Discover a selection of 2,000 vacation rentals in Estate Chocolate Hole and Great Cruz Bay that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $225 per night, and villas and houses are popular options for a stay in Estate Chocolate Hole and Great Cruz Bay. Either way, you'll find a rental for everyone's needs.
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Destination guide

Explore Estate Chocolate Hole and Great Cruz Bay

The beautifully-manicured beach, turquoise waters and kid-friendly activities at Saint John's Great Cruz Bay are the perfect bedfellows for the neighboring harbor of Chocolate Hole, a quiet spot popular with fishermen and locals alike. Dotted between the 2 areas, Estate Chocolate Hole and Great Cruz Bay vacation rentals offer the ideal base for getaways with families, friends or both. You'll find these rentals within easy reach of shopping and dining at Cruz Bay and the postcard-worthy scene at Trunk Bay Beach, not to mention the many natural delights within the Virgin Islands National Park.

Things to do

Inland attractions in Estate Chocolate Hole and Great Cruz Bay

While offshore pastimes frequently lead the way, inland Saint John also has plenty to offer. The bustling town of Cruz Bay serves up a tempting selection of waterfront dining spots and boutique shopping at the popular Mongoose Junction, though it's often the Virgin Islands National Park that turns out to be the star turn. Covering well over half the island, this vast expanse of tropical landscape hosts popular attractions such as the landmark Annaberg Plantation ruins and the Cinnamon Bay Archeology Museum, not to mention a meandering network of scenic hiking trails that offer the perfect setting for a little downtime.

Activities

Estate Chocolate Hole and Great Cruz Bay adventures

Basking in the warm, shallow waters that surround Saint John is a must-do for visitors. Teeming with colorful marine fish, as well as turtles and seahorses, these waters are best explored with the help of a kayak, paddleboard or snorkel gear, all of which will be available to hire from various points close to your Estate Chocolate Hole and Great Cruz Bay vacation rental. You might choose to explore under your own steam or prefer a local to guide the way, but whether it's hiking along Turtle Point Trail beside Caneel Bay or kayaking through Hurricane Hole's mangrove forest, outdoor adventure is never far away.

Weather

Winter sun in Estate Chocolate Hole and Great Cruz Bay

Demand for Estate Chocolate Hole and Great Cruz Bay vacation rentals is at its highest during the winter months of December through March. Travelers flock to the island to enjoy perpetual sunny days and refreshingly-breezy nights, so it's wise to book your preferred rental early. Temperatures are glorious between July and October, though rain is typical during a season that is renowned for hurricanes. Compromise can often be found in April and May. There's less going on, but blissful days are all but guaranteed.

Natural features

Natural wonders in Estate Chocolate Hole and Great Cruz Bay

Natural wonders can be found around every corner on Saint John, the smallest of the U.S. Virgin Islands, and there are many must-see attractions to tell your friends about. In nearby Fish Bay, it's possible to share the clear, shallow waters with juvenile nurse sharks, while to the north, the summit of Peace Hill offers enchanting views of Saint Thomas and the British Virgin Islands. An outing to the eastern coast provides a different flavor of Caribbean life, one that's a great deal quieter than that found in lively Cruz Bay.

How many vacation rentals are available around Estate Chocolate Hole and Great Cruz Bay?

Our 2021 property listings offer a large selection of 1,971 vacation rentals around Estate Chocolate Hole and Great Cruz Bay. From 637 villa rentals to 897 house rentals, find the best place to stay with your family and friends to discover the Estate Chocolate Hole and Great Cruz Bay area.

Can I rent Villas in Estate Chocolate Hole and Great Cruz Bay?

Yes, of course. Vrbo has 637 Villas in Estate Chocolate Hole and Great Cruz Bay. Our other popular types of vacation rentals in Estate Chocolate Hole and Great Cruz Bay include:

  • Houses: 897 rentals available
  • Condos/Apartments: 765 rentals available
  • Studios: 217 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Estate Chocolate Hole and Great Cruz Bay?

Yes, you can select your preferred vacation rental with pool among our 1,556 vacation rentals with pool available in Estate Chocolate Hole and Great Cruz Bay. Please use our search bar to access the selection of vacation rentals available.