Estate Chocolate Hole and Great Cruz Bay vacation rentals

We found 3,530 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 54 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.

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

Showing deals for:Jan 15 - Jan 22

Image gallery for Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

Incredible view of Caribbean Sea.
10 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

8% off
Price is $132
$921 for 7 nights
All fees included
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

Find spaces that suit your style

Find the best place to stay - Estate Chocolate Hole and Great Cruz Bay

Image of Pet friendly. Kayak, paddle board, snorkel, or hike to the beach.
Premier Host

Pet friendly. Kayak, paddle board, snorkel, or hike to the beach.

Sleeps 10 · 5 bedrooms · 5+ bathrooms
9.4 out of 10
exceptional
(70 reviews)
More information about Pet friendly. Kayak, paddle board, snorkel, or hike to the beach., opens in a new tab

Top rated rentals - Estate Chocolate Hole and Great Cruz Bay

Outdoor dining
Premier Host
Adequate Accommodations
10.0 out of 10, Exceptional, 115 reviews
"This small cottage is in a convenient and quiet location. We had easy access to Cruz Bay and everything we needed. The accommodations are adequate, generally speaking. The bed was comfortable, and the kitchen and bathroom had everything we needed. Not everyone likes or needs air conditioning, but we like it when we sleep and we found the unit to be louder than ideal, but we managed. The hosts were communicative and quick to respond when we needed the propane tank for the house’s oven/range...
T B.
T B.
Stayed Jun 2025
Cute Cozy Cottage with private entrance and ocean views in prime neighborhood

  • 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

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.

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.

Frequently Asked Questions

What is the best area to stay in Estate Chocolate Hole And Great Cruz Bay, U.S. Virgin Islands when booking a vacation rental?

When considering a vacation rental in Estate Chocolate Hole and Great Cruz Bay, you'll find a range of appealing neighborhoods to choose from. One of the standout areas is Great Cruz Bay itself, which is known for its beautiful beachfront and proximity to local attractions. Here, you can enjoy easy access to the tranquil waters great for swimming and snorkeling, as well as the scenic views that define the U.S. Virgin Islands.

In addition to its stunning beaches, Great Cruz Bay is close to several delightful dining options and shops that provide a taste of local culture. For those who enjoy outdoor activities, the nearby Virgin Islands National Park offers hiking trails with breathtaking vistas and opportunities to explore the rich biodiversity of the region.

On the other hand, Estate Chocolate Hole is another charming neighborhood that offers a more serene and private atmosphere. This area is known for its luxurious villas and beautiful landscapes, providing a great backdrop for relaxation. Visitors can easily access nearby attractions such as the pristine beaches and vibrant marine life that make the islands so special.

Overall, both neighborhoods offer a variety of properties, from cozy rentals to upscale villas, suiting different preferences and budgets.

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, U.S. Virgin Islands?

In Estate Chocolate Hole and Great Cruz Bay, visitors can enjoy a blend of natural beauty and local charm. The beaches in this area, such as Chocolate Hole Beach, offer stunning views and opportunities for snorkeling and swimming in crystal-clear waters. Great Cruz Bay is known for its picturesque marina, where travelers can find various boat tours and water activities, making it a great spot for those looking to explore the surrounding islands.

Nearby, the Virgin Islands National Park provides hiking trails and access to unspoiled beaches, showcasing the lush vegetation and diverse wildlife of the region. This area is also close to local dining options and shops, allowing visitors to indulge in the local cuisine and culture.

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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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.

What is VrboCare™ and how does it work?

Vrbo’s mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you’re protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can’t resolve, we’ll help you address it, find a similar property, or get your reservation refunded if applicable. That’s our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.

What can I expect from Vrbo customer service and VrboCare™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.

Can I plan a group trip on Vrbo?

Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More vacation ideas