Four Winds

Four Winds Villa — Historic Caribbean Charm with Modern Comforts

Perched high on the ridge between Cane Garden Bay and Brewers Bay, Four Winds Villa is one of Tortola’s oldest and most character-rich homes, offering a rare blend of historic Caribbean charm and thoughtful modern upgrades. Set within a peaceful residential area, the villa enjoys cooling trade winds, sweeping views, and convenient access to Road Town, two of the island’s most beloved beaches, and nearby National Parks, an ideal base for swimming, hiking, and island exploration.

Originally built in the late 1800s, Four Winds has been lovingly refreshed by its current owners, preserving the soul of traditional West Indian architecture while introducing modern comforts for today’s traveler. The property is made up of multiple charming structures connected by stone pathways, wooden decks, and lush tropical gardens, creating a sense of stepping back in time while still enjoying relaxed island living.

Upon arrival, guests are welcomed into a sunken, garden-wrapped courtyard, a private, open-air living space shaded by mature trees. This tranquil spot is perfect for morning yoga, afternoon tea, or a West Indian–style BBQ prepared by your pre-arranged local chef, and serves as the heart of the villa.

The main house is anchored by an expansive shaded wooden deck overlooking Cane Garden Bay, perfectly positioned for golden sunsets and evening breezes. This deck flows seamlessly into both the living room and the master suite, allowing for effortless indoor-outdoor living. Inside, warm wooden floors, exposed white ceilings, curated local artwork, and traditional furnishings reflect the villa’s rustic Caribbean heritage.

The fully air-conditioned master bedroom features a king-size sleigh bed, romantic mosquito-net canopy, and timeless island character. The newly upgraded bathroom, with a spacious walk-in shower, is conveniently located just off the main living area.

With wide wooden doors thrown open to capture the trade winds, the living room offers a cool retreat from the midday sun or a cozy hideaway on rainy afternoons. High-speed internet, a large smart TV, and a curated selection of books and games ensure comfort and entertainment, while the light-filled, fully equipped kitchen has everything needed for home cooking.

Up stone steps and separate from the main house, the Lime House is one of the oldest surviving structures on Tortola. This fully air-conditioned cottage features a queen-size bed, a newly renovated ensuite bathroom, and a hidden private courtyard – a peaceful nook for morning coffee. A beautiful Joseph Hodge painting above the bed whimsically depicts the Lime House’s historic past, offering a rare and authentic connection to the island’s heritage.

After a day exploring the BVI, wander through vibrant gardens, past the villa’s original brick oven, and slip into your private pool surrounded by swaying palms. As the sun sets behind the USVI and the coqui frogs begin their nightly chorus, enjoy a homemade rum punch and embrace the timeless rhythm of Caribbean life.

Four Winds Villa offers an intimate blend of BVI history, rustic elegance, serene privacy, and modern comfort, ideal for honeymooners, pre- or post-yacht charter stays, and travelers seeking a truly unique island escape filled with character and soul.

Optional Accommodation – Stone House
An additional fully air conditioned separate unit is available on the property. The Stone House features a queen-size four-poster bed and a large deck surrounded by greenery, ideal for reading, meditation, or yoga. This unit shares bathroom facilities with the main house. Please refer to our 3D tour and inquire for further details regarding availability.

1 King Master & 2 Queens

Doors and windows are screened

Ceiling fans in each room

AC – Bedrooms Only

Reliable WiFi

SmartTV with Netflix

Maid service – Once Weekly

Propane BBQ

Washer and Dryer