Estate Chocolate Hole and Great Cruz Bay vacation rentals

We found 3,494 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:Dec 11 - Dec 18

Spacious King Primary Suite ...
Down Island Atlantic Ocean Views of BVI and St John from the main floor deck
Watch the Sunset and star gaze...
Hans Lollick views from the Dining table.
Exceptional
(30 reviews)

Villa STARGATE welcomes you to an island escape where the sky meets the sea.

St. Thomas

5% off
CA $1,224
CA $10,990 total
Villa STARGATE welcomes you to an island escape where the sky meets the sea.
Patio off main level
Outdoor entertainment area
Property grounds
Main level living room
Exceptional
(44 reviews)

Minutes from Magens Bay, gated property, large pool & outdoor entertainment area

St. Thomas

10% off
CA $621
CA $5,923 total
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
Exterior
Property grounds
Interior
Room
Exceptional
(30 reviews)

Flamingo Grove Glamping Site with AC

St. John

5% off
CA $222
CA $1,983 total
Flamingo Grove Glamping Site with AC
Private kitchen
Interior
Aerial view
Interior
Wonderful
(21 reviews)

Cozy stay, next to lookout and 10 minutes for Magens Bay Beach

St. Thomas

6% off
CA $203
CA $1,849 total
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
Dining
Our coconut tree. We have seen giant barracuda, eagle rays, sting rays, turtles
Approach to the house - plenty of parking.
Interior
Exceptional
(36 reviews)

SPECIAL PRICING! !!

St. Thomas

10% off
CA $660
CA $6,172 total
SPECIAL PRICING! !!
Private kitchen
Outdoor dining
Property grounds
Private kitchen
Exceptional
(141 reviews)

Lameshur Cottage's Guest House

St. John

10% off
CA $355
CA $3,162 total
Lameshur Cottage's Guest House
Exterior
Terrace/patio
Interior
Property grounds
Exceptional
(27 reviews)

Authentic Island Stay, Budget-Friendly Cottage, Peaceful Setting, Stunning Views

St. John

10% off
CA $330
CA $3,176 total
Authentic Island Stay, Budget-Friendly Cottage, Peaceful Setting, Stunning Views
Outdoor dining
Pool
Property grounds
Private kitchen
Exceptional
(116 reviews)

AC & Trade winds, Huge VIEW, private, pool, gardens, perfect for couples or FAM.

St. John

5% off
CA $802
CA $7,355 total
AC & Trade winds, Huge VIEW, private, pool, gardens, perfect for couples or FAM.
Private kitchen
Property grounds
garden entrance
Pool
Exceptional
(113 reviews)

“Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”

St. John

10% off
CA $435
CA $3,546 total
“Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”
Dining table
Deck at night
Room
Pool at night (Old pool look)
Exceptional
(70 reviews)

3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor

St. Thomas

10% off
CA $872
CA $7,717 total
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
Entrance
Ahhh...
Kitchen
Pool side dining
Exceptional
(152 reviews)

Private Paradise! One level, panoramic views from every room!

St. Thomas

10% off
CA $995
CA $9,143 total
Private Paradise! One level, panoramic views from every room!
Exterior
Incredible view of Caribbean Sea.
Pathway to the airstream 😎
Dinette table east view to St. John.
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

10% off
CA $149
CA $1,225 total
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Room
Exterior
Interior
Property grounds
Exceptional
(8 reviews)

Octopus Den Glamping Site with AC

St. John

5% off
CA $222
CA $1,983 total
Octopus Den Glamping Site with AC
Room
Down Island View!
Bathroom
Kitchen/Dining
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

10% off
CA $560
CA $5,223 total
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Property grounds
Living area
Property grounds
Room
Exceptional
(69 reviews)

Affordable Solar powered 2-Bedroom Haven with Washer/Dryer, near Red Hook!

St. Thomas

5% off
CA $230
CA $2,243 total
Affordable Solar powered 2-Bedroom Haven with Washer/Dryer, near Red Hook!
Exterior
Property grounds
Private kitchen
Villa from the pond in kayak
Exceptional
(18 reviews)

"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.

