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)
Feb 6, 2026$394Available2
Feb 7, 2026$394Available2
Feb 8, 2026$494Not Available2
Feb 9, 2026$494Not Available3
Feb 10, 2026$494Not Available3
Feb 11, 2026$441Not Available2
Feb 12, 2026$490Not Available2
Feb 13, 2026$494Not Available7
Feb 14, 2026$494Not Available7
Feb 15, 2026$494Not Available7
Feb 16, 2026$494Not Available7
Feb 17, 2026$494Not Available7
Feb 18, 2026$494Not Available7
Feb 19, 2026$494Not Available7
Feb 20, 2026$494Not Available7
Feb 21, 2026$494Not Available7
Feb 22, 2026$494Not Available7
Feb 23, 2026$494Not Available3
Feb 24, 2026$494Not Available3
Feb 25, 2026$494Not Available3
Feb 26, 2026$494Not Available2
Feb 27, 2026$494Not Available3
Feb 28, 2026$494Not Available3
Mar 1, 2026$494Not Available3
Mar 2, 2026$494Not Available3
Mar 3, 2026$494Not Available3
Mar 4, 2026$494Not Available3
Mar 5, 2026$494Not Available3
Mar 6, 2026$494Not Available5
Mar 7, 2026$494Not Available5
Mar 8, 2026$494Not Available5
Mar 9, 2026$494Not Available5
Mar 10, 2026$494Not Available5
Mar 11, 2026$494Not Available5
Mar 12, 2026$494Not Available5
Mar 13, 2026$494Not Available5
Mar 14, 2026$482Not Available2
Mar 15, 2026$494Not Available2
Mar 16, 2026$494Not Available5
Mar 17, 2026$494Not Available5
Mar 18, 2026$494Not Available5
Mar 19, 2026$494Not Available5
Mar 20, 2026$494Not Available5
Mar 21, 2026$494Not Available5
Mar 22, 2026$494Not Available5
Mar 23, 2026$493Not Available2
Mar 24, 2026$444Not Available2
Mar 25, 2026$443Not Available3
Mar 26, 2026$449Not Available3
Mar 27, 2026$494Not Available5
Mar 28, 2026$494Not Available5
Mar 29, 2026$494Not Available5
Mar 30, 2026$494Not Available5
Mar 31, 2026$494Not Available5
Apr 1, 2026$494Not Available5
Apr 2, 2026$494Not Available5
Apr 3, 2026$494Not Available5
Apr 4, 2026$494Not Available5
Apr 5, 2026$494Not Available5
Apr 6, 2026$494Available2
Apr 7, 2026$494Available2
Apr 8, 2026$439Not Available2
Apr 9, 2026$418Not Available3
Apr 10, 2026$423Not Available3
Apr 11, 2026$396Not Available3
Apr 12, 2026$397Not Available3
Apr 13, 2026$417Not Available3
Apr 14, 2026$394Available3
Apr 15, 2026$394Available3
Apr 16, 2026$394Available3
Apr 17, 2026$394Available3
Apr 18, 2026$395Not Available3
Apr 19, 2026$415Not Available3
Apr 20, 2026$406Not Available3
Apr 21, 2026$436Not Available3
Apr 22, 2026$422Not Available3
Apr 23, 2026$435Not Available3
Apr 24, 2026$426Not Available2
Apr 25, 2026$494Not Available2
Apr 26, 2026$494Not Available5
Apr 27, 2026$461Not Available5
Apr 28, 2026$442Not Available5
Apr 29, 2026$461Not Available5
Apr 30, 2026$474Not Available5
May 1, 2026$494Not Available5
May 2, 2026$467Not Available2
May 3, 2026$494Not Available2
May 4, 2026$466Not Available3
May 5, 2026$439Not Available3
May 6, 2026$394Available3
May 7, 2026$394Available3

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.