Estate Chocolate Hole and Great Cruz Bay holiday lettings

We found 3,450 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

Pathway to the airstream 😎
Incredible view of Caribbean Sea.
Dinette table east view to St. John.
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
£663
for 7 nights, 1 home
£95 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Ocean View from your deck
Down Island View!
Kitchen/Dining
Room
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

7% off
£2,877
for 7 nights, 1 apartment
£411 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Interior
Pool
Outdoor dining
Dining
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

7% off
£2,225
for 7 nights, 1 apartment
£318 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
Living area
Dining
Room
Interior
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
£1,367
for 7 nights, 1 apartment
£195 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
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
Socially distant beach bar food menu and pickup area
Exceptional
(65 reviews)

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

St. Thomas

9% off
£2,040
for 7 nights, 1 apartment
£291 per night
includes taxes & fees
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
Interior
Exterior
Living area
Terrace/patio
Exceptional
(20 reviews)

Home with panoramic views with access to private beach!

St. Thomas

8% off
£10,091
for 7 nights, 1 villa
£1,442 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

8% off
£2,176
for 7 nights, 1 apartment
£311 per night
includes taxes & fees
Seaside Charm!! Cozy BEACHFRONT Condo located on Sapphire Beach steps to thesand
Parking right outside your front door, shaded place to sit and relax.
View of the mountains from your bed!
Exterior
Private kitchen
Exceptional
(37 reviews)

Island Escape for Two, Class and Comfort

St. John

8% off
£1,289
for 7 nights, 1 apartment
£184 per night
includes taxes & fees
Island Escape for Two, Class and Comfort
Bedroom
From the balcony
Hummingbirds flock these flowers
Overlooking the ocean
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

8% off
£1,975
for 7 nights, 1 apartment
£282 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Pool
Property grounds
Interior
Dining
Exceptional
(9 reviews)

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

St. Thomas

7% off
£1,504
for 7 nights, 1 apartment
£215 per night
includes taxes & fees
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
Dining
Property grounds
Living area
Room
Exceptional
(12 reviews)

Beautiful Villa on Point Pleasant Resort

St. Thomas

8% off
£4,183
for 7 nights, 1 villa
£598 per night
includes taxes & fees
Beautiful Villa on Point Pleasant Resort
The Sapphire Village complex.
Balcony view with direct views of marina, St John’s , and BVIs.
Living area
Kitchen area has all appliances needed for in house meals.
Exceptional
(38 reviews)

Beachtime! Top Floor End Unit Studio Overlooking Marina!

St. Thomas

7% off
£1,232
for 7 nights, 1 apartment
£176 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
(135 reviews)

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

St. Thomas

8% off
£2,391
for 7 nights, 1 apartment
£342 per night
includes taxes & fees
5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
Bedroom
The Pool
Gorgeous Sapphire beach resort.
Exterior
Exceptional
(13 reviews)

Sapphire Beach Resort Rental

St. Thomas

20% off
£3,089
for 7 nights, 1 apartment
£441 per night
includes taxes & fees
Sapphire Beach Resort Rental
Private kitchen
Living area
Interior
Pool
Exceptional
(101 reviews)

Sapphire Dominica-Gorgeous View Walk to beach

St. Thomas

7% off
£1,549
for 7 nights, 1 apartment
£221 per night
includes taxes & fees
Sapphire Dominica-Gorgeous View Walk to beach
Extra seating!
Property grounds
and more seating for additional family/friends
Complex Pool
Exceptional
(30 reviews)

Immerse Yourself in Luxury at our breathtaking beachfront Condo!

St. Thomas

8% off
£4,097
for 7 nights, 1 apartment
£585 per night
includes taxes & fees
Immerse Yourself in Luxury at our breathtaking beachfront Condo!
Master bedroom
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
Living area with 49” SONY SmartTV and great WIFI for all your Netflix, Hulu, etc
Exceptional
(25 reviews)

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

St. Thomas

7% off
£1,568
for 7 nights, 1 apartment
£224 per night
includes taxes & fees
FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !
Beach Bar
Pool
Lobby
2nd floor sofa bed.
Exceptional
(191 reviews)

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

St. Thomas

8% off
£2,032
for 7 nights, 1 apartment
£290 per night
includes taxes & fees
Corner Villa with Stunning Sapphire Bay Views – Sleeps 6 w/Backup Generator.
Private kitchen
Interior
Interior
Aerial view
Excellent
(20 reviews)

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

St. Thomas

5% off
£993
for 7 nights, 1 villa
£142 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
(151 reviews)

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

St. Thomas

8% off
£2,807
for 7 nights, 1 apartment
£401 per night
includes taxes & fees
5 ★ “Sapphire SeaView” - Direct Ocean Front at Sapphire Beach Resort & Marina
Living area
Pool
Room
Outdoor dining
Exceptional
(5 reviews)

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

St. Thomas

8% off
£2,209
for 7 nights, 1 apartment
£316 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, 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

How much does it cost to rent a holiday home in Estate Chocolate Hole And Great Cruz Bay?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Estate Chocolate Hole And Great Cruz Bay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Estate Chocolate Hole And Great Cruz Bay holiday house rentals?
You can find great discounts on house rentals in Estate Chocolate Hole And Great Cruz Bay on Vrbo, 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 find long-stay holiday rentals in Estate Chocolate Hole And Great Cruz Bay?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Estate Chocolate Hole And Great Cruz Bay holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
How early should I book a Estate Chocolate Hole And Great Cruz Bay holiday rental?
Book your Estate Chocolate Hole And Great Cruz Bay holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Estate Chocolate Hole And Great Cruz Bay home rental booking on Vrbo?
To find Estate Chocolate Hole And Great Cruz Bay holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Estate Chocolate Hole And Great Cruz Bay holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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