St. John

10% off
CA $579
CA $4,456 total
"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.
Living room looking toward kitchen. 1st bedroom on the left, dining on the right
Ocean View from kitchen all the way to St. Croix
View from ocean view dining room towards kitchen and bedroom #1
Comfortable living room and open space kitchen
Exceptional
(18 reviews)

2-bedroom-ocean & St Croix views-5 minutes to Cruz Bay

St. John

5% off
CA $459
CA $3,732 total
2-bedroom-ocean & St Croix views-5 minutes to Cruz Bay
Private kitchen
Dining
Interior
Property grounds
Exceptional
(14 reviews)

Seaside Blue <br>Hosted by Shilpi Singh

St. Thomas

10% off
CA $218
CA $1,860 total
Seaside Blue <br>Hosted by Shilpi Singh
Property grounds
Pool
Private kitchen
Terrace/patio
Exceptional
(47 reviews)

Breathtaking Panoramic Views of the British Virgin Islands from hot tub & pool!

St. John

6% off
CA $438
CA $4,025 total
Breathtaking Panoramic Views of the British Virgin Islands from hot tub & pool!
Interior
Great Cruz Bay
Top pool with sunshade
walkway to the pools
Exceptional
(31 reviews)

Secluded Island Escape w/ King Bed, Lush Gardens & Shared Pool Access

St. John

5% off
CA $656
CA $5,855 total
Secluded Island Escape w/ King Bed, Lush Gardens & Shared Pool Access
Coffee maker, blender, toaster, kettle and air fryer all available for guest use
grab a frozen cocktail at Sapphire Beach Bar
Sapphire Bar & Grill offers American fare with a view
Beautiful landscaping around the property
Exceptional
(9 reviews)

Sapphire Beach Retreat - Luxury Oceanfront Gem!

St. Thomas

5% off
CA $556
CA $5,187 total
Sapphire Beach Retreat - Luxury Oceanfront Gem!
Another view from the kitchen window.
Sandy Spit - One of the many daytrip locations availble with a boat rental.
Master bedroom sliding door to patio and amazing view
Pool
Exceptional
(62 reviews)

READ MY REVIEWS! Vacation in style right on the ocean ABSOLUTELY THE BEST!

St. Thomas

10% off
CA $298
CA $2,820 total
READ MY REVIEWS! Vacation in style right on the ocean ABSOLUTELY THE BEST!
The Beach Bar with live music and grill on the property
Pool
The patio and beach right in front of you!
Socially distancing beach bar area for taking a drink or lunch to the beach
Exceptional
(65 reviews)

Beach, Bed and Beyond! WiFi included , New Tiled Shower!

St. Thomas

10% off
CA $498
CA $4,032 total
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
Beach
Our Actual Balcony and AMAZING OCEAN VIEW LOCATION!
Room
Living area
Exceptional
(157 reviews)

5★ SAPPHIRE SUNRISE-2 Story Direct Ocean Beachfront Villa- Luxe Reno!

St. Thomas

10% off
CA $621
CA $5,729 total
5★ SAPPHIRE SUNRISE-2 Story Direct Ocean Beachfront Villa- Luxe Reno!

Find out more about Estate Chocolate Hole and Great Cruz Bay

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.

Activities and attractions in and around Estate Chocolate Hole and Great Cruz Bay

Do you want to find things to do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Estate Chocolate Hole and Great Cruz Bay a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Mahogany Run Golf Course (8.4 mi / 13.5 km)
  • The Self Centre (2.1 mi / 3.4 km)

Exploring the natural features in Estate Chocolate Hole and Great Cruz Bay

Whether you're looking for fun outdoor activities or just want to take in the scenery, Estate Chocolate Hole and Great Cruz Bay is a great place to spend some time outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Sapphire Beach (4.4 mi / 7.1 km)
  • Chocolate Hole (0.3 mi / 0.5 km)
  • Great Cruz Bay (0.5 mi / 0.7 km)
  • Cruz Bay Beach (1.1 mi / 1.8 km)
  • Cruz Bay Visitor Center (1.2 mi / 1.9 km)
  • Honeymoon Beach (1.6 mi / 2.5 km)

Transportation to and around Estate Chocolate Hole and Great Cruz Bay

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

Frequently asked questions

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 travelling 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.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 travellers 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 variety of attractions that showcase the natural beauty and cultural richness of the U.S. Virgin Islands. The stunning beaches, such as Chocolate Hole Beach and the nearby Cruz Bay Beach, are great for sunbathing, swimming, and snorkelling. The vibrant Cruz Bay area offers charming shops, restaurants, and bars, making it a great spot for dining and enjoying local cuisine.Additionally, the Virgin Islands National Park, accessible from Cruz Bay, features breathtaking hiking trails that lead to spectacular views, historic sugar mill ruins, and pristine coastal scenery. For those interested in water activities, there are numerous opportunities for sailing, kayaking, and exploring the surrounding waters.
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 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 travellers 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 cosy cabin or a beach house, 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. 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

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