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Charlotte Amalie, US Virgin Islands

5 Windward

2 bedrooms4 beds2 baths6 guests

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.

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.

DatePrice (excl. fees and taxes)AvailabilityMin Stay (nights)
Nov 11, 2026$402Not Available5
Nov 12, 2026$390Not Available5
Nov 13, 2026$333Available3
Nov 14, 2026$393Not Available5
Nov 15, 2026$397Not Available5
Nov 16, 2026$399Not Available5
Nov 17, 2026$392Not Available5
Nov 18, 2026$394Not Available5
Nov 19, 2026$390Not Available5
Nov 20, 2026$336Available3
Nov 21, 2026$444Not Available5
Nov 22, 2026$444Not Available5
Nov 23, 2026$491Not Available7
Nov 24, 2026$494Not Available7
Nov 25, 2026$494Not Available7
Nov 26, 2026$494Not Available7
Nov 27, 2026$494Not Available7
Nov 28, 2026$455Not Available7
Nov 29, 2026$446Not Available7
Nov 30, 2026$447Not Available7
Dec 1, 2026$364Available3
Dec 2, 2026$373Available3
Dec 3, 2026$376Available3
Dec 4, 2026$444Not Available5
Dec 5, 2026$444Not Available5
Dec 6, 2026$444Not Available5
Dec 7, 2026$444Not Available5
Dec 8, 2026$444Not Available5
Dec 9, 2026$432Available3
Dec 10, 2026$444Available3
Dec 11, 2026$444Available3
Dec 12, 2026$444Not Available3
Dec 13, 2026$444Not Available3
Dec 14, 2026$444Not Available3
Dec 15, 2026$444Not Available3
Dec 16, 2026$444Not Available3
Dec 17, 2026$444Not Available3
Dec 18, 2026$444Available3
Dec 19, 2026$444Not Available3
Dec 20, 2026$542Not Available7
Dec 21, 2026$564Not Available7
Dec 22, 2026$564Not Available7
Dec 23, 2026$564Not Available7
Dec 24, 2026$564Not Available7
Dec 25, 2026$564Not Available7
Dec 26, 2026$564Available5
Dec 27, 2026$564Not Available7
Dec 28, 2026$564Not Available7
Dec 29, 2026$564Not Available7
Dec 30, 2026$564Not Available7
Dec 31, 2026$564Not Available7
Jan 1, 2027$534Not Available7
Jan 2, 2027$534Available3
Jan 3, 2027$534Available3
Jan 4, 2027$494Available3
Jan 5, 2027$494Not Available5
Jan 6, 2027$494Not Available5
Jan 7, 2027$494Not Available5
Jan 8, 2027$494Not Available5
Jan 9, 2027$494Not Available5
Jan 10, 2027$494Not Available5
Jan 11, 2027$494Not Available5
Jan 12, 2027$494Not Available5
Jan 13, 2027$494Not Available5
Jan 14, 2027$494Available2
Jan 15, 2027$494Available2
Jan 16, 2027$494Not Available5
Jan 17, 2027$494Not Available5
Jan 18, 2027$494Not Available5
Jan 19, 2027$494Not Available5
Jan 20, 2027$494Not Available5
Jan 21, 2027$494Not Available5
Jan 22, 2027$494Not Available5
Jan 23, 2027$494Not Available3
Jan 24, 2027$494Not Available3
Jan 25, 2027$494Not Available3
Jan 26, 2027$494Not Available3
Jan 27, 2027$494Not Available3
Jan 28, 2027$494Not Available3
Jan 29, 2027$494Not Available3
Jan 30, 2027$494Not Available3
Jan 31, 2027$494Not Available3
Feb 1, 2027$494Not Available3
Feb 2, 2027$494Not Available3
Feb 3, 2027$494Not Available3
Feb 4, 2027$494Not Available3
Feb 5, 2027$494Available2
Feb 6, 2027$494Available2
Feb 7, 2027$494Not Available5
Feb 8, 2027$494Not Available5
Feb 9, 2027$494Not Available5
Feb 10, 2027$494Not Available5
Feb 11, 2027$494Not Available5
Feb 12, 2027$494Not Available5
Feb 13, 2027$494Not Available3
Feb 14, 2027$494Not Available3
Feb 15, 2027$494Not Available3
Feb 16, 2027$494Not Available3
Feb 17, 2027$494Not Available3
Feb 18, 2027$494Not Available5
Feb 19, 2027$494Not Available5
Feb 20, 2027$494Not Available5
Feb 21, 2027$494Not Available5
Feb 22, 2027$494Not Available5
Feb 23, 2027$494Not Available5
Feb 24, 2027$494Not Available5
Feb 25, 2027$494Not Available5
Feb 26, 2027$494Not Available5
Feb 27, 2027$494Not Available5
Feb 28, 2027$494Not Available5
Mar 1, 2027$494Not Available5
Mar 2, 2027$494Not Available5
Mar 3, 2027$494Not Available5
Mar 4, 2027$494Not Available5
Mar 5, 2027$494Not Available5
Mar 6, 2027$494Not Available5
Mar 7, 2027$494Not Available5
Mar 8, 2027$494Not Available5
Mar 9, 2027$494Not Available5
