Villa in Cruz Bay
8 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this villa rental
Tradewinds of Hart Bay – 4-Bedroom St. John Vacation Home with Private Pool & Panoramic Ocean Views
Welcome to Tradewinds of Hart Bay, a beautifully maintained 4-bedroom, 3.5-bath vacation home on St. John, USVI, offering spectacular ocean views, a private swimming pool, expansive wrap-around decks, and a peaceful location overlooking Hart Bay. Lovingly cared for and continually improved by its owners, Tradewinds provides a warm, comfortable island retreat where guests can relax, reconnect, and enjoy the natural beauty of St. John.
Perched high on the Bovocoap Peninsula, this spacious St. John vacation rental captures an impressive 260-degree panorama of the Caribbean, with views stretching across Hart Bay and the surrounding islands. From sunrise through sunset, the expansive decks provide a front-row seat to the ever-changing colors of the Caribbean sky.
Tradewinds combines four air-conditioned bedrooms, multiple indoor and outdoor living areas, a private pool, a fully equipped kitchen, and stunning ocean views, making it an excellent choice for families, couples, and groups of friends seeking a peaceful St. John getaway.
WHY YOU'LL LOVE TRADEWINDS OF HART BAY
- 4 bedrooms and 3.5 bathrooms
- Private swimming pool
- Panoramic 260-degree Caribbean Sea views
- Spectacular views overlooking Hart Bay
- Expansive wrap-around decks on two levels
- All four bedrooms feature air conditioning
- Two upper-level king master suites with private bathrooms
- Upper-level guest bedroom with two twins that convert to a king
- Main-level guest bedroom with queen bed
- Bright, open-concept great room
- Renovated kitchen with stainless steel appliances
- Indoor and outdoor dining
- Complimentary WiFi
- Flat-screen TV with Netflix, Hulu, and Sling TV
- Approximately 2 miles from Cruz Bay
- Peaceful location on the Bovocoap Peninsula
- Beautiful sunset views and ocean breezes
PERFECT FOR
Tradewinds of Hart Bay is ideal for travelers searching for a comfortable 4-bedroom St. John vacation rental with a private pool and ocean views.
The home is especially well suited for:
- Families needing flexible sleeping arrangements and multiple living spaces
- Couples traveling together who want two king master suites with private bathrooms
- Groups of friends looking for comfortable accommodations and shared indoor and outdoor spaces
- Beach and snorkeling enthusiasts who want easy access to St. John's bays and beaches
- Sun and sunset lovers who appreciate expansive outdoor decks and west-facing views
- Travelers seeking a peaceful location while remaining close to Cruz Bay
LOCATION – HART BAY & BOVOCOAP PENINSULA
Tradewinds is located on the scenic Bovocoap Peninsula overlooking Hart Bay on St. John. This peaceful residential setting offers privacy, spectacular views, and the soothing sound of waves breaking along the shoreline below. The villa's elevated position provides an exceptional 260-degree view of the Caribbean, allowing guests to enjoy both sunrise and sunset from the expansive decks.
The west-facing pool and sundeck are surrounded by lush tropical landscaping and provide a wonderful setting for relaxing throughout the day. Lounge in the sunshine, retreat beneath the awning for shade, or cool off with a refreshing swim while taking in the beautiful surroundings.
Despite its tranquil setting, Tradewinds is conveniently located only about 2 miles from Cruz Bay. Enjoy easy access to St. John's restaurants, shopping, galleries, nightlife, groceries, the ferry terminal, and island excursions before returning to the peaceful surroundings of Hart Bay.
LIVING & DINING
The bright and cheerful air-conditioned great room features an open floor plan that connects the kitchen, dining area, and living room, making it easy for everyone to gather together. Numerous screened sliding glass doors open to the expansive decks, allowing refreshing Caribbean breezes to flow through the home while bringing the spectacular ocean views indoors.
Comfortable furnishings create an inviting place to relax after a day exploring St. John. Enjoy the flat-screen TV with access to Netflix, Hulu, and Sling TV, or take advantage of complimentary WiFi.
