Estate Chocolate Hole and Great Cruz Bay holiday rentals

We found 3,488 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, 84 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:4 Dec - 11 Dec

Patio off main level
Outdoor entertainment area
Main level living room
Property grounds
Exceptional
(44 reviews)

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

St. Thomas

7% off
S$5,557
for 7 nights, 1 home
S$794 per night
includes taxes & fees
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
Room
Interior
Aerial view
Private kitchen
Excellent
(20 reviews)

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

St. Thomas

5% off
S$1,753
for 7 nights, 1 villa
S$250 per night
includes taxes & fees
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
Approach to the house - plenty of parking.
Our coconut tree. We have seen giant barracuda, eagle rays, sting rays, turtles
Dining
Living area
Exceptional
(36 reviews)

SPECIAL PRICING! !!

St. Thomas

7% off
S$5,886
for 7 nights, 1 villa
S$841 per night
includes taxes & fees
SPECIAL PRICING! !!
Private kitchen
Property grounds
Interior
Pool
Exceptional
(112 reviews)

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

St. John

8% off
S$3,398
for 7 nights, 1 villa
S$485 per night
includes taxes & fees
“Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”
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
S$7,338
for 7 nights, 1 home
S$1,048 per night
includes taxes & fees
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
Pool side dining
Ahhh...
Abi Beach below-beach bar and restaurant
Entrance
Exceptional
(152 reviews)

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

St. Thomas

8% off
S$8,731
for 7 nights, 1 villa
S$1,247 per night
includes taxes & fees
Private Paradise! One level, panoramic views from every room!
Exterior
Incredible view of Caribbean Sea.
View of Caribbean Sea from the comfort of your bed. ☺️
Dinette table east view to St. John.
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

8% off
S$1,163
for 7 nights, 1 home
S$166 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
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
S$4,950
for 7 nights, 1 apartment
S$707 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Exterior
Property grounds
Private kitchen
Property grounds
Exceptional
(18 reviews)

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

St. John

9% off
S$4,238
for 7 nights, 1 villa
S$605 per night
includes taxes & fees
"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.
Living area
Dining
Interior
Property grounds
Exceptional
(14 reviews)

Seaside Blue <br>Hosted by Shilpi Singh

St. Thomas

8% off
S$1,778
for 7 nights, 1 apartment
S$254 per night
includes taxes & fees
Seaside Blue <br>Hosted by Shilpi Singh
Mimosas, anyone?
Welcome to our slice of paradise!
Evening Cocktails......can't beat that view!
Property grounds
Steps, literally steps, to the beautiful waters of the Caribbean
Exceptional
(11 reviews)

Carribean Sea Just Steps from Your Patio!!

St. Thomas

8% off
S$4,517
for 7 nights, 1 apartment
S$645 per night
includes taxes & fees
Carribean Sea Just Steps from Your Patio!!
It's always sunny at Watergate Villas unit 1610
Sandy Spit - One of the many daytrip locations availble with a boat rental.
Another view from the kitchen window.
Pool
Exceptional
(62 reviews)

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

St. Thomas

7% off
S$2,698
for 7 nights, 1 apartment
S$385 per night
includes taxes & fees
READ MY REVIEWS! Vacation in style right on the ocean ABSOLUTELY THE BEST!
Socially distancing beach bar area for taking a drink or lunch to the beach
Pool
The Beach Bar with live music and grill on the property
The patio and beach right in front of you!
Exceptional
(65 reviews)

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

St. Thomas

8% off
S$3,863
for 7 nights, 1 apartment
S$552 per night
includes taxes & fees
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
Interior
Exterior
Living area
Property grounds
Exceptional
(20 reviews)

Home with panoramic views with access to private beach!