Mar 10, 2027$494Not Available5
Mar 11, 2027$494Not Available2
Mar 12, 2027$494Not Available2
Mar 13, 2027$494Not Available5
Mar 14, 2027$494Not Available5
Mar 15, 2027$494Not Available5
Mar 16, 2027$494Not Available5
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Mar 20, 2027$494Not Available5
Mar 21, 2027$494Not Available5
Mar 22, 2027$494Not Available5
Mar 23, 2027$494Not Available5
Mar 24, 2027$494Not Available5
Mar 25, 2027$494Available3
Mar 26, 2027$494Not Available5
Mar 27, 2027$494Not Available5
Mar 28, 2027$494Not Available5
Mar 29, 2027$494Not Available5
Mar 30, 2027$494Not Available5
Mar 31, 2027$494Not Available5
Apr 1, 2027$494Not Available5
Apr 2, 2027$494Not Available5
Apr 3, 2027$494Not Available5
Apr 4, 2027$494Not Available3
Apr 5, 2027$494Not Available5
Apr 6, 2027$494Not Available5
Apr 7, 2027$494Not Available5
Apr 8, 2027$494Available2
Apr 9, 2027$494Available2
Apr 10, 2027$494Not Available5
Apr 11, 2027$494Not Available5
Apr 12, 2027$494Not Available5
Apr 13, 2027$494Not Available5
Apr 14, 2027$494Not Available5
Apr 15, 2027$494Not Available5
Apr 16, 2027$494Not Available5
Apr 17, 2027$494Not Available3
Apr 18, 2027$494Not Available3
Apr 19, 2027$494Not Available3
Apr 20, 2027$494Not Available3
Apr 21, 2027$494Not Available3
Apr 22, 2027$494Not Available3
Apr 23, 2027$494Not Available3
Apr 24, 2027$494Not Available5
Apr 25, 2027$494Not Available5
Apr 26, 2027$494Not Available5
Apr 27, 2027$494Not Available5
Apr 28, 2027$494Not Available5
Apr 29, 2027$494Not Available5
Apr 30, 2027$494Not Available5
May 1, 2027$494Available3
May 2, 2027$494Available3
May 3, 2027$494Available3
May 4, 2027$494Available3
May 5, 2027$494Available3
May 6, 2027$494Available3
May 7, 2027$494Available3
May 8, 2027$494Available3
May 9, 2027$494Available3
May 10, 2027$494Available3
May 11, 2027$494Available3
May 12, 2027$494Available5
May 13, 2027$494Available5
May 14, 2027$494Available5
May 15, 2027$494Available5
May 16, 2027$494Available5
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May 20, 2027$494Available5
May 21, 2027$494Available5
May 22, 2027$494Available5
May 23, 2027$494Available5
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May 25, 2027$494Available5
May 26, 2027$494Available5
May 27, 2027$494Available5
May 28, 2027$494Available5
May 29, 2027$494Available5
May 30, 2027$494Available5
May 31, 2027$494Available5
Jun 1, 2027$494Available5
Jun 2, 2027$494Available5
Jun 3, 2027$494Available5
Jun 4, 2027$494Available5
Jun 5, 2027$494Available5
Jun 6, 2027$494Available5
Jun 7, 2027$494Available5
Jun 8, 2027$494Available5
Jun 9, 2027$494Not Available5
Jun 10, 2027$494Not Available5
Jun 11, 2027$494Not Available5
Jun 12, 2027$494Not Available5
Jun 13, 2027$494Not Available5
Jun 14, 2027$494Not Available5
Jun 15, 2027$494Not Available5
Jun 16, 2027$494Available5
Jun 17, 2027$494Available5
Jun 18, 2027$494Available5
Jun 19, 2027$494Available5
Jun 20, 2027$494Available5
Jun 21, 2027$494Available5
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Jun 26, 2027$494Available5
Jun 27, 2027$494Available5
Jun 28, 2027$494Available5
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Jun 30, 2027$494Available5
Jul 1, 2027$494Available5
Jul 2, 2027$494Available5
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Jul 31, 2027$494Available5
Aug 1, 2027$444Available5
Aug 2, 2027$444Available5
Aug 3, 2027$444Available5
Aug 4, 2027$444Available5
Aug 5, 2027$444Available5
Aug 6, 2027$444Available5
Aug 7, 2027$444Not Available5
Aug 8, 2027$444Not Available5
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Aug 11, 2027$444Not Available5
Aug 12, 2027$444Not Available5
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Aug 14, 2027$444Available5
Aug 15, 2027$444Available5
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Aug 22, 2027$444Available5
Aug 23, 2027$444Available5
Aug 24, 2027$444Available5
Aug 25, 2027$441Available5
