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!
** There are extra guest fees after 4 guests.
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.
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!
** There are extra guest fees after 4 guests.
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.
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!
** There are extra guest fees after 4 guests.
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
For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jul 16, 2026 | $394 | Available | 3 |
| Jul 17, 2026 | $432 | Not Available | 3 |
| Jul 18, 2026 | $446 | Not Available | 3 |
| Jul 19, 2026 | $442 | Not Available | 3 |
| Jul 20, 2026 | $494 | Not Available | 3 |
| Jul 21, 2026 | $494 | Not Available | 3 |
| Jul 22, 2026 | $494 | Not Available | 3 |
| Jul 23, 2026 | $494 | Not Available | 3 |
| Jul 24, 2026 | $494 | Not Available | 3 |
| Jul 25, 2026 | $477 | Not Available | 3 |
| Jul 26, 2026 | $474 | Not Available | 3 |
| Jul 27, 2026 | $433 | Not Available | 3 |
| Jul 28, 2026 | $422 | Not Available | 3 |
| Jul 29, 2026 | $484 | Not Available | 3 |
| Jul 30, 2026 | $485 | Not Available | 3 |
| Jul 31, 2026 | $397 | Not Available | 3 |
| Aug 1, 2026 | $444 | Not Available | 3 |
| Aug 2, 2026 | $444 | Not Available | 3 |
| Aug 3, 2026 | $444 | Not Available | 3 |
| Aug 4, 2026 | $444 | Not Available | 3 |
| Aug 5, 2026 | $444 | Not Available | 3 |
| Aug 6, 2026 | $444 | Not Available | 3 |
| Aug 7, 2026 | $444 | Not Available | 3 |
| Aug 8, 2026 | $444 | Not Available | 3 |
| Aug 9, 2026 | $428 | Not Available | 5 |
| Aug 10, 2026 | $407 | Not Available | 5 |
| Aug 11, 2026 | $411 | Not Available | 5 |
| Aug 12, 2026 | $399 | Not Available | 5 |
| Aug 13, 2026 | $403 | Not Available | 5 |
| Aug 14, 2026 | $404 | Not Available | 5 |
| Aug 15, 2026 | $392 | Not Available | 5 |
| Aug 16, 2026 | $388 | Not Available | 3 |
| Aug 17, 2026 | $372 | Not Available | 3 |
| Aug 18, 2026 | $385 | Not Available | 3 |
| Aug 19, 2026 | $351 | Not Available | 3 |
| Aug 20, 2026 | $361 | Not Available | 3 |
| Aug 21, 2026 | $374 | Not Available | 3 |
| Aug 22, 2026 | $349 | Available | 3 |
| Aug 23, 2026 | $333 | Available | 3 |
| Aug 24, 2026 | $333 | Available | 3 |
| Aug 25, 2026 | $359 | Not Available | 3 |
| Aug 26, 2026 | $340 | Not Available | 3 |
| Aug 27, 2026 | $338 | Not Available | 3 |
| Aug 28, 2026 | $333 | Not Available | 3 |
| Aug 29, 2026 | $333 | Not Available | 3 |
| Aug 30, 2026 | $333 | Not Available | 3 |
| Aug 31, 2026 | $333 | Not Available | 3 |
| Sep 1, 2026 | $333 | Not Available | 3 |
| Sep 2, 2026 | $333 | Not Available | 3 |
| Sep 3, 2026 | $333 | Not Available | 3 |
| Sep 4, 2026 | $333 | Available | 3 |
| Sep 5, 2026 | $333 | Available | 3 |
| Sep 6, 2026 | $333 | Available | 3 |
| Sep 7, 2026 | $333 | Available | 3 |
| Sep 8, 2026 | $333 | Not Available | 3 |
| Sep 9, 2026 | $333 | Not Available | 3 |
| Sep 10, 2026 | $333 | Not Available | 3 |
| Sep 11, 2026 | $333 | Not Available | 3 |
| Sep 12, 2026 | $338 | Not Available | 3 |
| Sep 13, 2026 | $333 | Not Available | 3 |
| Sep 14, 2026 | $333 | Not Available | 3 |
| Sep 15, 2026 | $333 | Not Available | 3 |
| Sep 16, 2026 | $333 | Not Available | 3 |
| Sep 17, 2026 | $333 | Not Available | 3 |
| Sep 18, 2026 | $333 | Not Available | 3 |
| Sep 19, 2026 | $333 | Not Available | 3 |
| Sep 20, 2026 | $333 | Not Available | 3 |
| Sep 21, 2026 | $333 | Not Available | 3 |
| Sep 22, 2026 | $333 | Not Available | 3 |
| Sep 23, 2026 | $333 | Not Available | 3 |
| Sep 24, 2026 | $333 | Not Available | 3 |
| Sep 25, 2026 | $333 | Not Available | 3 |
| Sep 26, 2026 | $335 | Not Available | 3 |
| Sep 27, 2026 | $333 | Not Available | 3 |
| Sep 28, 2026 | $333 | Not Available | 3 |
| Sep 29, 2026 | $333 | Not Available | 3 |
| Sep 30, 2026 | $333 | Not Available | 3 |
| Oct 1, 2026 | $333 | Not Available | 3 |
| Oct 2, 2026 | $333 | Not Available | 3 |
| Oct 3, 2026 | $333 | Not Available | 5 |
| Oct 4, 2026 | $336 | Not Available | 5 |
| Oct 5, 2026 | $346 | Not Available | 5 |
| Oct 6, 2026 | $347 | Not Available | 5 |
| Oct 7, 2026 | $348 | Not Available | 5 |
| Oct 8, 2026 | $355 | Not Available | 5 |
| Oct 9, 2026 | $397 | Not Available | 5 |
| Oct 10, 2026 | $421 | Not Available | 3 |
| Oct 11, 2026 | $421 | Not Available | 3 |
| Oct 12, 2026 | $392 | Not Available | 3 |
| Oct 13, 2026 | $407 | Not Available | 3 |
| Oct 14, 2026 | $402 | Not Available | 3 |
Amenities
5.0 · 46 reviews
The place was exactly as described. Loved the beach towels and chairs as we traveled to other beaches. The 3 different sized coolers made travel to other beaches easy. Our beach was quiet and serene. Pool and hot tub were spacious. Easy to get a drink at the bar. Justin sent a ton of helpful information before arrival and was responsive during trip. Would highly recommend for anyone searching for a quiet beach destination with easy access to activities throughout the island.
First time on the island with my wife and 2 kids and couldn’t have asked for a better place to stay. We have stayed at a few Airbnb all over and this was easily the most well appointed, comfortable and best experience. Justin was very responsive and easy to communicate with during the stay. The location was literally perfect with beach and pool access and the place had everything you needed for a great trip. I couldn’t recommend enough and would 100% stay here again.
Justin was great to work with and the view from the Condo was even better than the pictures. It was fun to watch all the boating activity in the mornings/evenings while relaxing in the light ocean breeze. At no fault of the host, there were several times throughout stay that electricity to the whole complex went0 out. I believe this issue goes beyond the complex and impacts the wider area. While somewhat annoying, generally, it was ok, only lasting a minute or two. There was electricity line work actively happening during our trip so will probably be fixed soon and wouldn't let it prevent a future stay.
Where you'll be
St. Thomas, St. Thomas, 00802, VI
Our promise to you
Lower prices, every time
Direct line, real care
Not just a transaction
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.