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.
- Ocean view
- Pool outdoor
- Hot tub
-
Flexible check-in & out
Check-in after 4:00 PM • Check-out before 11:00 AM
About the 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) |
|---|---|---|---|
| Mar 27, 2026 | $455 | Not Available | 3 |
| Mar 28, 2026 | $438 | Available | 3 |
| Mar 29, 2026 | $494 | Not Available | 5 |
| Mar 30, 2026 | $494 | Not Available | 5 |
| Mar 31, 2026 | $494 | Not Available | 5 |
| Apr 1, 2026 | $494 | Not Available | 5 |
| Apr 2, 2026 | $494 | Not Available | 5 |
| Apr 3, 2026 | $494 | Not Available | 5 |
| Apr 4, 2026 | $494 | Not Available | 5 |
| Apr 5, 2026 | $494 | Not Available | 5 |
| Apr 6, 2026 | $469 | Not Available | 2 |
| Apr 7, 2026 | $407 | Available | 3 |
| Apr 8, 2026 | $439 | Not Available | 3 |
| Apr 9, 2026 | $418 | Not Available | 3 |
| Apr 10, 2026 | $423 | Not Available | 3 |
| Apr 11, 2026 | $396 | Not Available | 3 |
| Apr 12, 2026 | $397 | Not Available | 3 |
| Apr 13, 2026 | $417 | Not Available | 3 |
| Apr 14, 2026 | $394 | Available | 3 |
| Apr 15, 2026 | $394 | Available | 3 |
| Apr 16, 2026 | $394 | Available | 3 |
| Apr 17, 2026 | $394 | Available | 3 |
| Apr 18, 2026 | $395 | Not Available | 3 |
| Apr 19, 2026 | $415 | Not Available | 3 |
| Apr 20, 2026 | $406 | Not Available | 3 |
| Apr 21, 2026 | $436 | Not Available | 3 |
| Apr 22, 2026 | $422 | Not Available | 3 |
| Apr 23, 2026 | $435 | Not Available | 3 |
| Apr 24, 2026 | $394 | Available | 3 |
| Apr 25, 2026 | $494 | Not Available | 5 |
| Apr 26, 2026 | $494 | Not Available | 5 |
| Apr 27, 2026 | $461 | Not Available | 5 |
| Apr 28, 2026 | $442 | Not Available | 5 |
| Apr 29, 2026 | $461 | Not Available | 5 |
| Apr 30, 2026 | $474 | Not Available | 5 |
| May 1, 2026 | $494 | Not Available | 5 |
| May 2, 2026 | $421 | Available | 3 |
| May 3, 2026 | $494 | Not Available | 3 |
| May 4, 2026 | $466 | Not Available | 3 |
| May 5, 2026 | $439 | Not Available | 3 |
| May 6, 2026 | $394 | Available | 3 |
| May 7, 2026 | $394 | Available | 3 |
| May 8, 2026 | $394 | Available | 3 |
| May 9, 2026 | $494 | Not Available | 7 |
| May 10, 2026 | $494 | Not Available | 7 |
| May 11, 2026 | $483 | Not Available | 7 |
| May 12, 2026 | $460 | Not Available | 7 |
| May 13, 2026 | $472 | Not Available | 7 |
| May 14, 2026 | $479 | Not Available | 7 |
| May 15, 2026 | $492 | Not Available | 7 |
| May 16, 2026 | $394 | Available | 3 |
| May 17, 2026 | $394 | Available | 3 |
| May 18, 2026 | $394 | Available | 3 |
| May 19, 2026 | $394 | Available | 3 |
| May 20, 2026 | $394 | Not Available | 3 |
| May 21, 2026 | $394 | Not Available | 3 |
| May 22, 2026 | $410 | Not Available | 3 |
| May 23, 2026 | $419 | Not Available | 3 |
| May 24, 2026 | $480 | Not Available | 3 |
| May 25, 2026 | $494 | Not Available | 3 |
| May 26, 2026 | $469 | Not Available | 3 |
| May 27, 2026 | $454 | Not Available | 5 |
| May 28, 2026 | $456 | Not Available | 5 |
| May 29, 2026 | $470 | Not Available | 5 |
| May 30, 2026 | $490 | Not Available | 5 |
| May 31, 2026 | $494 | Not Available | 7 |
| Jun 1, 2026 | $494 | Not Available | 7 |
| Jun 2, 2026 | $494 | Not Available | 7 |
| Jun 3, 2026 | $494 | Not Available | 7 |
| Jun 4, 2026 | $494 | Not Available | 7 |
| Jun 5, 2026 | $494 | Not Available | 7 |
| Jun 6, 2026 | $494 | Not Available | 7 |
| Jun 7, 2026 | $492 | Not Available | 5 |
| Jun 8, 2026 | $494 | Not Available | 5 |
| Jun 9, 2026 | $453 | Not Available | 5 |
| Jun 10, 2026 | $475 | Not Available | 5 |
| Jun 11, 2026 | $471 | Not Available | 5 |
| Jun 12, 2026 | $494 | Not Available | 5 |
| Jun 13, 2026 | $494 | Not Available | 5 |
| Jun 14, 2026 | $494 | Not Available | 3 |
| Jun 15, 2026 | $494 | Not Available | 3 |
| Jun 16, 2026 | $494 | Not Available | 3 |
| Jun 17, 2026 | $494 | Not Available | 3 |
| Jun 18, 2026 | $494 | Not Available | 3 |
| Jun 19, 2026 | $494 | Not Available | 3 |
| Jun 20, 2026 | $494 | Not Available | 3 |
| Jun 21, 2026 | $494 | Available | 3 |
| Jun 22, 2026 | $431 | Not Available | 3 |
| Jun 23, 2026 | $434 | Not Available | 3 |
| Jun 24, 2026 | $481 | Not Available | 3 |
| Jun 25, 2026 | $465 | Not Available | 3 |
Amenities
GUEST FAVORITES









Where you'll be
Things to know
Here are some things which you should know before booking 5 Windward