Aug 26, 2027$426Available5
Aug 27, 2027$444Available5
Aug 28, 2027$444Available5
Aug 29, 2027$443Available5
Aug 30, 2027$418Available5
Aug 31, 2027$409Available5
Sep 1, 2027$437Available5
Sep 2, 2027$443Available5
Sep 3, 2027$444Available5
Sep 4, 2027$444Available5
Sep 5, 2027$444Available5
Sep 6, 2027$444Available5
Sep 7, 2027$436Available5
Sep 8, 2027$435Available5
Sep 9, 2027$435Available5
Sep 10, 2027$420Available5
Sep 11, 2027$444Available5
Sep 12, 2027$438Available5
Sep 13, 2027$435Available5
Sep 14, 2027$435Available5
Sep 15, 2027$435Available5
Sep 16, 2027$435Available5
Sep 17, 2027$440Available5
Sep 18, 2027$444Available5
Sep 19, 2027$435Available5
Sep 20, 2027$435Available5
Sep 21, 2027$435Available5
Sep 22, 2027$435Available5
Sep 23, 2027$435Available5
Sep 24, 2027$432Available5
Sep 25, 2027$444Available5
Sep 26, 2027$444Available5
Sep 27, 2027$444Available5
Sep 28, 2027$444Available5
Sep 29, 2027$444Available5
Sep 30, 2027$444Available5
Oct 1, 2027$444Available5
Oct 2, 2027$444Available5
Oct 3, 2027$444Available5
Oct 4, 2027$444Available5
Oct 5, 2027$444Available5
Oct 6, 2027$444Available5
Oct 7, 2027$444Available5
Oct 8, 2027$444Available5
Oct 9, 2027$444Not Available5
Oct 10, 2027$444Not Available5
Oct 11, 2027$444Not Available5
Oct 12, 2027$444Not Available5
Oct 13, 2027$444Not Available5
Oct 14, 2027$444Not Available5
Oct 15, 2027$444Not Available5
Oct 16, 2027$444Available5
Oct 17, 2027$444Available5
Oct 18, 2027$444Available5
Oct 19, 2027$442Available5
Oct 20, 2027$444Available5
Oct 21, 2027$444Available5
Oct 22, 2027$444Available5
Oct 23, 2027$444Available5
Oct 24, 2027$444Available5
Oct 25, 2027$444Available5
Oct 26, 2027$444Available5
Oct 27, 2027$444Available5
Oct 28, 2027$444Available5
Oct 29, 2027$444Available5
Oct 30, 2027$444Available5
Oct 31, 2027$444Available5
Nov 1, 2027$444Available5
Nov 2, 2027$444Available5
Nov 3, 2027$444Available5
Nov 4, 2027$444Available5
Nov 5, 2027$444Available5
Nov 6, 2027$444Available5
Nov 7, 2027$444Available5
Nov 8, 2027$444Available5
Nov 9, 2027$444Available5
Nov 10, 2027$444Available5
Nov 11, 2027$444Available5
Nov 12, 2027$444Available5
Nov 13, 2027$444Available5
Nov 14, 2027$444Available5
Nov 15, 2027$444Available5
Nov 16, 2027$444Available5
Nov 17, 2027$444Available5
Nov 18, 2027$444Available5
Nov 19, 2027$444Available5
Nov 20, 2027$444Available5
Nov 21, 2027$444Available5
Nov 22, 2027$444Available5
Nov 23, 2027$494Available7
Nov 24, 2027$494Available7
Nov 25, 2027$494Available7
Nov 26, 2027$494Available7
Nov 27, 2027$494Available7
Nov 28, 2027$494Available7
Nov 29, 2027$494Available7
Nov 30, 2027$494Available7
Dec 1, 2027$444Available5
Dec 2, 2027$444Available5
Dec 3, 2027$444Available5
Dec 4, 2027$444Available5
Dec 5, 2027$444Available5
Dec 6, 2027$444Available5
Dec 7, 2027$444Available5
Dec 8, 2027$444Available5
Dec 9, 2027$444Available5
Dec 10, 2027$444Available5
Dec 11, 2027$444Available5
Dec 12, 2027$444Available5
Dec 13, 2027$444Available5
Dec 14, 2027$444Available5
Dec 15, 2027$444Available5
Dec 16, 2027$444Available5
Dec 17, 2027$444Available5
Dec 18, 2027$444Available5
Dec 19, 2027$444Available5
Dec 20, 2027$564Available7
Dec 21, 2027$564Available7
Dec 22, 2027$564Available7
Dec 23, 2027$564Available7
Dec 24, 2027$564Available7
Dec 25, 2027$564Available7
Dec 26, 2027$564Available7
Dec 27, 2027$564Not Available7
Dec 28, 2027$564Not Available7
Dec 29, 2027$564Not Available7
Dec 30, 2027$564Not Available7
Dec 31, 2027$564Not Available7
Jan 1, 2028$534Available7
Jan 2, 2028$534Available7
Jan 3, 2028$534Available7
Jan 4, 2028$494Available5
Jan 5, 2028$494Available5
Jan 6, 2028$494Available5
Jan 7, 2028$494Available5
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Jan 31, 2028$494Available5
Feb 1, 2028$494Available5
Feb 2, 2028$494Available5
Feb 3, 2028$494Not Available5
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May 14, 2028$494Available5

