Estate Chocolate Hole and Great Cruz Bay holiday rentals

We found 3,491 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Estate Chocolate Hole and Great Cruz Bay by choosing from 54 houses, 83 flats and other holiday rentals. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

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

Showing deals for:11 Dec - 18 Dec

Private kitchen
Outdoor dining
Room
Private kitchen
Exceptional
(141 reviews)

Lameshur Cottage's Guest House

St. John

8% off
AU$3,221
for 7 nights, 1 cottage
AU$460 per night
includes taxes & fees
Lameshur Cottage's Guest House
Interior
Interior
Private kitchen
Room
Wonderful
(21 reviews)

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

St. Thomas

5% off
AU$1,930
for 7 nights, 1 villa
AU$276 per night
includes taxes & fees
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
Main level dining
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

8% off
AU$5,966
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
Property grounds
Terrace/patio
Exterior
Interior
Exceptional
(27 reviews)

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

St. John

7% off
AU$3,235
for 7 nights, 1 cottage
AU$462 per night
includes taxes & fees
Authentic Island Stay, Budget-Friendly Cottage, Peaceful Setting, Stunning Views
Dinette table east view to St. John.
Incredible view of Caribbean Sea.
Exterior
View of Caribbean Sea from the comfort of your bed. ☺️
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

9% off
AU$1,249
for 7 nights, 1 home
AU$178 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Approach to the house - plenty of parking.
Our coconut tree. We have seen giant barracuda, eagle rays, sting rays, turtles
Dining
Interior
Exceptional
(36 reviews)

SPECIAL PRICING! !!

St. Thomas

8% off
AU$6,265
for 7 nights, 1 villa
AU$895 per night
includes taxes & fees
SPECIAL PRICING! !!
Interior
Property grounds
Pool
Private kitchen
Exceptional
(113 reviews)

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

St. John

9% off
AU$3,602
for 7 nights, 1 villa
AU$515 per night
includes taxes & fees
“Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”
Terrace/patio
Pool
Private kitchen
Room
Exceptional
(47 reviews)

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

St. John

5% off
AU$4,086
for 7 nights, 1 home
AU$584 per night
includes taxes & fees
Breathtaking Panoramic Views of the British Virgin Islands from hot tub & pool!
Another view from the kitchen window.
Sandy Spit - One of the many daytrip locations availble with a boat rental.
Pool
It's always sunny at Watergate Villas unit 1610
Exceptional
(62 reviews)

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

St. Thomas

7% off
AU$2,893
for 7 nights, 1 apartment
AU$413 per night
includes taxes & fees
READ MY REVIEWS! Vacation in style right on the ocean ABSOLUTELY THE BEST!
Living area
Dining
Property grounds
Interior
Exceptional
(14 reviews)

Seaside Blue <br>Hosted by Shilpi Singh

St. Thomas

8% off
AU$1,943
for 7 nights, 1 apartment
AU$278 per night
includes taxes & fees
Seaside Blue <br>Hosted by Shilpi Singh
Room
Down Island View!
Bathroom
Ocean View from your deck
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

8% off
AU$5,264
for 7 nights, 1 apartment
AU$752 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Living room
Porch
Exterior
Backyard
Exceptional
(11 reviews)

Modern St. John USVI Villa Ocean Views King Suite 7 Min to Cruz Bay

St. John

8% off
AU$7,727
for 7 nights, 1 home
AU$1,104 per night
includes taxes & fees
Modern St. John USVI Villa Ocean Views King Suite 7 Min to Cruz Bay
Living area
Dining
Pool
Interior
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
AU$2,438
for 7 nights, 1 apartment
AU$348 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
Kitchen
Ahhh...
Pool side dining
Entrance
Exceptional
(152 reviews)

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

St. Thomas

8% off
AU$9,355
for 7 nights, 1 villa
AU$1,336 per night
includes taxes & fees
Private Paradise! One level, panoramic views from every room!
Bedroom
From the balcony
Overlooking the ocean
Fully equipped kitchen
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

8% off
AU$3,696
for 7 nights, 1 apartment
AU$528 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Private kitchen
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

8% off
AU$7,874
for 7 nights, 1 home
AU$1,125 per night
includes taxes & fees
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
Interior
Property grounds
Private kitchen
Pool
Exceptional
(9 reviews)

Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!

