St. Thomas, St. Thomas

5 Windward

2 bedrooms 4 beds 2 baths 6 guests New

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.

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

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) AvailabilityMin Stay (nights)
May 18, 2026$394Not Available3
May 19, 2026$394Not Available3
May 20, 2026$394Not Available3
May 21, 2026$394Not Available3
May 22, 2026$410Not Available3
May 23, 2026$419Not Available3
May 24, 2026$480Not Available3
May 25, 2026$494Not Available3
May 26, 2026$469Not Available3
May 27, 2026$454Not Available5
May 28, 2026$456Not Available5
May 29, 2026$470Not Available5
May 30, 2026$490Not Available5
May 31, 2026$494Not Available7
Jun 1, 2026$494Not Available7
Jun 2, 2026$494Not Available7
Jun 3, 2026$494Not Available7
Jun 4, 2026$494Not Available7
Jun 5, 2026$494Not Available7
Jun 6, 2026$494Not Available7
Jun 7, 2026$492Not Available5
Jun 8, 2026$494Not Available5
Jun 9, 2026$453Not Available5
Jun 10, 2026$475Not Available5
Jun 11, 2026$471Not Available5
Jun 12, 2026$494Not Available5
Jun 13, 2026$494Not Available5
Jun 14, 2026$494Not Available3
Jun 15, 2026$494Not Available3
Jun 16, 2026$494Not Available3
Jun 17, 2026$494Not Available3
Jun 18, 2026$494Not Available3
Jun 19, 2026$494Not Available3
Jun 20, 2026$494Not Available3
Jun 21, 2026$449Available3
Jun 22, 2026$431Not Available3
Jun 23, 2026$434Not Available3
Jun 24, 2026$481Not Available3
Jun 25, 2026$465Not Available3
Jun 26, 2026$484Not Available3
Jun 27, 2026$485Not Available3
Jun 28, 2026$394Available3
Jun 29, 2026$394Available3
Jun 30, 2026$394Available3
Jul 1, 2026$414Available3
Jul 2, 2026$479Not Available3
Jul 3, 2026$494Not Available3
Jul 4, 2026$490Not Available3
Jul 5, 2026$447Not Available3
Jul 6, 2026$420Available3
Jul 7, 2026$453Not Available3
Jul 8, 2026$464Not Available3
Jul 9, 2026$479Not Available3
Jul 10, 2026$484Not Available3
Jul 11, 2026$482Not Available3
Jul 12, 2026$462Not Available3
Jul 13, 2026$420Available3
Jul 14, 2026$398Available3
Jul 15, 2026$398Available3
Jul 16, 2026$419Available3
Jul 17, 2026$432Available3
Jul 18, 2026$446Available3
Jul 19, 2026$442Available3
Jul 20, 2026$494Not Available3
Jul 21, 2026$494Not Available3
Jul 22, 2026$494Not Available3
Jul 23, 2026$494Not Available3
Jul 24, 2026$494Not Available3
Jul 25, 2026$477Not Available3
Jul 26, 2026$474Not Available3
Jul 27, 2026$433Not Available3
Jul 28, 2026$422Not Available3
Jul 29, 2026$484Not Available3
Jul 30, 2026$485Not Available3
Jul 31, 2026$420Available3
Aug 1, 2026$444Not Available3
Aug 2, 2026$444Not Available3
Aug 3, 2026$444Not Available3
Aug 4, 2026$444Not Available3
Aug 5, 2026$444Not Available3
Aug 6, 2026$444Not Available3
Aug 7, 2026$444Not Available3
Aug 8, 2026$444Not Available3
Aug 9, 2026$428Not Available5
Aug 10, 2026$407Not Available5
Aug 11, 2026$411Not Available5
Aug 12, 2026$399Not Available5
Aug 13, 2026$403Not Available5
Aug 14, 2026$404Not Available5
Aug 15, 2026$392Not Available5
Aug 16, 2026$388Not Available3

Where you'll sleep

Amenities

Beachfront
Waterfront
Ocean view
Beach access
Pool outdoor
Hot tub
Patio
Balcony

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Where you'll be

St. Thomas, St. Thomas, 00802, VI

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 11:00 AM.
Maximum 6 guests.