Tradewinds offers several options for dining:
- Indoor dining table seating 6–8 guests
- Outdoor dining table for alfresco meals
- Kitchen bar for casual breakfasts and morning coffee
Whether you're enjoying a leisurely breakfast with an ocean view or gathering for dinner as the sun sets over Hart Bay, the home's indoor and outdoor spaces make dining part of the St. John experience.
KITCHEN
The renovated kitchen combines modern conveniences with everything needed to prepare meals during your island vacation. Stainless steel appliances include a refrigerator/freezer, electric stove, and dishwasher, along with ample cookware, dishes, utensils, and kitchen essentials.
The open layout allows the cook to remain connected with family and friends in the living and dining areas while enjoying the beautiful Caribbean views.
BEDROOMS & BATHROOMS
All four bedrooms at Tradewinds of Hart Bay are air conditioned and feature screened sliding glass doors that open onto the home's expansive wrap-around decks. Guests can wake up to beautiful Caribbean views and step outside to enjoy the fresh island air.
Lovango Cay Master Suite
Located on the upper level, the Lovango Cay Suite features a king-size bed, air conditioning, private en-suite bathroom, and access to the wrap-around deck with spectacular ocean views.
Waterlemon Cay Master Suite
The Waterlemon Cay Suite is also located upstairs and features a king-size bed, air conditioning, private en-suite bathroom, and access to the expansive deck. Wake up to panoramic Caribbean views and enjoy the peaceful surroundings of Hart Bay.
Francis Bay Guest Suite
The upper-level Francis Bay Suite offers two twin beds that can be converted into a king-size bed, making it a flexible sleeping option for families or friends traveling together. The room is air conditioned and opens to the wrap-around deck. The bedroom has access to the shared full bath located on the upper hallway.
Hawksnest Guest Suite
Located on the main living level, the Hawksnest Suite features a queen-size bed, air conditioning, and access to the home's outdoor deck. The bedroom has access to the 1/2 bath on the main level and the shared full bath on the upper level.
PRIVATE POOL & OUTDOOR LIVING
One of the highlights of Tradewinds is its private swimming pool and west-facing sundeck, surrounded by lush tropical gardens.
Spend the morning enjoying the sunshine on the expansive decks, cool off in the pool during the afternoon, or settle beneath the shaded awning with a good book. As the day winds down, gather outside to watch the sky transform into vibrant colors over the Caribbean.
The home's wrap-around decks extend across both levels, creating numerous places to relax and enjoy the spectacular views. No matter where you are, the Caribbean is always part of the experience.
A PEACEFUL ST. JOHN ESCAPE
Tradewinds of Hart Bay offers the perfect balance of privacy, comfort, spectacular views, and convenient access to Cruz Bay. From the moment you arrive, the home's welcoming atmosphere and beautiful tropical setting invite you to slow down and enjoy island life.
Listen to the gentle surf below, feel the Caribbean breeze across the decks, swim in your private pool, and watch unforgettable sunsets over Hart Bay.
For travelers searching for a 4-bedroom vacation rental on St. John with a private pool, panoramic ocean views, air-conditioned bedrooms, king master suites, and a location close to Cruz Bay, Tradewinds of Hart Bay is a wonderful choice for an unforgettable USVI vacation.
Welcome to Tradewinds of Hart Bay, a beautifully maintained 4-bedroom, 3.5-bath vacation home on St. John, USVI, offering spectacular ocean views, a private swimming pool, expansive wrap-around decks, and a peaceful location overlooking Hart Bay. Lovingly cared for and continually improved by its owners, Tradewinds provides a warm, comfortable island retreat where guests can relax, reconnect, and enjoy the natural beauty of St. John.
Perched high on the Bovocoap Peninsula, this spacious St. John vacation rental captures an impressive 260-degree panorama of the Caribbean, with views stretching across Hart Bay and the surrounding islands. From sunrise through sunset, the expansive decks provide a front-row seat to the ever-changing colors of the Caribbean sky.
Tradewinds combines four air-conditioned bedrooms, multiple indoor and outdoor living areas, a private pool, a fully equipped kitchen, and stunning ocean views, making it an excellent choice for families, couples, and groups of friends seeking a peaceful St. John getaway.
WHY YOU'LL LOVE TRADEWINDS OF HART BAY
- 4 bedrooms and 3.5 bathrooms
- Private swimming pool
- Panoramic 260-degree Caribbean Sea views
- Spectacular views overlooking Hart Bay
- Expansive wrap-around decks on two levels
- All four bedrooms feature air conditioning
- Two upper-level king master suites with private bathrooms
- Upper-level guest bedroom with two twins that convert to a king
- Main-level guest bedroom with queen bed
- Bright, open-concept great room
- Renovated kitchen with stainless steel appliances
- Indoor and outdoor dining
- Complimentary WiFi
- Flat-screen TV with Netflix, Hulu, and Sling TV
- Approximately 2 miles from Cruz Bay
- Peaceful location on the Bovocoap Peninsula
- Beautiful sunset views and ocean breezes
PERFECT FOR
Tradewinds of Hart Bay is ideal for travelers searching for a comfortable 4-bedroom St. John vacation rental with a private pool and ocean views.
The home is especially well suited for:
- Families needing flexible sleeping arrangements and multiple living spaces
- Couples traveling together who want two king master suites with private bathrooms
- Groups of friends looking for comfortable accommodations and shared indoor and outdoor spaces
- Beach and snorkeling enthusiasts who want easy access to St. John's bays and beaches
- Sun and sunset lovers who appreciate expansive outdoor decks and west-facing views
- Travelers seeking a peaceful location while remaining close to Cruz Bay
LOCATION – HART BAY & BOVOCOAP PENINSULA
Tradewinds is located on the scenic Bovocoap Peninsula overlooking Hart Bay on St. John. This peaceful residential setting offers privacy, spectacular views, and the soothing sound of waves breaking along the shoreline below. The villa's elevated position provides an exceptional 260-degree view of the Caribbean, allowing guests to enjoy both sunrise and sunset from the expansive decks.
The west-facing pool and sundeck are surrounded by lush tropical landscaping and provide a wonderful setting for relaxing throughout the day. Lounge in the sunshine, retreat beneath the awning for shade, or cool off with a refreshing swim while taking in the beautiful surroundings.
Despite its tranquil setting, Tradewinds is conveniently located only about 2 miles from Cruz Bay. Enjoy easy access to St. John's restaurants, shopping, galleries, nightlife, groceries, the ferry terminal, and island excursions before returning to the peaceful surroundings of Hart Bay.
LIVING & DINING
The bright and cheerful air-conditioned great room features an open floor plan that connects the kitchen, dining area, and living room, making it easy for everyone to gather together. Numerous screened sliding glass doors open to the expansive decks, allowing refreshing Caribbean breezes to flow through the home while bringing the spectacular ocean views indoors.
Comfortable furnishings create an inviting place to relax after a day exploring St. John. Enjoy the flat-screen TV with access to Netflix, Hulu, and Sling TV, or take advantage of complimentary WiFi.
Tradewinds offers several options for dining:
- Indoor dining table seating 6–8 guests
- Outdoor dining table for alfresco meals
- Kitchen bar for casual breakfasts and morning coffee
Whether you're enjoying a leisurely breakfast with an ocean view or gathering for dinner as the sun sets over Hart Bay, the home's indoor and outdoor spaces make dining part of the St. John experience.
KITCHEN
The renovated kitchen combines modern conveniences with everything needed to prepare meals during your island vacation. Stainless steel appliances include a refrigerator/freezer, electric stove, and dishwasher, along with ample cookware, dishes, utensils, and kitchen essentials.
The open layout allows the cook to remain connected with family and friends in the living and dining areas while enjoying the beautiful Caribbean views.
BEDROOMS & BATHROOMS
All four bedrooms at Tradewinds of Hart Bay are air conditioned and feature screened sliding glass doors that open onto the home's expansive wrap-around decks. Guests can wake up to beautiful Caribbean views and step outside to enjoy the fresh island air.