What this home offers

Beachfront
Waterfront
Ocean view
Beach access
Pool outdoor

What our guests say

4.98

51 reviews

N
Nichole
1 week ago

This place was beautiful he was very responsive and loved that he was helpful! Highly recommended!

J
Julia
1 week ago

Justin’s place was absolutely perfect! There were 4 of us on a girls trip and we had zero complaints! The condo is exactly as described and the views are breathtaking. Justin was great about communicating with us. The kitchen was well stocked and the beds were very comfortable. Easy walk to the beach and to two great restaurants. The access to the pool and hot tub were a nice addition. Can’t say enough positive things about our experience and we can’t wait to return!

S
Susan
October 2026

My husband and I had a wonderful stay at 5 Windward Way. The condo had everything needed for the stay. The beds and linens were extremely comfortable. The front porch which extended the whole width of the condo, had morning sun and afternoon shade… perfect for enjoying the spectacular views of Cowpet Bay. The onsite private beach, pool, beach bar and two restaurants were so convenient. We took a taxi wherever we needed to go. Justin was very responsive with any needs.

Where you’ll be

Charlotte Amalie, US Virgin Islands, 00802, US Virgin Islands

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Check-in & check-out

Check-in after 4:00 PM.

Check-out before 11:00 AM.

Property rules

Children welcome (2–12 years).

Infants welcome (under 2).

Maximum 6 guests.

No pets allowed.

No parties or events.

Cancellation policy

Add your trip dates to get the cancellation details for this stay.