St. Thomas

7% off
AU$2,858
for 7 nights, 1 apartment
AU$408 per night
includes taxes & fees
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
Exterior
Property grounds
Villa from the pond in kayak
Property grounds
Exceptional
(18 reviews)

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

St. John

9% off
AU$4,493
for 7 nights, 1 villa
AU$642 per night
includes taxes & fees
"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.
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

8% off
AU$5,773
for 7 nights, 1 apartment
AU$825 per night
includes taxes & fees
5★ SAPPHIRE SUNRISE-2 Story Direct Ocean Beachfront Villa- Luxe Reno!
Cook with an ocean view! Gourmet kitchen is equipped with everything you need
Large covered verandah-perfect place to enjoy morning coffee and dinner
Queen bedroom (3rd bedroom of the villa) with A/C
The entrance to your private villa is surrounded by lush gardens
Exceptional
(90 reviews)

Villa Capiz: Luxury Hilltop Villa with Pool, Jacuzzi and Panoramic Ocean Views

St. John

8% off
AU$11,399
for 7 nights, 1 villa
AU$1,628 per night
includes taxes & fees
Villa Capiz: Luxury Hilltop Villa with Pool, Jacuzzi and Panoramic Ocean Views
British Virgin Islands in the distance. Bring your passport!!!!
Overlook in St John. Just a short ferry ride away from the condo
Dining for 4. Invite your friends for dinner and cocktails.
View of main pool located in front of our onsite restaurant, Sudis
Exceptional
(14 reviews)

Welcome To YOUR CARIBBEAN DREAM

St. Thomas

8% off
AU$2,348
for 7 nights, 1 apartment
AU$335 per night
includes taxes & fees
Welcome To YOUR CARIBBEAN DREAM
Newly furnished and freshly painted studio right on the ocean.
View from patio never gets old...you hear the waves at all times.
Swimming in the pool and listening to the waves...the perfect relaxing afternoon
Private kitchen
Exceptional
(30 reviews)

CHECK OUT THE VIEW! Fantastic Affordable Oceanfront Studio - Listen to the Waves

St. Thomas

7% off
AU$1,801
for 7 nights, 1 apartment
AU$257 per night
includes taxes & fees
CHECK OUT THE VIEW! Fantastic Affordable Oceanfront Studio - Listen to the Waves
Terrace/patio
Exterior
Living area
Property grounds
Exceptional
(20 reviews)

Home with panoramic views with access to private beach!

St. Thomas

8% off
AU$17,566
for 7 nights, 1 villa
AU$2,509 per night
includes taxes & fees
Home with panoramic views with access to private beach!
California King bed
Balcony view with direct views of marina, St John’s , and BVIs.
The Sapphire Village complex.
Living area
Exceptional
(38 reviews)

Beachtime! Top Floor End Unit Studio Overlooking Marina!

St. Thomas

8% off
AU$2,493
for 7 nights, 1 apartment
AU$356 per night
includes taxes & fees
Beachtime! Top Floor End Unit Studio Overlooking Marina!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday 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 holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday 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

Are you hoping to find attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Estate Chocolate Hole and Great Cruz Bay a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 an adventurous traveller or just want to appreciate the scenery, Estate Chocolate Hole and Great Cruz Bay is a great place to get out in nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport 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 centre. If you can't find a flight that works for your travel itinerary, you might consider flying into St. Thomas (STT-Cyril E. King), which is 12.4 mi (19.9 km) away.

Frequently asked questions

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.
Are all fees included in the Estate Chocolate Hole and Great Cruz Bay holiday homes prices shown on Stayz?
Stayz 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.
Are there any Estate Chocolate Hole and Great Cruz Bay holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Estate Chocolate Hole and Great Cruz Bay holiday homes?
You can find great discounts on holiday homes in Estate Chocolate Hole and Great Cruz Bay on Stayz, 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 change or cancel my Estate Chocolate Hole and Great Cruz Bay holiday home booking on Stayz?
To find Estate Chocolate Hole and Great Cruz Bay holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Estate Chocolate Hole and Great Cruz Bay?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Estate Chocolate Hole and Great Cruz Bay holiday home?
Book your Estate Chocolate Hole and Great Cruz Bay holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Estate Chocolate Hole and Great Cruz Bay?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Estate Chocolate Hole and Great Cruz Bay to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.