St. Thomas

8% off
S$16,001
for 7 nights, 1 villa
S$2,286 per night
includes taxes & fees
Home with panoramic views with access to private beach!
Pool
Dining
Interior
Living area
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
S$2,472
for 7 nights, 1 apartment
S$353 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
View of main pool located in front of our onsite restaurant, Sudis
Overlook in St John. Just a short ferry ride away from the condo
Dining for 4. Invite your friends for dinner and cocktails.
British Virgin Islands in the distance. Bring your passport!!!!
Exceptional
(14 reviews)

Welcome To YOUR CARIBBEAN DREAM

St. Thomas

8% off
S$2,152
for 7 nights, 1 apartment
S$307 per night
includes taxes & fees
Welcome To YOUR CARIBBEAN DREAM
Private kitchen
Property grounds
Pool
Interior
Exceptional
(9 reviews)

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

St. Thomas

7% off
S$2,657
for 7 nights, 1 apartment
S$380 per night
includes taxes & fees
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
Outdoor dining
Pool
Private kitchen
Interior
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

7% off
S$3,930
for 7 nights, 1 apartment
S$561 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
Bedroom
From the balcony
Overlooking the ocean
Fully equipped kitchen
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

7% off
S$3,476
for 7 nights, 1 apartment
S$497 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
The entrance to your private villa is surrounded by lush gardens
Large covered verandah-perfect place to enjoy morning coffee and dinner
Bask in the Sun or Relax in the Shade of the Pergola
Cook with an ocean view! Gourmet kitchen is equipped with everything you need
Exceptional
(90 reviews)

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

St. John

8% off
S$10,327
for 7 nights, 1 villa
S$1,475 per night
includes taxes & fees
Villa Capiz: Luxury Hilltop Villa with Pool, Jacuzzi and Panoramic Ocean Views
Kitchen area has all appliances needed for in house meals.
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
S$2,316
for 7 nights, 1 apartment
S$331 per night
includes taxes & fees
Beachtime! Top Floor End Unit Studio Overlooking Marina!
Private kitchen
Living area
Pool
Marina
Exceptional
(101 reviews)

Sapphire Dominica-Gorgeous View Walk to beach

St. Thomas

7% off
S$2,290
for 7 nights, 1 apartment
S$327 per night
includes taxes & fees
Sapphire Dominica-Gorgeous View Walk to beach
Dining
Property grounds
Private kitchen
Living area
Exceptional
(12 reviews)

Beautiful Villa on Point Pleasant Resort

St. Thomas

8% off
S$7,088
for 7 nights, 1 villa
S$1,013 per night
includes taxes & fees
Beautiful Villa on Point Pleasant Resort
Gorgeous Sapphire beach resort.
The Pool
Exterior
Gorgeous outdoor deck on the sand!
Exceptional
(13 reviews)

Sapphire Beach Resort Rental

St. Thomas

20% off
S$5,298
for 7 nights, 1 apartment
S$757 per night
includes taxes & fees
Sapphire Beach Resort Rental
  • 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. Trunk Bay and Virgin Islands National Park are just a couple of the must-see attractions in the area. 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:

  • Trunk Bay (2.5 mi / 4.1 km)
  • Virgin Islands National Park (3 mi / 4.8 km)
  • 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)

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 rental accommodation in Estate Chocolate Hole and Great Cruz Bay?
The most in-demand types of holiday rentals in Estate Chocolate Hole and Great Cruz Bay are villas. Hoping for something different? Vrbo 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 rental in Estate Chocolate Hole and Great Cruz Bay?
The average price for a holiday rental 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 Vrbo and the number of guests to view your rental 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 rentals in Estate Chocolate Hole and Great Cruz Bay?
Yes, there are. You can choose from 310 holiday rentals that allow pets in Estate Chocolate Hole and Great Cruz Bay. Several of our pet-friendly holiday rentals 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 Vrbo.
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 Vrbo, then spend leisurely days splashing and playing in a swimming pool that's all yours.
What are popular rental 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 rental amenities in Estate Chocolate Hole and Great Cruz Bay. Whether you're heading away solo, with your sweetheart or a group of dear friends, Vrbo can help you find a holiday rental that matches your style with all the options you need.
Are there large group holiday rentals 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 rentals 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 Vrbo'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 rentals in Estate Chocolate Hole and Great Cruz Bay?
You can pick from 42 one-bedroom rentals in Estate Chocolate Hole and Great Cruz Bay. Whether you're on the lookout for a cosy cottage or a condo, Vrbo'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 rentals 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 Vrbo.
Are there holiday rentals with WiFi in Estate Chocolate Hole and Great Cruz Bay?
Take your pick of 60 holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay has 294 holiday rentals where you can relax and recharge in air-conditioned comfort. To book a stay on Vrbo 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 rental in Estate Chocolate Hole and Great Cruz Bay?
The minimum age is generally 16, 18 or 21. It can differ across properties on Vrbo, 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 rental 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.

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