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.

  • Ocean view
  • Pool outdoor
  • Hot tub
6 guests
2 bedrooms
2 bathrooms
1000 sqft
  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 11:00 AM

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

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Mar 27, 2026$455Not Available3
Mar 28, 2026$438Available3
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$469Not Available2
Apr 7, 2026$407Available3
Apr 8, 2026$439Not Available3
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$394Available3
Apr 25, 2026$494Not Available5
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$421Available3
May 3, 2026$494Not Available3
May 4, 2026$466Not Available3
May 5, 2026$439Not Available3
May 6, 2026$394Available3
May 7, 2026$394Available3
May 8, 2026$394Available3
May 9, 2026$494Not Available7
May 10, 2026$494Not Available7
May 11, 2026$483Not Available7
May 12, 2026$460Not Available7
May 13, 2026$472Not Available7
May 14, 2026$479Not Available7
May 15, 2026$492Not Available7
May 16, 2026$394Available3
May 17, 2026$394Available3
May 18, 2026$394Available3
May 19, 2026$394Available3
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$494Available3
Jun 22, 2026$431Not Available3
Jun 23, 2026$434Not Available3
Jun 24, 2026$481Not Available3
Jun 25, 2026$465Not Available3

Where you'll sleep

Amenities

GUEST FAVORITES

Ocean view
Pool outdoor
Hot tub
Fire pit
Fire place
BBQ Area
Patio
Balcony
Outdoor dining area

Where you'll be

Discover the vibrant allure of St. Thomas, where Caribbean beauty meets exhilarating adventure. Indulge in exquisite dining steps away at Sunset Grille at Secret Harbour, or embark on an underwater journey a short drive away at Coral World Ocean Park. Explore the island's charm with easy access to Mongoose Junction for unique shopping and the Skyride to Paradise Point for breathtaking views, or take a short drive to the Cruz Bay Ferry Dock for island hopping.

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 11:00 AM
6 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval