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. 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.