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Chocolate Hole Villas & Vacation Rentals

These are the 7 most popular villa rentals in St. John. Narrow your search above.

Artfully designed, Sea Stone provides the perfect Caribbean getaway for one or two couples looking for rest and relaxation. The villa was created to allow easy access in and out ...
Sea Stone Villa sits near Maria Bluff and has amazing Caribbean Views

Chocolate Hole, St. John

Pool | AC

Details
Guests of Kismet can enjoy both sunrise and sunset views, is surrounded by gorgeous tropical gardens. Its perfect for special events like weddings and receptions. There's three separate bedroom pavilions, ...
Kismet Villa Estate is located on a hilltop over Maria Bluff

Kismet

6 6+

Chocolate Hole, St. John

Pool | AC

Details
The Last Resort stands true to its name…it’s certainly a paradise and feels like a mini-resort. This beautiful estate sits elevated between Chocolate Hold and Hart Bay with ...
The Last Resort Villa located in Chocolate Hole

Chocolate Hole, St. John

Pool | AC

Details
Coyaba has a great pool area and views. It's pretty private but is still only a short drive from the North Shore and even closer to restaurants and the grocery ...
Coyaba Villa is located on the hillside overlooking Devers Bay

Chocolate Hole, St. John

Pool | AC

Details
Tre Vista is a super tranquil, comfortable villa perfect for you and your closest friends. There's a separate suite for kids or teenagers, a guest cottage, and a big pool ...
Tre Vista Estate sits on a hillside overlooking Great Cruz Bay

Chocolate Hole, St. John

Pool | AC

Details
The layout of Reefside ensures that everyone in your party has beautiful rooms, private bathrooms, and complete privacy. The common areas are comfortable and spacious, and the pool deck is ...
Views into Chocolate Hole Bay from Reefside Villa
Specials.

Chocolate Hole, St. John

Near Beach | Pool | AC

Details
Ciellodonna’s best feature is easy to name: location, location, location. The villa is less than 10 minutes from Cruz Bay’s restaurants and boutiques, and its waterfront location provides easy ...
Ciellodonna has a great deck to enjoys beautiful bay vies

Chocolate Hole, St. John

Near Beach | Pool | AC

Details
Sunrise
Sunset
Sunrise and sunset vary based on time of year. You can change the date to see the how the sunrise and sunset are affected.
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Looking to rent a villa in St. John?

  1. Over half of St. John makes up a lush national park, and ecotourism dominates
  2. Villa guests on St. John can expect miles of scenic hiking trails, natural beauty, and peaceful nature views
  3. Contact our St. John villa experts and find the perfect villa for your island getaway

Planning a trip to St. John, US Virgin Islands? We have collected an extensive listing of villas for rent, most personally verified by our villa experts. If you want to enjoy your vacation in a relaxing environment with all the comforts of home, then a St. John villa is exactly what you need. With so my of the island protected by National Park, the private villas are often secluded and spectacular. Ideal for couples, families, and friends traveling together, these private villas offer space, seclusion, and easy access to the attractions on St. John.

What's special about St. John?

As part of the U.S. Virgin Islands, St. John is unique in its “American” style, ecologically friendly attitude, and its miles of scenic national park land. This is the smallest of the three main islands that comprise the USVI, and about 2/3 of it is protected park land, with miles of hiking trails among the trees, cacti, and other tropical plants. St. John is definitely less developed than the other islands, so if what you want is peace, quiet, and tons of natural beauty, then this is the place to be.

As mentioned, hiking is a favorite activity on the island, and there are lots of paths and trails to enjoy, or you can just take a stroll along the beach and enjoy the view. St. John also has something that the other Caribbean islands don’t - snuba. A combination of snorkeling and scuba diving, snuba is a fun way to check out the underwater sights the island has to offer.

St. John is definitely all about enjoying the outdoors, but that is not to say that visitors won’t be able to partake in some excellent shopping, dining, and nightlife while on the island. Cruz Bay is a fun place to be day or night, and there are numerous shops on the island featuring jewelry, clothes, and other souvenirs to help you remember your tropical beach vacation. Restaurants serving up delicious Caribbean fare are plentiful, and the bars are open late to keep your party lasting well into the night.

While St. John does offer up villas or resort hotels for travelers to stay in, the island also features unique Caribbean campgrounds, or tent resorts. These beachfront areas have permanent canvas structures, food, supplies, and water sports on-site. While it’s a different take on the traditional hotel or resort, these campgrounds are environmentally-friendly, affordable, and give guests a closer connection to the island itself. Don’t worry if you’re not a camper; there are plenty of villas for rent as well, where you’ll get the comforts of home along with amazing views and island breezes. The hotels on the island, although fewer in number, offer a variety of accommodations and amenities to suit those travelers looking for room service and restaurants on-site.

Perfect for outdoor enthusiasts, beach lovers, or for those who just want to lounge around on a cool, laid back island, St. John is a Caribbean gem that will meet all your vacation requirements.

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