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Estate Chocolate Hole and Great Cruz Bay vacation rentals

We found 3,303 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Estate Chocolate Hole and Great Cruz Bay by choosing from 45 houses, 82 condos, and other vacation rentals. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, such as air conditioning and a TV. Whatever you're looking for, you're sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Estate Chocolate Hole and Great Cruz Bay

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Choose a vacation rental for your Estate Chocolate Hole and Great Cruz Bay getaway

Learn about the unique charm of Estate Chocolate Hole and Great Cruz Bay with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

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.

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.

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 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.

Transportation to and around Estate Chocolate Hole and Great Cruz Bay

The nearest airport is in Cyril E. King Airport (STT), located 12.4 mi (19.9 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to St. Thomas (SPB-St. Thomas Seaplane Base), which is 10.4 mi (16.7 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Estate Chocolate Hole and Great Cruz Bay?
The most desirable types of vacation rentals in Estate Chocolate Hole and Great Cruz Bay are villas. Ready for more choices? Vrbo offers a variety of options to match our guests’ diverse needs, so you’ll see vacation properties in all shapes and sizes. The ideal fit is ready and waiting for you — snap up yours today.
How much does it cost to rent a vacation rental in Estate Chocolate Hole and Great Cruz Bay?
The average price for a vacation home in Estate Chocolate Hole and Great Cruz Bay is determined by a number of factors, including length of stay, property type and season. Whether you’re searching for a sprawling villa with space for the whole family or a quaint cottage just enough for two, just enter your dates of travel to find stays with amazing value.
How much does it cost to rent a beach house in Estate Chocolate Hole and Great Cruz Bay?
When you travel and the size and style of the property will influence the cost of your beachside escape. Put in your Estate Chocolate Hole and Great Cruz Bay travel dates to view your options on Vrbo. Can’t live without a hot tub? Use our filters to pick the features and amenities you want in your vacation home.
Are there pet-friendly vacation rentals in Estate Chocolate Hole and Great Cruz Bay?
Yes. There are. You can choose from 661 vacation rentals that cater to pets in Estate Chocolate Hole and Great Cruz Bay. Lots of our pet-friendly vacation rentals even come with a backyard for your fur baby to play in, doggie beds, complimentary treats and proximity to parks. Apply the “Pets allowed” filter to find your place on Vrbo.
Can I rent a house with a pool in Estate Chocolate Hole and Great Cruz Bay?
Add an extra layer of fun to your adventure by booking your crew into one of the 609 houses with a private pool in Estate Chocolate Hole and Great Cruz Bay. Use our search filter to find properties with pools on Vrbo, then spend carefree days splashing and playing in a swimming pool that’s all yours.
What are popular rental amenities in Estate Chocolate Hole and Great Cruz Bay?
Some of the most popular rental amenities people look for in Estate Chocolate Hole and Great Cruz Bay include a nearby river, a sauna and tennis. Whether you’re going on vacation with family, friends or even pets, Vrbo vacation homes feature the best amenities for starting a new adventure with the people who matter most.
Are there large group vacation rentals in Estate Chocolate Hole and Great Cruz Bay?
With 228 properties that can host 10 people or more in Estate Chocolate Hole and Great Cruz Bay, there’s no need to limit the invite list. From family get-togethers to events like Christmas or New Year’s Eve parties, Vrbo can help you find a large group rental to match the occasion.
Are there vacation rentals in Estate Chocolate Hole and Great Cruz Bay that welcome kids?
With 653 family-friendly vacation homes available in Estate Chocolate Hole and Great Cruz Bay, now is the perfect time to introduce your children to the thrills of travel. Simply click on our “Properties good for families” filter to view stays that come with amenities perfect for families on the move, such as dining rooms, outdoor spaces, hot tubs and entertainment areas.
What are the top attractions for families in Estate Chocolate Hole and Great Cruz Bay?
Have a fun day out with the whole family at Chocolate Hole Beach. This major attraction is close to the center of Estate Chocolate Hole and Great Cruz Bay.
Are there one-bedroom vacation rentals in Estate Chocolate Hole and Great Cruz Bay?
Yes, you can choose from 72 one-bedroom rentals in Estate Chocolate Hole and Great Cruz Bay. Whether you’d prefer a townhouse or a cabin, Vrbo’s one-bedroom rentals are ideal if you don’t require tons of space. One of the main perks of having your own pad? You’ll never need to share your vacation with strangers.
Can I find two-bedroom vacation rentals in Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay has 295 two-bedroom vacation properties to choose from. Enjoy a vacation home with all the comfort and privacy you’re looking for at a price that won’t break the bank on Vrbo.
Are there vacation rentals with WiFi in Estate Chocolate Hole and Great Cruz Bay?
You can pick from 72 vacation rentals with WiFi in Estate Chocolate Hole and Great Cruz Bay. If you want to disconnect from the world during your trip, but still need to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay has 638 vacation rentals where you can relax and recharge in air-conditioned comfort. To locate a stay on Vrbo that offers this perk, enter your desired travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Estate Chocolate Hole and Great Cruz Bay?
The minimum age is normally 16, 18 or 21. It can vary across properties on Vrbo, so check the rules of your chosen Estate Chocolate Hole and Great Cruz Bay stay before making a booking.
How long can I rent a vacation rental in Estate Chocolate Hole and Great Cruz Bay for?
How long you can book a vacation rental in Estate Chocolate Hole and Great Cruz Bay depends on the property. Simply enter your chosen travel dates to see a list of options offering extended stays. With loads of features such as air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you’re sure to get the perfect place to call your home away from home in Estate Chocolate Hole and Great Cruz Bay.
Does Vrbo offer discounts for vacation homes in Estate Chocolate Hole and Great Cruz Bay?
In Estate Chocolate Hole and Great Cruz Bay, you’ll find some incredible bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re planning a weekend getaway or a couple of weeks away, we’ve got a variety of options to suit your style.

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