Estate Chocolate Hole and Great Cruz Bay holiday lettings

We found 3,474 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:27 Nov - 4 Dec

Interior
Our coconut tree. We have seen giant barracuda, eagle rays, sting rays, turtles
Living area
Approach to the house - plenty of parking.
Exceptional
(36 reviews)

SPECIAL PRICING! !!

St. Thomas

7% off
£3,386
for 7 nights, 1 villa
£484 per night
includes taxes & fees
SPECIAL PRICING! !!
Private kitchen
Outdoor dining
Room
Private kitchen
Exceptional
(141 reviews)

Lameshur Cottage's Guest House

St. John

6% off
£1,544
for 7 nights, 1 cottage
£221 per night
includes taxes & fees
Lameshur Cottage's Guest House
Dining table
Deck at night
Pool at night (Old pool look)
Private kitchen
Exceptional
(70 reviews)

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

St. Thomas

8% off
£4,327
for 7 nights, 1 home
£618 per night
includes taxes & fees
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
Pathway to the airstream 😎
Incredible view of Caribbean Sea.
View of Caribbean Sea from the comfort of your bed. ☺️
Exterior
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

8% 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!
Bathroom
Kitchen/Dining
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

7% off
£2,876
for 7 nights, 1 apartment
£411 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Pool- short walk from home. You can see pool from balcony.
Balcony View overlooks 3 bays- Great Cruz Bay- Westin, Hart Bay & Chocolate Hole
Bedroom 2 with Exterior Patio Acess
Living Room and Kitchen
Exceptional
(134 reviews)

TRANQUIL BREEZE [3 BR - 3 BA] Best Views & Location- Close to Town & Generator

St. John

7% off
£3,937
for 7 nights, 1 villa
£562 per night
includes taxes & fees
TRANQUIL BREEZE [3 BR - 3 BA] Best Views & Location- Close to Town & Generator
Pool
Sandy Spit - One of the many daytrip locations availble with a boat rental.
Another view from the kitchen window.
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
£1,551
for 7 nights, 1 apartment
£222 per night
includes taxes & fees
READ MY REVIEWS! Vacation in style right on the ocean ABSOLUTELY THE BEST!
Property grounds
Exterior
Living area
Interior
Exceptional
(20 reviews)

Home with panoramic views with access to private beach!

St. Thomas

8% off
£9,964
for 7 nights, 1 villa
£1,423 per night
includes taxes & fees
Home with panoramic views with access to private beach!
Socially distant beach bar food menu and pickup area
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
£2,092
for 7 nights, 1 apartment
£299 per night
includes taxes & fees
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
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
Dining for 4. Invite your friends for dinner and cocktails.
Exceptional
(14 reviews)

Welcome To YOUR CARIBBEAN DREAM

St. Thomas

8% off
£1,252
for 7 nights, 1 apartment
£179 per night
includes taxes & fees
Welcome To YOUR CARIBBEAN DREAM
Interior
Dining
Room
Pool
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
£1,320
for 7 nights, 1 apartment
£189 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
Pool
Property grounds
Interior
Private kitchen
Exceptional
(9 reviews)

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

St. Thomas

7% off
£1,503
for 7 nights, 1 apartment
£215 per night
includes taxes & fees
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
Private kitchen
View of the mountains from your bed!
King size custom made bed, with storage on all sides
Parking right outside your front door, shaded place to sit and relax.
Exceptional
(37 reviews)

Island Escape for Two, Class and Comfort

St. John

8% off
£1,354
for 7 nights, 1 apartment
£193 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

8% off
£1,974
for 7 nights, 1 apartment
£282 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Outdoor dining
Pool
Private kitchen
Interior
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

7% off
£2,224
for 7 nights, 1 apartment
£318 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
The Sapphire Village complex.
Balcony view with direct views of marina, St John’s , and BVIs.
California King bed
Living area
Exceptional
(38 reviews)

Beachtime! Top Floor End Unit Studio Overlooking Marina!

St. Thomas

7% off
£1,281
for 7 nights, 1 apartment
£183 per night
includes taxes & fees
Beachtime! Top Floor End Unit Studio Overlooking Marina!
Room
Property grounds
Living area
Private kitchen
Exceptional
(12 reviews)

Beautiful Villa on Point Pleasant Resort

St. Thomas

8% off
£4,181
for 7 nights, 1 villa
£597 per night
includes taxes & fees
Beautiful Villa on Point Pleasant Resort
Marina
Living area
Private kitchen
Pool
Exceptional
(101 reviews)

Sapphire Dominica-Gorgeous View Walk to beach

St. Thomas

7% off
£1,390
for 7 nights, 1 apartment
£199 per night
includes taxes & fees
Sapphire Dominica-Gorgeous View Walk to beach
Gorgeous outdoor deck on the sand!
The Pool
Gorgeous Sapphire beach resort.
Exterior
Exceptional
(13 reviews)

Sapphire Beach Resort Rental

St. Thomas

20% off
£3,088
for 7 nights, 1 apartment
£441 per night
includes taxes & fees
Sapphire Beach Resort Rental
Lobby
Pool
2nd floor sofa bed.
Beach Bar
Exceptional
(191 reviews)

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

St. Thomas

8% off
£2,031
for 7 nights, 1 apartment
£290 per night
includes taxes & fees
Corner Villa with Stunning Sapphire Bay Views – Sleeps 6 w/Backup Generator.
Interior
Interior
Aerial view
Private kitchen
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
Room
Pool
Exterior detail
Living area
Exceptional
(5 reviews)

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

St. Thomas

8% off
£2,208
for 7 nights, 1 apartment
£315 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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