Estate Chocolate Hole and Great Cruz Bay holiday rentals

We found 3,494 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
Private kitchen
Room
Exceptional
(141 reviews)

Lameshur Cottage's Guest House

St. John

8% off
AU$3,194
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 living room
Outdoor entertainment area
Property grounds
Patio off main level
Exceptional
(44 reviews)

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

St. Thomas

8% off
AU$5,917
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
Approach to the house - plenty of parking.
Interior
Exceptional
(36 reviews)

SPECIAL PRICING! !!

St. Thomas

8% off
AU$6,214
for 7 nights, 1 villa
AU$888 per night
includes taxes & fees
SPECIAL PRICING! !!
Room
Terrace/patio
Exterior
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
garden entrance
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.
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

9% off
AU$1,238
for 7 nights, 1 home
AU$177 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Private kitchen
Pool
Property grounds
Room
Exceptional
(47 reviews)

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

St. John

5% off
AU$4,052
for 7 nights, 1 home
AU$579 per night
includes taxes & fees
Breathtaking Panoramic Views of the British Virgin Islands from hot tub & pool!
Kitchen/Dining
Down Island View!
Room
Bathroom
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

8% off
AU$5,221
for 7 nights, 1 apartment
AU$746 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Master bedroom sliding door to patio and amazing view
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$2,869
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
Living area
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
AU$2,440
for 7 nights, 1 apartment
AU$349 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
Private kitchen
Dining
Living area
Property grounds
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...
Abi Beach below-beach bar and restaurant
Pool side dining
Exceptional
(152 reviews)

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

St. Thomas

8% off
AU$9,278
for 7 nights, 1 villa
AU$1,325 per night
includes taxes & fees
Private Paradise! One level, panoramic views from every room!
Room
Deck at night
Private kitchen
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
Hummingbirds flock these flowers
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$3,665
for 7 nights, 1 apartment
AU$524 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Private kitchen
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$4,456
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
Interior
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$5,725
for 7 nights, 1 apartment
AU$818 per night
includes taxes & fees
5★ SAPPHIRE SUNRISE-2 Story Direct Ocean Beachfront Villa- Luxe Reno!
Balcony overlooking the marina
Overlook in St John. Just a short ferry ride away from the condo
View of main pool located in front of our onsite restaurant, Sudis
British Virgin Islands in the distance. Bring your passport!!!!
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
Newly furnished and freshly painted studio right on the ocean.
View from patio never gets old...you hear the waves at all times.
View from patio
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
Interior
Pool
Dining
Outdoor dining
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

8% off
AU$4,183
for 7 nights, 1 apartment
AU$598 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
The Beach Bar with live music and grill on the property
Pool
Socially distancing beach bar area for taking a drink or lunch to the beach
The patio and beach right in front of you!
Exceptional
(65 reviews)

