St. Thomas, St. Thomas

5 Windward

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6 guests
2 bedrooms
2 bathrooms
1000 sqft

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
6 guests
2 bedrooms
2 bathrooms
1000 sqft

  • 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.

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) AvailabilityMin Stay (nights)
Dec 12, 2025$350Not Available5
Dec 13, 2025$350Not Available5
Dec 14, 2025$350Not Available5
Dec 15, 2025$350Not Available5
Dec 16, 2025$350Not Available5
Dec 17, 2025$350Not Available5
Dec 18, 2025$350Not Available5
Dec 19, 2025$350Not Available5
Dec 20, 2025$350Not Available5
Dec 21, 2025$350Not Available5
Dec 22, 2025$350Not Available5
Dec 23, 2025$350Not Available5
Dec 24, 2025$350Not Available5
Dec 25, 2025$350Not Available5
Dec 26, 2025$350Not Available5
Dec 27, 2025$350Not Available5
Dec 28, 2025$350Not Available5
Dec 29, 2025$350Not Available5
Dec 30, 2025$350Not Available5
Dec 31, 2025$350Not Available5
Jan 1, 2026$350Not Available5
Jan 2, 2026$350Not Available2
Jan 3, 2026$350Not Available2
Jan 4, 2026$350Not Available5
Jan 5, 2026$350Not Available5
Jan 6, 2026$350Not Available5
Jan 7, 2026$350Not Available5
Jan 8, 2026$350Not Available5
Jan 9, 2026$350Not Available5
Jan 10, 2026$350Not Available2
Jan 11, 2026$350Not Available2
Jan 12, 2026$350Not Available5
Jan 13, 2026$350Not Available5
Jan 14, 2026$350Not Available5
Jan 15, 2026$350Not Available5
Jan 16, 2026$350Not Available5
Jan 17, 2026$350Not Available5
Jan 18, 2026$350Not Available5
Jan 19, 2026$350Not Available5
Jan 20, 2026$350Not Available5
Jan 21, 2026$350Not Available5
Jan 22, 2026$350Not Available5
Jan 23, 2026$350Available2
Jan 24, 2026$350Available2
Jan 25, 2026$350Not Available2
Jan 26, 2026$350Not Available5
Jan 27, 2026$350Not Available5
Jan 28, 2026$350Not Available5
Jan 29, 2026$350Not Available5
Jan 30, 2026$350Not Available2
Jan 31, 2026$350Not Available2
Feb 1, 2026$350Not Available5
Feb 2, 2026$350Not Available5
Feb 3, 2026$350Not Available5
Feb 4, 2026$350Not Available5
Feb 5, 2026$350Not Available5
Feb 6, 2026$350Available2
Feb 7, 2026$350Available2
Feb 8, 2026$350Not Available2
Feb 9, 2026$350Not Available5
Feb 10, 2026$350Not Available5
Feb 11, 2026$350Available2
Feb 12, 2026$350Available2
Feb 13, 2026$350Not Available2
Feb 14, 2026$350Not Available5
Feb 15, 2026$350Not Available5
Feb 16, 2026$350Not Available5
Feb 17, 2026$350Not Available5
Feb 18, 2026$350Not Available5
Feb 19, 2026$350Not Available5
Feb 20, 2026$350Not Available5
Feb 21, 2026$350Not Available5
Feb 22, 2026$350Not Available5
Feb 23, 2026$350Not Available5
Feb 24, 2026$350Not Available5
Feb 25, 2026$350Not Available5
Feb 26, 2026$350Available5
Feb 27, 2026$350Available5
Feb 28, 2026$350Available5
Mar 1, 2026$350Available5
Mar 2, 2026$350Available5
Mar 3, 2026$350Available5
Mar 4, 2026$350Available5
Mar 5, 2026$350Available5
Mar 6, 2026$350Not Available5
Mar 7, 2026$350Not Available5
Mar 8, 2026$350Not Available5
Mar 9, 2026$350Not Available5
Mar 10, 2026$350Not Available5
Mar 11, 2026$350Not Available5
Mar 12, 2026$350Not Available5

Top notch amenities

GUEST FAVORITES

Pool outdoor
Hot tub
Fire pit
Fire place
BBQ Area
Patio
Balcony
Bay views
Gazebo

Where you'll sleep



Explore St. Thomas, St. Thomas

Discover St. Thomas’s vibrant coastal charm, where pristine beaches meet captivating attractions. Indulge in exquisite dining at Sunset Grille at Secret Harbour, steps away, or explore the underwater world at Coral World Ocean Park, a short drive from your doorstep. For panoramic island vistas, the Skyride to Paradise Point is within easy reach, while a quick drive also takes you to Mongoose Junction for unique shopping and the Cruz Bay Ferry Dock for island hopping adventures.

Things to know

Here are some things which you should know before booking 5 Windward

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
6 guests maximum
Pets not allowed
Events require approval

Cancellation policy

This property follows Tom Fallenstein St Thomas’s standard cancellation policy.