Luxury Villas in Chocolate Hole, St. John with Private Pools & Beachfront Access

Why Rent a Private Villa in Chocolate Hole, St. John?

With over half of the island protected as national parkland, St. John offers a rare balance of untouched natural beauty and refined comfort. Our villas in St. John range from beachfront homes near Cruz Bay to serene retreats in Coral Bay, all surrounded by the island’s lush landscapes and crystal-clear waters. Each St. John villa is thoughtfully designed with expansive open-air living spaces, private pools, and generous layouts that cater to families, couples, or groups of friends seeking privacy and relaxation. Many of our luxury villas in St. John are pet-friendly, so your dogs can join the adventure too. For those seeking comfort and convenience, these private villa rentals in St. John offer everything you need for an unforgettable stay, from personalised concierge services to close access to pristine beaches and local restaurants.

These are the 5 most popular villa rentals in Chocolate Hole, St. John. Narrow your search above.

  • From $714 to $1,071 per night
  • Pool
  • AC

Kismet

6 Bedrooms
6+ Bathrooms
  • From $3,286 to $4,286 per night
  • Pool
  • AC
  • From $710 to $1,643 per night
  • Pool
  • AC
  • From $620 to $1,320 per night
  • Near Beach
  • Pool
  • AC
  • From $1,000 to $2,143 per night
  • Near Beach
  • Pool
  • AC

About Chocolate Hole, St. John

Chocolate Hole is a beautiful area in St. John, US Virgin Islands, known for its stunning views of the Caribbean Sea and the lush vegetation of the surrounding hills. It’s a great spot for swimming, sunbathing and snorkeling. The beach is lined with swaying palm trees and white sand, and the sparkling waters are perfect for taking a dip.

The main attraction of Chocolate Hole is the crystal clear waters that provide plenty of opportunities for exploring the vibrant marine life of the area. From colorful coral to a wide variety of fish, there’s something to see below the surface. You can also spot sea turtles, sea urchins and even dolphins.

On the beach, there are plenty of activities to enjoy. There are areas for both sunbathing and picnicking, and the shallow water makes it a great spot for children. There are also plenty of vendors selling food, drinks, and souvenirs.

Chocolate Hole is a great place to relax and take in the beauty of the Caribbean. From the pristine beaches to the crystal clear waters, it’s a great spot to enjoy a day in the sun. If you’re looking for a peaceful escape, Chocolate Hole is the perfect spot to visit.

What's Special About a Villa Holiday in Chocolate Hole, St. John?

On St. John, natural beauty and understated luxury blend into a relaxed way of life, where national parks, white-sand beaches, and calm turquoise waters shape the island’s character. Choosing a St. John vacation rental allows guests to experience this serene environment in a truly personal way. Unlike hotels, a private holiday home offers spacious layouts, the flexibility to create your own rhythm, and greater value for families and groups. A luxury villa in St. John places you close to adventures like snorkelling at Trunk Bay or hiking through tropical trails, while also offering the quiet luxury of private terraces, full kitchens, and ocean-facing living spaces to unwind in style.

In our handpicked collection of St. John holiday villas, you’ll find everything from contemporary estates to classic beachfront retreats. Many of our villas with private pools are designed for seamless indoor-outdoor living, complete with wraparound terraces, shaded dining areas, and open-air showers. For those travelling together, family-friendly villas in St. John provide thoughtful spaces that encourage connection without sacrificing privacy. From tranquil hideaways close to Coral Bay to stylish bases near Cruz Bay, our selection of exclusive villas and vacation rentals ensures your time here feels effortlessly grounded and genuinely special.

Chocolate Hole, St. John Villa Rental FAQ

Q: What makes Chocolate Hole in St. John such a unique holiday destination?
A: Chocolate Hole is a hidden gem on the island of St. John, offering a unique blend of untouched beauty and luxury amenities. From its stunning beaches and turquoise waters to the surrounding lush green hills, it's a paradise for nature lovers. The area is also known for its vibrant culture, local cuisine, and friendly community. Renting a villa here ensures you can enjoy all these unique features in style, privacy, and comfort.
Q: How does renting a villa in Chocolate Hole enhance the holiday experience?
A: Renting a villa in Chocolate Hole offers an unmatched level of exclusivity and privacy. It allows you to create a personalised holiday experience, whether it's enjoying a sunrise breakfast on your private terrace, hosting a BBQ for friends, or indulging in a nighttime dip in your private pool. It's like having your own luxury home, but set in the stunning landscape of Chocolate Hole.
Q: What local attractions can we visit while staying in Chocolate Hole?
A: Chocolate Hole is conveniently located near many of St. John's best attractions. You can explore the Virgin Islands National Park, famous for its hiking trails and snorkelling spots, or visit the Annaberg Sugar Plantation to learn about the island's history. For a unique dining experience, the nearby Mongoose Junction offers a variety of local and international cuisines.
Q: What water activities are available in Chocolate Hole?
A: Chocolate Hole is a haven for water sports enthusiasts. The calm and clear waters make it a perfect spot for snorkelling, kayaking and sailing. A variety of sea life including colourful fish, sea turtles, and vibrant coral reefs can be spotted here. Fishing charters and boat tours are also available for a memorable day on the water.
Q: Are there any local festivals or events in Chocolate Hole?
A: St. John is famous for its lively festivals and events. The most renowned is the St. John Carnival, a month-long celebration in June and July featuring parades, music, food, and cultural performances. While staying in Chocolate Hole, you can easily join the festivities and experience the vibrant local culture firsthand.
Q: What dining experiences can we look forward to in Chocolate Hole?
A: The area offers a diverse range of dining options, from casual beachfront cafes to upscale restaurants serving gourmet cuisine. Seafood is a local specialty, and many establishments offer fresh catches of the day. Dining in Chocolate Hole offers not only delicious food but also stunning views of the Caribbean Sea, making every meal a memorable experience.
Q: How can we experience the local culture while staying in a villa in Chocolate Hole?
A: Staying in a villa in Chocolate Hole gives you the opportunity to live like a local. You can shop at nearby markets for fresh produce, join community events, or even hire a local chef to prepare a traditional Caribbean meal in your villa. It's not just about luxury and privacy, but also about immersing yourself in its unique culture.