Lovango Cay Master Suite
Located on the upper level, the Lovango Cay Suite features a king-size bed, air conditioning, private en-suite bathroom, and access to the wrap-around deck with spectacular ocean views.
Waterlemon Cay Master Suite
The Waterlemon Cay Suite is also located upstairs and features a king-size bed, air conditioning, private en-suite bathroom, and access to the expansive deck. Wake up to panoramic Caribbean views and enjoy the peaceful surroundings of Hart Bay.
Francis Bay Guest Suite
The upper-level Francis Bay Suite offers two twin beds that can be converted into a king-size bed, making it a flexible sleeping option for families or friends traveling together. The room is air conditioned and opens to the wrap-around deck. The bedroom has access to the shared full bath located on the upper hallway.
Hawksnest Guest Suite
Located on the main living level, the Hawksnest Suite features a queen-size bed, air conditioning, and access to the home's outdoor deck. The bedroom has access to the 1/2 bath on the main level and the shared full bath on the upper level.
PRIVATE POOL & OUTDOOR LIVING
One of the highlights of Tradewinds is its private swimming pool and west-facing sundeck, surrounded by lush tropical gardens.
Spend the morning enjoying the sunshine on the expansive decks, cool off in the pool during the afternoon, or settle beneath the shaded awning with a good book. As the day winds down, gather outside to watch the sky transform into vibrant colors over the Caribbean.
The home's wrap-around decks extend across both levels, creating numerous places to relax and enjoy the spectacular views. No matter where you are, the Caribbean is always part of the experience.
A PEACEFUL ST. JOHN ESCAPE
Tradewinds of Hart Bay offers the perfect balance of privacy, comfort, spectacular views, and convenient access to Cruz Bay. From the moment you arrive, the home's welcoming atmosphere and beautiful tropical setting invite you to slow down and enjoy island life.
Listen to the gentle surf below, feel the Caribbean breeze across the decks, swim in your private pool, and watch unforgettable sunsets over Hart Bay.
For travelers searching for a 4-bedroom vacation rental on St. John with a private pool, panoramic ocean views, air-conditioned bedrooms, king master suites, and a location close to Cruz Bay, Tradewinds of Hart Bay is a wonderful choice for an unforgettable USVI vacation.
Amenities
Non-smoking
No pets allowed
Map of Cruz Bay
Ratings and reviews
10 / 10Outstanding·Jun 2026
Accurate description of property. Clean with of plenty towels and cutlery. Extraordinary views from both porches. Almost always a breeze to keep the insects away.
10 / 10Outstanding·Apr 2026
Tradewinds of Hart Bay is a stunning property, and the hosts thought of every detail. It surpassed all our expectations—amazing views, great location, and the property itself was beautiful. Communication was great with the management team. We would love to return.
10 / 10Outstanding·Jul 2025
I was a little worried because of only 2 Vrbo reviews, but it was perfect for our group. We brought our 18 & 20 yo sons and their girlfriends. The views are fantastic, the sofa is super comfy and large! There are games, a nicely stocked kitchen and all supplies needed for the beach. We had issue within water, I called and a plumber was to the house in 30 minutes and resolved problem. Great customer service. We have stayed in lots of VRBO’s - this one is a good one!
10 / 10Outstanding·Jul 2025
This is a well appointed home with a spacious and comfortable main living area. We were pleasantly surprised by how well the kitchen was stocked and truly pleased to see that they had a medium number of small children's toys. Shade around the pool is wonderful. We had one small issue when we first checked in and received excellent customer service/communication by the property manager and they fully resolved the issue within 3 hours. Accidents/mistakes happen, great customer service is intentional and much appreciated. Easy to recommend this home and Carribean Villas of St John.
$$$$
Top rated by guests
10Outstanding
(7 Ratings)
"Accurate description of property. Clean with of plenty towels and cutlery. Extraordinary views from both porches. Almost always a breeze to keep the insects away."
Jonathan T.Don't miss out! Price and availability may change
