Photo by Vada Stevens

Estate Chocolate Hole and Great Cruz Bay vacation rentals

We found 3,321 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 44 houses, 83 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

Showing deals for:Dec 19 - Dec 26

Image gallery for Private cliffside retreat full of magic. 9 bedrooms, 21 beds - infinity pool.

Come Spoil Yourself at Spirit on the Water!
9.8 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)

Private cliffside retreat full of magic. 9 bedrooms, 21 beds - infinity pool.

St. Thomas, Virgin Island

9% off
Price is $5,763
$40,341 for 7 nights
All fees included
Private cliffside retreat full of magic. 9 bedrooms, 21 beds - infinity pool.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Estate Chocolate Hole and Great Cruz Bay

Find out more about Estate Chocolate Hole and Great Cruz Bay

Why visit Estate Chocolate Hole and Great Cruz Bay

  • Stunning Beaches: Experience the beautiful Chocolate Hole Beach and other picturesque spots along the south coast.
  • Outdoor Activities: Engage in exciting water sports and outdoor adventures that showcase the area's natural beauty.
  • National Park Access: Explore the nearby national park, offering hiking trails and breathtaking scenery.
  • Charming Accommodations: Choose from a range of beachfront rentals, luxurious villas, and cozy condos for your stay.
  • Vibrant Atmosphere: Immerse yourself in the lively ambiance that invites relaxation and adventure.

Popular types of accommodation in Estate Chocolate Hole and Great Cruz Bay

Planning a getaway to Estate Chocolate Hole and Great Cruz Bay? Your adventure begins with selecting the perfect accommodations. Explore a variety of options, including charming condos, luxurious villas, and houses. Whether you're seeking beachfront rentals or Caribbean villas, you'll find ideal options to suit your needs. Discover the best of St. John with our curated selection of villa rentals and nearby hotels, ensuring a memorable and relaxing stay.

  • Condos: A highly sought-after option among travelers, condos offer a blend of comfort and convenience, perfect for enjoying the stunning views of Estate Chocolate Hole and Great Cruz Bay.
  • Villas: These luxurious accommodations provide spacious living and private amenities, ideal for those seeking a lavish getaway in paradise.
  • Houses: Perfect for families or groups, these homes offer a home-like atmosphere and ample space to relax during your stay.
  • Apartments: A practical choice for budget-conscious visitors, apartments provide essential amenities and are often located close to local attractions.
  • Cottages: Quaint and charming, cottages offer a cozy retreat, perfect for couples looking for a romantic escape.**

Top attractions near Estate Chocolate Hole and Great Cruz Bay

Estate Chocolate Hole and Great Cruz Bay is perfect for beach and outdoor enthusiasts seeking stunning scenery. Popular attractions include Chocolate Hole Beach, Coral Bay, and the nearby national park. Visitors can enjoy a variety of activities that highlight the area's natural beauty, making it an ideal destination for relaxation and adventure in the U.S. Virgin Islands.

  • Trunk Bay: Known for its stunning beach vibes, Trunk Bay features crystal-clear waters and soft white sand. It's perfect for swimming, snorkeling, and soaking up the sun, making it a must-visit for beach lovers.
  • Virgin Islands National Park: This national park offers a unique blend of adventure and breathtaking scenery. Explore hiking trails, discover rich wildlife, and enjoy outdoor activities amidst lush landscapes and coastal views.
  • Cinnamon Bay Beach: With its beautiful bay setting, Cinnamon Bay Beach invites you to enjoy beach activities and outdoor adventures. Experience serene scenery while relaxing or exploring the vibrant marine life.

Things to do recommended for couples

For a romantic getaway in Estate Chocolate Hole and Great Cruz Bay, indulge in a rejuvenating body treatment at The Self Centre, just 2 miles away, or enjoy breathtaking views on the Skyride to Paradise Point, located 9 miles away. Perfect experiences for couples.

Things to do recommended for families

Families visiting Estate Chocolate Hole and Great Cruz Bay can enjoy a fun day at Lionel Roberts Stadium, located 10 miles away, where they can soak up the sports atmosphere and engage in various activities suitable for all ages.

Things to do recommended for groups

Experience the vibrant local culture with a visit to St. John Spice, a unique store, and Mongoose Junction, a lively shopping center, both just 1 mile from your base. For adventure seekers, the St. John Eco Hike & Snorkel Adventure offers breathtaking outdoor scenery, also located 1 mile away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Estate Chocolate Hole and Great Cruz Bay

When planning your trip, whether you're traveling with a group, with family, bringing along pets, or looking for extended stays, be sure to adjust your filters according to your top priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Estate Chocolate Hole and Great Cruz Bay with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Estate Chocolate Hole and Great Cruz Bay with young kids: Traveling with little ones can be a bit daunting. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, considering how close you are to family-friendly attractions can make a significant difference in your trip.
  • Taking your pets with you to Estate Chocolate Hole and Great Cruz Bay: For many families, a getaway isn't truly special unless their furry companion is along for the ride. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Estate Chocolate Hole and Great Cruz Bay: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria, as well.

