# 5 Windward – 2 Bedroom Vacation Rental in St. Thomas, St. Thomas | Tom Fallenstein St Thomas

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.

**Property URL**: https://tom-fallenstein-st-thomas.wanderos.com/property/608719099761001923/5-windward
**Markdown URL**: https://tom-fallenstein-st-thomas.wanderos.com/property/608719099761001923/5-windward.md

## Property Overview
- **Sleeps**: 6 guests
- **Bedrooms**: 2 bedrooms
- **Bathrooms**: 2
- **Square Footage**: 1,000 sq ft


## Pricing & Availability
- **Nightly Rate**: $402 - $494 (before taxes and fees)
- **Next Available**: June 21, 2026
- **Available Days**: 11 days in the next 90 days
- **Daily Pricing (Next 90 Days)**:
  - May 19, 2026: $394 (Not Available) (3 night min)
  - May 20, 2026: $394 (Not Available) (3 night min)
  - May 21, 2026: $394 (Not Available) (3 night min)
  - May 22, 2026: $410 (Not Available) (3 night min)
  - May 23, 2026: $419 (Not Available) (3 night min)
  - May 24, 2026: $480 (Not Available) (3 night min)
  - May 25, 2026: $494 (Not Available) (3 night min)
  - May 26, 2026: $469 (Not Available) (3 night min)
  - May 27, 2026: $454 (Not Available) (5 night min)
  - May 28, 2026: $456 (Not Available) (5 night min)
  - May 29, 2026: $470 (Not Available) (5 night min)
  - May 30, 2026: $490 (Not Available) (5 night min)
  - May 31, 2026: $494 (Not Available) (7 night min)
  - Jun 1, 2026: $494 (Not Available) (7 night min)
  - Jun 2, 2026: $494 (Not Available) (7 night min)
  - Jun 3, 2026: $494 (Not Available) (7 night min)
  - Jun 4, 2026: $494 (Not Available) (7 night min)
  - Jun 5, 2026: $494 (Not Available) (7 night min)
  - Jun 6, 2026: $494 (Not Available) (7 night min)
  - Jun 7, 2026: $492 (Not Available) (5 night min)
  - Jun 8, 2026: $494 (Not Available) (5 night min)
  - Jun 9, 2026: $453 (Not Available) (5 night min)
  - Jun 10, 2026: $475 (Not Available) (5 night min)
  - Jun 11, 2026: $471 (Not Available) (5 night min)
  - Jun 12, 2026: $494 (Not Available) (5 night min)
  - Jun 13, 2026: $494 (Not Available) (5 night min)
  - Jun 14, 2026: $494 (Not Available) (3 night min)
  - Jun 15, 2026: $494 (Not Available) (3 night min)
  - Jun 16, 2026: $494 (Not Available) (3 night min)
  - Jun 17, 2026: $494 (Not Available) (3 night min)
  - Jun 18, 2026: $494 (Not Available) (3 night min)
  - Jun 19, 2026: $494 (Not Available) (3 night min)
  - Jun 20, 2026: $494 (Not Available) (3 night min)
  - Jun 21, 2026: $494 (Available) (3 night min)
  - Jun 22, 2026: $431 (Not Available) (3 night min)
  - Jun 23, 2026: $434 (Not Available) (3 night min)
  - Jun 24, 2026: $481 (Not Available) (3 night min)
  - Jun 25, 2026: $465 (Not Available) (3 night min)
  - Jun 26, 2026: $484 (Not Available) (3 night min)