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

St. Thomas

9% off
AU$4,061
for 7 nights, 1 apartment
AU$580 per night
includes taxes & fees
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
Living area
Balcony view with direct views of marina, St John’s , and BVIs.
The Sapphire Village complex.
 California King bed
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!
Well equipped for anyone who loves to cook -- or eat!
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 is the most popular type of holiday home accommodation in Estate Chocolate Hole and Great Cruz Bay?
The most in-demand types of holiday homes in Estate Chocolate Hole and Great Cruz Bay are villas. Hoping for something different? Stayz has many options to match the unique needs of our guests, so you'll see holiday homes in all sizes and shapes. The perfect fit is ready and waiting for you — discover yours today.
How much does it cost to rent a holiday home in Estate Chocolate Hole and Great Cruz Bay?
The average price for a holiday home in Estate Chocolate Hole and Great Cruz Bay is determined by several factors, such as property type, length of stay and season. Whether you're in search of a sprawling villa with space for extended family or a cosy cabin ideal for just you and the kids, just add your travel dates to find stays with exceptional value.
How much does it cost to rent a beach house in Estate Chocolate Hole and Great Cruz Bay?
Prices for beach houses in Estate Chocolate Hole and Great Cruz Bay can differ depending on the size and style of the property and when you're travelling. Simply enter your dates of travel into Stayz and the number of guests to view your home options and prices. From there you can use our filters to narrow your search results by ratings, amenities, nearby activities and more.
Are there pet-friendly holiday homes in Estate Chocolate Hole and Great Cruz Bay?
Yes, there are. You can choose from 310 holiday homes that allow pets in Estate Chocolate Hole and Great Cruz Bay. Several of our pet-friendly holiday homes even have an outdoor space for your furry friend to play around in, complimentary treats, special dog beds and proximity to parks. Apply the "Pets allowed" filter to find your place on Stayz.
Can I rent a house with a pool in Estate Chocolate Hole and Great Cruz Bay?
Add an extra layer of fun to your holiday by booking one of the 270 houses with a private pool in Estate Chocolate Hole and Great Cruz Bay. Use our search filter to find properties with pools on Stayz, then spend leisurely days splashing and playing in a swimming pool that's all yours.
What are popular home amenities in Estate Chocolate Hole and Great Cruz Bay?
A fireplace, a swimming pool and ski-in/ski-out facilities head the list of most popular home amenities in Estate Chocolate Hole and Great Cruz Bay. Whether you're heading away solo, with your sweetheart or a group of dear friends, Stayz can help you find a holiday home that matches your style with all the options you need.
Are there large group holiday homes in Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay has 58 holiday homes that can fit 10 or more guests. These stays come with plenty of space to share good times with family and friends.
Are there holiday homes in Estate Chocolate Hole and Great Cruz Bay that welcome kids?
Estate Chocolate Hole and Great Cruz Bay has 307 family-friendly holiday homes to pick from. And finding a stay that welcomes kids is a cinch with Stayz's "Properties good for families" filter. Besides having the whole place to yourselves, you'll enjoy access to conveniences and perks like extra bedrooms, full kitchens and private pools.
What are the top attractions for families in Estate Chocolate Hole and Great Cruz Bay?
Keep the kids amused at these fun family-friendly attractions in Estate Chocolate Hole and Great Cruz Bay:
  • Trunk Bay
  • Cruz Bay Beach
  • Honeymoon Beach
Are there one-bedroom holiday homes in Estate Chocolate Hole and Great Cruz Bay?
You can pick from 42 one-bedroom homes in Estate Chocolate Hole and Great Cruz Bay. Whether you're on the lookout for a cosy cottage or a condo, Stayz's one-bedroom properties are perfect if you don't need huge amounts of space. One of the best things about having your own pad? You won't ever need to share your adventure with strangers.
Can I find two-bedroom holiday homes in Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay has 124 two-bedroom holiday properties for you to pick from. Book a holiday home with all the privacy and comfort you're looking for at a price that won't break the bank on Stayz.
Are there holiday homes with WiFi in Estate Chocolate Hole and Great Cruz Bay?
Take your pick of 60 holiday homes with WiFi in Estate Chocolate Hole and Great Cruz Bay. If you want to disconnect from the world on your escape, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay has 294 holiday homes where you can relax and recharge in air-conditioned comfort. To book a stay on Stayz that features this amenity, choose your travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Estate Chocolate Hole and Great Cruz Bay?
The minimum age is generally 16, 18 or 21. It can differ across properties on Stayz, so look at the rules of your chosen Estate Chocolate Hole and Great Cruz Bay stay before booking.
How long can I rent a holiday home in Estate Chocolate Hole and Great Cruz Bay for?
The amount of time you can book an Estate Chocolate Hole and Great Cruz Bay holiday home for depends on each property. Simply tap in your travel dates to see options that offer long-term stays. They have all you need to make your extended getaway more comfortable and convenient, like air conditioning and kitchens. Some properties may also offer discounted weekly or monthly prices, so you can stay longer for less money.