feb 20, 2026 | $350 | Not Available | 5 |
| Feb 21, 2026 | $350 | Not Available | 5 |
| Feb 22, 2026 | $350 | Not Available | 5 |
| Feb 23, 2026 | $350 | Not Available | 5 |
| Feb 24, 2026 | $350 | Not Available | 5 |
| Feb 25, 2026 | $350 | Not Available | 5 |
| Feb 26, 2026 | $350 | Available | 5 |
| Feb 27, 2026 | $350 | Available | 5 |
| Feb 28, 2026 | $350 | Available | 5 |
| Mar 1, 2026 | $350 | Available | 5 |
| Mar 2, 2026 | $350 | Available | 5 |
| Mar 3, 2026 | $350 | Available | 5 |
| Mar 4, 2026 | $350 | Available | 5 |
| Mar 5, 2026 | $350 | Available | 5 |
| Mar 6, 2026 | $350 | Not Available | 5 |
| Mar 7, 2026 | $350 | Not Available | 5 |
| Mar 8, 2026 | $350 | Not Available | 5 |
| Mar 9, 2026 | $350 | Not Available | 5 |
| Mar 10, 2026 | $350 | Not Available | 5 |
| Mar 11, 2026 | $350 | Not Available | 5 |
| Mar 12, 2026 | $350 | Not Available | 5 |
Top notch amenities
GUEST FAVORITES








Select dates in 5 Windward
Explore St. Thomas, St. Thomas
Things to know
Here are some things which you should know before booking 5 Windward