  - Jun 27, 2026: $485 (Not Available) (3 night min)
  - Jun 28, 2026: $409 (Available) (3 night min)
  - Jun 29, 2026: $402 (Available) (3 night min)
  - Jun 30, 2026: $404 (Available) (3 night min)
  - Jul 1, 2026: $421 (Available) (3 night min)
  - Jul 2, 2026: $479 (Not Available) (3 night min)
  - Jul 3, 2026: $494 (Not Available) (3 night min)
  - Jul 4, 2026: $490 (Not Available) (3 night min)
  - Jul 5, 2026: $447 (Not Available) (3 night min)
  - Jul 6, 2026: $412 (Available) (3 night min)
  - Jul 7, 2026: $453 (Not Available) (3 night min)
  - Jul 8, 2026: $464 (Not Available) (3 night min)
  - Jul 9, 2026: $479 (Not Available) (3 night min)
  - Jul 10, 2026: $484 (Not Available) (3 night min)
  - Jul 11, 2026: $482 (Not Available) (3 night min)
  - Jul 12, 2026: $462 (Not Available) (3 night min)
  - Jul 13, 2026: $435 (Available) (3 night min)
  - Jul 14, 2026: $406 (Available) (3 night min)
  - Jul 15, 2026: $416 (Available) (3 night min)
  - Jul 16, 2026: $420 (Available) (3 night min)
  - Jul 17, 2026: $436 (Not Available) (3 night min)
  - Jul 18, 2026: $451 (Not Available) (3 night min)
  - Jul 19, 2026: $460 (Not Available) (3 night min)
  - Jul 20, 2026: $494 (Not Available) (3 night min)
  - Jul 21, 2026: $494 (Not Available) (3 night min)
  - Jul 22, 2026: $494 (Not Available) (3 night min)
  - Jul 23, 2026: $494 (Not Available) (3 night min)
  - Jul 24, 2026: $494 (Not Available) (3 night min)
  - Jul 25, 2026: $477 (Not Available) (3 night min)
  - Jul 26, 2026: $474 (Not Available) (3 night min)
  - Jul 27, 2026: $433 (Not Available) (3 night min)
  - Jul 28, 2026: $422 (Not Available) (3 night min)
  - Jul 29, 2026: $484 (Not Available) (3 night min)
  - Jul 30, 2026: $485 (Not Available) (3 night min)
  - Jul 31, 2026: $468 (Available) (3 night min)
  - Aug 1, 2026: $444 (Not Available) (3 night min)
  - Aug 2, 2026: $444 (Not Available) (3 night min)
  - Aug 3, 2026: $444 (Not Available) (3 night min)
  - Aug 4, 2026: $444 (Not Available) (3 night min)
  - Aug 5, 2026: $444 (Not Available) (3 night min)
  - Aug 6, 2026: $444 (Not Available) (3 night min)
  - Aug 7, 2026: $444 (Not Available) (3 night min)
  - Aug 8, 2026: $444 (Not Available) (3 night min)
  - Aug 9, 2026: $428 (Not Available) (5 night min)
  - Aug 10, 2026: $407 (Not Available) (5 night min)
  - Aug 11, 2026: $411 (Not Available) (5 night min)
  - Aug 12, 2026: $399 (Not Available) (5 night min)
  - Aug 13, 2026: $403 (Not Available) (5 night min)
  - Aug 14, 2026: $404 (Not Available) (5 night min)
  - Aug 15, 2026: $392 (Not Available) (5 night min)
  - Aug 16, 2026: $388 (Not Available) (3 night min)
  - Aug 17, 2026: $372 (Not Available) (3 night min)