Where to stay in Estate Chocolate Hole and Great Cruz Bay

Estate Chocolate Hole and Great Cruz Bay offers a delightful blend of tropical charm and stunning seaside experiences. Explore the picturesque beaches along the south coast, where you can soak up the sun or partake in exciting water activities. The area's vibrant atmosphere invites you to embark on excursions that showcase the natural beauty of St. John. Whether you're seeking relaxation or adventure, this destination promises unforgettable memories amid breathtaking scenery.

  • St. John: St. John, a picturesque district in the U.S. Virgin Islands, is renowned for its stunning natural beauty and outdoor adventures. Nestled among lush landscapes, Estate Chocolate Hole and Great Cruz Bay are located here, providing easy access to breathtaking beaches and the Virgin Islands National Park. Visitors can enjoy snorkeling, hiking, and exploring vibrant coral reefs. The island's charming resorts and local eateries enhance the experience, making St. John a perfect blend of relaxation and adventure.
  • Monte: Monte is a quaint village located just half a mile from Estate Chocolate Hole and Great Cruz Bay, making it an ideal spot for travelers looking to delve deeper into St. John’s charm. Known for its serene beaches and scenic views, Monte offers opportunities for outdoor activities such as snorkeling and kayaking. The local resorts provide comfort and hospitality, while nearby stores allow visitors to shop for unique souvenirs. Monte’s close proximity to the natural beauty of the national park makes it a must-visit destination.
  • Estate Enighed: Located 0.9 miles from Estate Chocolate Hole and Great Cruz Bay, Estate Enighed is a vibrant village that attracts tourists seeking sun-soaked beaches and outdoor exploration. The area boasts a variety of resorts and hiking trails that cater to both relaxation and adventure enthusiasts. Visitors can partake in thrilling water sports or simply unwind on the sandy shores. With its stunning bay views and access to the national park, Estate Enighed offers an unforgettable experience for those looking to enjoy the pristine landscapes of St. John.

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can really help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your needs.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn valuable OneKeyCash with your booking. Being the planner has its perks. When you join our travel rewards program, One Key, you'll gain immediate access to exclusive member savings and can earn and redeem OneKeyCash on eligible reservations. Sign up today and start enjoying the benefits.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for planning your next adventure, managing your travel arrangements, and reviewing your existing bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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 best area to stay in Estate Chocolate Hole And Great Cruz Bay when booking a vacation rental?
When considering a vacation rental in Estate Chocolate Hole and Great Cruz Bay, U.S. Virgin Islands, the neighborhoods of Great Cruz Bay and Chocolate Hole stand out as excellent options. Great Cruz Bay is particularly appealing for its proximity to the beach and vibrant dining scene, making it a great spot for those looking to enjoy both relaxation and local cuisine. The nearby Honeymoon Beach is a top attraction, renowned for its crystal-clear waters, ideal for swimming and snorkeling.

Chocolate Hole, on the other hand, offers a more tranquil setting with stunning waterfront views. This area is great for vacationers who desire a peaceful escape while still being close to the lively activities in Great Cruz Bay. The Virgin Islands National Park is easily accessible from here, providing opportunities for hiking, exploring nature, and appreciating the breathtaking landscapes of the islands.

Both neighborhoods typically feature a variety of vacation rental properties, suiting different preferences and budgets. With around a hundred options available, visitors can find accommodations ranging from cozy villas to luxurious beachfront homes, ensuring a memorable stay in this idyllic destination.
How much does it cost to rent a vacation home in Estate Chocolate Hole And Great Cruz Bay?
Prices for vacation rentals in Estate Chocolate Hole And Great Cruz Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Estate Chocolate Hole And Great Cruz Bay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Estate Chocolate Hole And Great Cruz Bay vacation house rentals?
You can find great discounts on house rentals in Estate Chocolate Hole And Great Cruz Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Estate Chocolate Hole And Great Cruz Bay?
A long-stay vacation rental in Estate Chocolate Hole And Great Cruz Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Estate Chocolate Hole And Great Cruz Bay vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Estate Chocolate Hole And Great Cruz Bay with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
How early should I book a Estate Chocolate Hole And Great Cruz Bay vacation rental?
Book your Estate Chocolate Hole And Great Cruz Bay vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Estate Chocolate Hole And Great Cruz Bay?
In Estate Chocolate Hole and Great Cruz Bay, visitors can enjoy a range of attractions that showcase the natural beauty and cultural heritage of the U.S. Virgin Islands. The area is known for its stunning beaches, with Great Cruz Bay Beach offering calm waters ideal for swimming and kayaking. Nearby, the Virgin Islands National Park provides opportunities for hiking and exploration, featuring trails that lead to breathtaking views and historic ruins.

Additionally, the charming town of Cruz Bay is just a short distance away, where travelers can find shops, restaurants, and art galleries that reflect the local culture. The vibrant atmosphere in Cruz Bay is superb for enjoying the local cuisine and nightlife. For those interested in water activities, nearby snorkeling spots such as Trunk Bay offer incredible underwater experiences with diverse marine life.
Can I change or cancel my Estate Chocolate Hole And Great Cruz Bay home rental booking on Vrbo?
To find Estate Chocolate Hole And Great Cruz Bay vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Estate Chocolate Hole And Great Cruz Bay vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Vacation Ideas

More Vacation Ideas