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Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views

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A covered outdoor dining area with wicker furniture, a pool, and tropical vegetation. - Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views (St John)
A two-story house with a large pool, surrounded by lush greenery and a view of the ocean. - Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views (St John)
A swimming pool with lounge chairs and a view of the ocean. - Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views (St John)
A spacious living area with a dining set, a staircase, and large windows offering a view of greenery and a balcony. - Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views (St John)
A dining area with a wooden table set for six, surrounded by wicker chairs. A spiral staircase is visible in the background, leading to an upper level. - Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views (St John)
Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views provides amenities, such as a garden and laundry facilities. Active travellers can enjoy kayaking at this villa. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

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About this property

Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views

  • Tradewinds of Hart Bay – 4-Bedroom St. John Holiday Home with Private Pool & Panoramic Ocean Views

    Welcome to Tradewinds of Hart Bay, a beautifully maintained 4-bedroom, 3.5-bath holiday 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 holiday 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 colours 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 travellers searching for a comfortable 4-bedroom St. John holiday 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 travelling together who want two king master suites with private bathrooms
    - Groups of friends looking for comfortable accommodation and shared indoor and outdoor spaces
    - Beach and snorkelling 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
    - Travellers 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 holiday. 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 travelling 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 colours 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 travellers searching for a 4-bedroom holiday 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 holiday.

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About the area

Located in St. John, this villa is in the mountains and near the beach. Blackbeard's Castle is a notable landmark, and the area's natural beauty can be seen at Virgin Islands National Park and Cruz Bay Beach. Kayaking, scuba diving and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails nearby. Visit our St. John travel guide
View more Villas in St. John
Map
St John, VI

What's nearby

  • Devers Bay
    1 min walk - 0.1 miles
  • Rendezvous Bay
    1 min walk - 0.1 miles
  • Chocolate Hole
    4 min walk - 0.3 miles
  • Sunset Beach
    4 min walk - 0.3 miles
  • Chocolate Hole Beach
    8 min walk - 0.5 miles

Getting around

  • St. Thomas (SPB-St. Thomas Seaplane Base)
    64 min drive

Restaurants

  • Trunk Bay Beach Bar
    20 min drive
  • Maho Crossroads
    28 min drive
  • Cruz Bay Landing
    8 min drive
  • Shambles
    10 min drive
  • The Longboard
    8 min drive

Frequently asked questions

Does Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views have a pool?

Yes, this property has a pool.

Is Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views pet-friendly?

No, pets are not allowed at this property.

How much is parking at Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views?

On-site parking is available at the property.

What time is check-in at Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views?

Check-in begins at 4:00 PM.

What time is check-out at Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views?

Checkout is at 10:00 AM.

Where is Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views located?

Situated in the mountains, this villa is steps from Sunset Beach and 2.1 mi (3.4 km) from Virgin Islands National Park. Devers Bay and Hart Bay are also within 5 minutes.

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Reviews

Tradewinds of Hart Bay - Beautiful Home, Pool, A/C, Stunning Views Reviews

10

Exceptional

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 8 out of 8 reviews
Rating 8 - Good. 0 out of 8 reviews
Rating 6 - Okay. 0 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 6 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Better than the Pictures

Hosts were incredibly responsive and had great advice about more than just the property. They recommended a provisioning service that delivered so the house was totally set up the minute we walked in the door. The rooms were bigger and better than they appear in the photos. The kitchen was significantly better and well equipped with tupperware. A perfect St. John rental.
Stayed 7 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome get away

Property was fantastic and St. John’s was/is beautiful!
Stayed 3 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Everything you need for an island vacation!

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!
Stayed 6 nights in Jul 2025