## Availability Rules 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 listed minimum stay, and no intervening nights are marked "Not Available".
- Prices are nightly rates before taxes and fees. Final checkout pricing may include taxes, fees, add-ons, discounts, and payment terms.
- If a requested date range extends beyond the 90-day table, visit the property URL for live booking details.

## Stay Timing
- **Check-in**: After 4:00 PM
- **Check-out**: Before 11:00 AM

## Location
- **Address**: St. Thomas, St. Thomas, Virgin Islands (U.S.)
- **Postal Code**: 00802
- **Coordinates**: 18.31656902, -64.84581068
- **Local Area**: Beautiful destination with local attractions

## Sleeping Arrangements
### Bedroom 1
KING BED, TWIN BED

### Bedroom 2
KING BED, TWIN BED

## Amenities
- BEACHFRONT
- WATERFRONT
- OCEAN_VIEW
- BEACH_ACCESS
- POOL_OUTDOOR
- HOT_TUB
- PATIO
- BALCONY
- BAY_VIEWS
- SMOKE_DETECTOR
- FIRST_AID_KIT
- AIR_CONDITIONING
- DRYER
- HOT_WATER
- WASHER
- TV
- KITCHEN
- HAIR_DRYER
- IRON
- DISHWASHER
- COFFEE_MAKER
- CARBON_MONOXIDE_DETECTOR
- BED_LINENS
- HANGERS
- COMMUNITY_POOL
- IRONING_BOARD
- BBQ_UTENSILS
- TOASTER
- MICROWAVE
- OVEN
- STOVE
- FRIDGE
- BATH_LINENS
- GARDEN
- DISHES
- COOKING_BASICS
- BLACKOUT_CURTAINS
- MASSAGE_TABLE
- BOAT
- TOYS
- DINING_TABLE
- ICE_MAKER
- SPICES
- KAYAKS
- LUGGAGE_DROP_OFF_ALLOWED
- LONG_TERM_STAYS_ALLOWED
- BEDROOM_DOOR_LOCK
- FISHING_AREA
- HIKE_TRAIL_NEARBY
- DEDICATED_WORKSPACE
- PAID_PARKING
- PRIVATE_CHEF
- BUTLER
- MAID
- CLEANING_SUPPLIES
- BODY_SOAP
- CEILING_FAN
- BAKING_SHEET
- BLENDER
- FREEZER
- WIFI
- WINE_GLASSES
- FREE_PARKING
- FIRE_EXTINGUISHER
- OCEAN_VIEW
- POOL_OUTDOOR
- HOT_TUB
- OUTDOOR_SEATING
- GAZEBO
- WATERFALL
- FIRE_PIT
- BBQ_AREA
- PATIO
- BBQ_UTENSILS
- OUTDOOR_SEATING
- OUTDOOR_DINING_AREA
- GARDEN
- FIRE_PIT
- BBQ_AREA
- BALCONY
- OUTDOOR_SEATING
- OUTDOOR_DINING_AREA
- BBQ_UTENSILS
- BAY_VIEWS
- FIRE_PLACE
- BALCONY
- AIR_CONDITIONING
- HEATING
- CEILING_FAN
- TV
- OUTDOOR_SEATING
- KITCHEN
- DISHWASHER
- MICROWAVE
- OVEN
- COFFEE_MAKER
- FRIDGE
- COOKING_BASICS
- STOVE
- FREEZER
- DISHES
- COFFEE
- KETTLE
- TEA
- SPICES
- SILVERWARE
- CLEANING_SUPPLIES
- WINE_GLASSES
- AIR_CONDITIONING
- HANGERS
- BED_LINENS
- TV
- DESK
- DAY_BED
- AIR_CONDITIONING
- ENSUITE_BATHROOM
- BALCONY
- CRIB
- BED_LINENS
- AIR_CONDITIONING
- TV
- OUTDOOR_SEATING
- ENSUITE_BATHROOM
- HAIR_DRYER
- SHAMPOO
- ENSUITE_BATHROOM
- BATH_LINENS
- TOILET
- SHOWER
- SHOWER_GEL
- CONDITIONER
- BODY_SOAP
- SHOWER
- ENSUITE_BATHROOM
- BATH_LINENS
- TOILET
- SHOWER_GEL
- SHAMPOO
- CONDITIONER
- BODY_SOAP
- DEDICATED_WORKSPACE
- DESK
- TV
- SURFBOARDS
- POOL_TOYS
- WASHER
- DRYER
- IRON
- CLEANING_SUPPLIES

## Reviews
This property has 46 reviews with an average rating of 10.0/5.

### Recent Reviews
- **Kathleen Rousseau**: "The place was exactly as described. Loved the beach towels and chairs as we traveled to other beaches. The 3 different sized coolers made travel to other beaches easy. 

Our beach was quiet and serene. Pool and hot tub were spacious. Easy to get a drink at the bar. 

Justin sent a ton of helpful information before arrival and was responsive during trip. 

Would highly recommend for anyone searching for a quiet beach destination with easy access to activities throughout the island." (10/5)
- **Justin Billig**: "First time on the island with my wife and 2 kids and couldn’t have asked for a better place to stay. We have stayed at a few Airbnb all over and this was easily the most well appointed, comfortable and best experience. Justin was very responsive and easy to communicate with during the stay. The location was literally perfect with beach and pool access and the place had everything you needed for a great trip. I couldn’t recommend enough and would 100% stay here again." (10/5)
- **Rob Moyer**: "Justin was great to work with and the view from the Condo was even better than the pictures.  It was fun to watch all the boating activity in the mornings/evenings while relaxing in the light ocean breeze.  At no fault of the host, there were several times throughout stay that electricity to the whole complex went0 out.  I believe this issue goes beyond the complex and impacts the wider area.  While somewhat annoying, generally, it was ok, only lasting a minute or two. There was electricity line work actively happening during our trip so will probably be fixed soon and wouldn't let it prevent a future stay." (10/5)

## Guest Services
- **24/7 Concierge**: Available through the Tom Fallenstein St Thomas app
- **Housekeeping**: Professional cleaning service
- **Maintenance**: On-call support for any issues
- **Local Recommendations**: Dining, activities, and experiences

## Property Details
- **Property ID**: 608719099761001923
- **Property Slug**: 5-windward

## Booking Information
For more information and to book this property, visit:
https://tom-fallenstein-st-thomas.wanderos.com/property/608719099761001923/5-windward

Or contact Tom Fallenstein St Thomas customer service for assistance.

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*Last modified: 2026-05-19*
*This markdown file is generated automatically for AI agents and search engines.*