Estate Chocolate Hole and Great Cruz Bay holiday rentals

We found 3,460 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 56 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:20 Nov - 27 Nov

Dining table
Deck at night
Pool at night (Old pool look)
Room
Exceptional
(70 reviews)

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

St. Thomas

8% off
S$7,229
for 7 nights, 1 home
S$1,033 per night
includes taxes & fees
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
View of Caribbean Sea from the comfort of your bed. ☺️
Incredible view of Caribbean Sea.
Pathway to the airstream 😎
Exterior
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

9% off
S$1,144
for 7 nights, 1 home
S$163 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Ocean View from your deck
Down Island View!
Bathroom
Room
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

7% off
S$4,945
for 7 nights, 1 apartment
S$706 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Dining
Pool
Outdoor dining
Private kitchen
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

7% off
S$3,980
for 7 nights, 1 apartment
S$569 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
Room
Dining
Living area
Interior
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
S$2,488
for 7 nights, 1 apartment
S$355 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
The Beach Bar with live music and grill on the property
Pool
Socially distant beach bar food menu and pickup area
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$3,648
for 7 nights, 1 apartment
S$521 per night
includes taxes & fees
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
Property grounds
Exterior
Interior
Terrace/patio
Exceptional
(20 reviews)

Home with panoramic views with access to private beach!

St. Thomas

8% off
S$16,925
for 7 nights, 1 villa
S$2,418 per night
includes taxes & fees
Home with panoramic views with access to private beach!
Lovely view of the complex and beach
View from condo
Complex pool
Bonus living space equipped with a sofa bed
Exceptional
(23 reviews)

Seaside Charm!! Cozy BEACHFRONT Condo located on Sapphire Beach steps to thesand

St. Thomas

7% off
S$3,880
for 7 nights, 1 apartment
S$554 per night
includes taxes & fees
Seaside Charm!! Cozy BEACHFRONT Condo located on Sapphire Beach steps to thesand
Exterior
View of the mountains from your bed!
Parking right outside your front door, shaded place to sit and relax.
Private kitchen
Exceptional
(37 reviews)

Island Escape for Two, Class and Comfort

St. John

8% off
S$2,249
for 7 nights, 1 apartment
S$321 per night
includes taxes & fees
Island Escape for Two, Class and Comfort
Fully equipped kitchen
From the balcony
Overlooking the ocean
Hummingbirds flock these flowers
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

7% off
S$3,488
for 7 nights, 1 apartment
S$498 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Pool
Property grounds
Dining
Private kitchen
Exceptional
(9 reviews)

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

St. Thomas

7% off
S$2,664
for 7 nights, 1 apartment
S$381 per night
includes taxes & fees
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
Living area
Property grounds
Private kitchen
Room
Exceptional
(12 reviews)

Beautiful Villa on Point Pleasant Resort

St. Thomas

8% off
S$7,121
for 7 nights, 1 villa
S$1,017 per night
includes taxes & fees
Beautiful Villa on Point Pleasant Resort
 California King bed
Balcony view with direct views of marina, St John’s , and BVIs.
The Sapphire Village complex.
Kitchen area has all appliances needed for in house meals.
Exceptional
(38 reviews)

Beachtime! Top Floor End Unit Studio Overlooking Marina!

St. Thomas

8% off
S$2,086
for 7 nights, 1 apartment
S$298 per night
includes taxes & fees
Beachtime! Top Floor End Unit Studio Overlooking Marina!
Room
Our Actual Balcony and View of the Amazing Sapphire Beach Marina!
A casually elegant space to enjoy your time at the beach! Photos from Sept 2022!
Apple TV, Netflix App, DVD/BlueRay with movies & 50MB Fiber Internet!
Exceptional
(134 reviews)

5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!

St. Thomas

8% off
S$4,266
for 7 nights, 1 apartment
S$609 per night
includes taxes & fees
5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
Gorgeous Sapphire beach resort.
The Pool
Exterior
Bedroom
Exceptional
(13 reviews)

Sapphire Beach Resort Rental

St. Thomas

20% off
S$5,300
for 7 nights, 1 apartment
S$757 per night
includes taxes & fees
Sapphire Beach Resort Rental
Interior
Living area
Pool
Private kitchen
Exceptional
(101 reviews)

Sapphire Dominica-Gorgeous View Walk to beach

St. Thomas

7% off
S$2,731
for 7 nights, 1 apartment
S$390 per night
includes taxes & fees
Sapphire Dominica-Gorgeous View Walk to beach
and more seating for additional family/friends
Property grounds
Main living area
Complex Pool
Exceptional
(30 reviews)

Immerse Yourself in Luxury at our breathtaking beachfront Condo!

St. Thomas

8% off
S$7,010
for 7 nights, 1 apartment
S$1,001 per night
includes taxes & fees
Immerse Yourself in Luxury at our breathtaking beachfront Condo!
Living area with 49” SONY SmartTV and great WIFI for all your Netflix, Hulu, etc
The tranquil sound of the waves is ever present.  You just can’t beat the view.
Fully equipped kitchen with brand new fridge, microwave, and all cookware
Master bedroom
Exceptional
(25 reviews)

FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !

St. Thomas

7% off
S$2,755
for 7 nights, 1 apartment
S$394 per night
includes taxes & fees
FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !
Lobby
Pool
Bar (on property)
Beach Bar
Exceptional
(191 reviews)

Corner Villa with Stunning Sapphire Bay Views – Sleeps 6 w/Backup Generator.

St. Thomas

8% off
S$3,597
for 7 nights, 1 apartment
S$514 per night
includes taxes & fees
Corner Villa with Stunning Sapphire Bay Views – Sleeps 6 w/Backup Generator.
Private kitchen
Interior
Room
Interior
Excellent
(20 reviews)

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

St. Thomas

5% off
S$1,737
for 7 nights, 1 villa
S$248 per night
includes taxes & fees
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
Interior
Romantic Luxury with Endless Sapphire Beach Ocean Views in St Thomas Paradise!
Relax your days and evenings away here - can 't you hear the waves already?
Living area
Exceptional
(150 reviews)

5 ★ “Sapphire SeaView” - Direct Ocean Front at Sapphire Beach Resort & Marina

St. Thomas

8% off
S$4,851
for 7 nights, 1 apartment
S$693 per night
includes taxes & fees
5 ★ “Sapphire SeaView” - Direct Ocean Front at Sapphire Beach Resort & Marina
Room
Pool
Living area
Exterior detail
Exceptional
(5 reviews)

Changes in Latitude 18.3 spacious Mahogany Run condo with ocean views.

St. Thomas

8% off
S$3,947
for 7 nights, 1 apartment
S$564 per night
includes taxes & fees
Changes in Latitude 18.3 spacious Mahogany Run condo with ocean 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. 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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