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
Property grounds
Private kitchen
Exceptional
(141 reviews)

Lameshur Cottage's Guest House

St. John

8% off
AU$3,195
for 7 nights, 1 cottage
AU$456 per night
includes taxes & fees
Lameshur Cottage's Guest House
Private kitchen
Interior
Room
Aerial view
Wonderful
(21 reviews)

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

St. Thomas

5% off
AU$1,914
for 7 nights, 1 villa
AU$273 per night
includes taxes & fees
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
Main level dining
Outdoor entertainment area
Main level living room
Patio off main level
Exceptional
(44 reviews)

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

St. Thomas

8% off
AU$5,918
for 7 nights, 1 home
AU$845 per night
includes taxes & fees
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
Dining
Our coconut tree. We have seen giant barracuda, eagle rays, sting rays, turtles
Interior
Approach to the house - plenty of parking.
Exceptional
(36 reviews)

SPECIAL PRICING! !!

St. Thomas

8% off
AU$6,215
for 7 nights, 1 villa
AU$888 per night
includes taxes & fees
SPECIAL PRICING! !!
Interior
Terrace/patio
Room
Property grounds
Exceptional
(27 reviews)

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

St. John

7% off
AU$3,209
for 7 nights, 1 cottage
AU$458 per night
includes taxes & fees
Authentic Island Stay, Budget-Friendly Cottage, Peaceful Setting, Stunning Views
Pool
Property grounds
Private kitchen
Interior
Exceptional
(113 reviews)

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

St. John

9% off
AU$3,572
for 7 nights, 1 villa
AU$510 per night
includes taxes & fees
“Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”
Exterior
Incredible view of Caribbean Sea.
View of Caribbean Sea from the comfort of your bed. ☺️
Pathway to the airstream 😎
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

9% off
AU$1,239
for 7 nights, 1 home
AU$177 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Terrace/patio
Pool
Room
Property grounds
Exceptional
(47 reviews)

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

St. John

5% off
AU$4,053
for 7 nights, 1 home
AU$579 per night
includes taxes & fees
Breathtaking Panoramic Views of the British Virgin Islands from hot tub & pool!
Bathroom
Down Island View!
Ocean View from your deck
Kitchen/Dining
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

8% off
AU$5,222
for 7 nights, 1 apartment
AU$746 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Another view from the kitchen window.
Sandy Spit - One of the many daytrip locations availble with a boat rental.
Pool
Master bedroom sliding door to patio and amazing view
Exceptional
(62 reviews)

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

St. Thomas

7% off
AU$2,869
for 7 nights, 1 apartment
AU$410 per night
includes taxes & fees
READ MY REVIEWS! Vacation in style right on the ocean ABSOLUTELY THE BEST!
Interior
Dining
Pool
Room
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
AU$2,392
for 7 nights, 1 apartment
AU$342 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
Living area
Dining
Interior
Private kitchen
Exceptional
(14 reviews)

Seaside Blue <br>Hosted by Shilpi Singh

St. Thomas

8% off
AU$1,927
for 7 nights, 1 apartment
AU$275 per night
includes taxes & fees
Seaside Blue <br>Hosted by Shilpi Singh
Entrance
Ahhh...
Pool side dining
Kitchen
Exceptional
(152 reviews)

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

St. Thomas

8% off
AU$9,279
for 7 nights, 1 villa
AU$1,326 per night
includes taxes & fees
Private Paradise! One level, panoramic views from every room!
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$7,810
for 7 nights, 1 home
AU$1,116 per night
includes taxes & fees
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
Overlooking the ocean
From the balcony
Bedroom
Hummingbirds flock these flowers
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

8% off
AU$3,666
for 7 nights, 1 apartment
AU$524 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Property grounds
Property grounds
Exterior
Private kitchen
Exceptional
(18 reviews)

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

St. John

9% off
AU$4,456
for 7 nights, 1 villa
AU$637 per night
includes taxes & fees
"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.
Dining
Property grounds
Private kitchen
Pool
Exceptional
(9 reviews)

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

St. Thomas

7% off
AU$2,834
for 7 nights, 1 apartment
AU$405 per night
includes taxes & fees
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
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$5,726
for 7 nights, 1 apartment
AU$818 per night
includes taxes & fees
5★ SAPPHIRE SUNRISE-2 Story Direct Ocean Beachfront Villa- Luxe Reno!
British Virgin Islands in the distance. Bring your passport!!!!
Overlook in St John. Just a short ferry ride away from the condo
Balcony overlooking the marina
Dining for 4. Invite your friends for dinner and cocktails.
Exceptional
(14 reviews)

Welcome To YOUR CARIBBEAN DREAM

St. Thomas

8% off
AU$2,329
for 7 nights, 1 apartment
AU$333 per night
includes taxes & fees
Welcome To YOUR CARIBBEAN DREAM
Private kitchen
View from patio never gets old...you hear the waves at all times.
Newly furnished and freshly painted studio right on the ocean.
Swimming in the pool and listening to the waves...the perfect relaxing afternoon
Exceptional
(30 reviews)

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

St. Thomas

7% off
AU$1,787
for 7 nights, 1 apartment
AU$255 per night
includes taxes & fees
CHECK OUT THE VIEW! Fantastic Affordable Oceanfront Studio - Listen to the Waves
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

9% off
AU$4,062
for 7 nights, 1 apartment
AU$580 per night
includes taxes & fees
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
Private kitchen
Pool
Dining
Outdoor dining
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

8% off
AU$4,184
for 7 nights, 1 apartment
AU$598 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
Living area
Balcony view with direct views of marina, St John’s , and BVIs.
California King bed
The Sapphire Village complex.
Exceptional
(38 reviews)

Beachtime! Top Floor End Unit Studio Overlooking Marina!

St. Thomas

8% off
AU$2,473
for 7 nights, 1 apartment
AU$353 per night
includes taxes & fees
Beachtime! Top Floor End Unit Studio Overlooking Marina!
Room
Welcome to Seaglass!
Sunrise at our marina.
Internet TV with over 20,000 stations, 30,000 songs, Netflix, ESPN and more!
Exceptional
(120 reviews)

Gorgeous Condo At Sapphire on St Thomas. Walk-in Level. Killer Island Views!

St. Thomas

7% off
AU$1,916
for 7 nights, 1 apartment
AU$274 per night
includes taxes & fees
Gorgeous Condo At Sapphire on St Thomas. Walk-in Level. Killer Island Views!

  • 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.