A coastal town with buildings, a harbor filled with boats, and a mountainous backdrop.

Estate Chocolate Hole and Great Cruz Bay Holiday Rentals

Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Estate Chocolate Hole and Great Cruz Bay holiday rentals

A resort with a central pool, palm trees, and a view of the ocean.

1. The Westin St. John Resort Villas

The Westin St. John Resort Villas
4.5 star property
St. John
8.4 out of 10, Very good, (504 reviews)
"We had a good stay at the Westin in St. John. Service is slow in the resort other than that everything else was good."
United States
Rituparna
The price is NZ$668
includes taxes & fees
15 Sept - 16 Sept
The Westin St. John Resort Villas
A tropical beach with clear turquoise waters, white sand, and lush greenery.

2. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (38 reviews)
"Such an amazing place to stay at St. Johns. Very clean, comfortable and cool. Balcony was exceptional and they had snorkeling gear which was so cool! Will definitely return. This was our 2nd time at st . John's"
United States
Angelo
The price is NZ$867
includes taxes & fees
6 Sept - 7 Sept
Villa Island Paradise
A room with a TV, wicker furniture, and a view of the ocean.

3. Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort
4.0 star property
St. John
8.8 out of 10, Excellent, (106 reviews)
"Friendly staff. Beautiful property."
United States
Sean
The price is NZ$1,242
includes taxes & fees
7 Sept - 8 Sept
Suite St. John at Gallows Point Resort
A wooden chair and table set against a lush green backdrop with a view of a valley and distant buildings.

4. Cozy Island Studio-5 Mins to Cruz Bay & Beaches

Cozy Island Studio-5 Mins to Cruz Bay & Beaches
St John
9.6 out of 10, Exceptional, (82 reviews)
"Amazing host and great property!"
United States
Stephanie K.
The price is NZ$396
includes taxes & fees
3 Sept - 4 Sept
Cozy Island Studio-5 Mins to Cruz Bay & Beaches
A balcony with a round table and chairs, a potted plant, and a view of a sunset over a body of water.

5. Sunset Hideaway Suite - Oceanview/central to Cruz Bay

Sunset Hideaway Suite - Oceanview/central to Cruz Bay
St John
9.8 out of 10, Exceptional, (18 reviews)
"Clean and spacious! Great location, proximity to Cruz Bay!"
United States
Laina M.
The price is NZ$695
includes taxes & fees
15 Sept - 16 Sept
Sunset Hideaway Suite - Oceanview/central to Cruz Bay
A covered outdoor area with a table and chairs, a view of the sea, and potted plants.

6. St. John Escape 4-304

St. John Escape 4-304
St. John
10.0 out of 10, Exceptional, (130 reviews)
"We had a wonderful time staying in this beautiful property while visiting St John! "
United States
Kari H.
The price is NZ$1,250
includes taxes & fees
2 Sept - 3 Sept
St. John Escape 4-304
A coastal resort with multiple buildings, a swimming pool, and boats in the background.

7. Sunset Ridge Villas Unit D

Sunset Ridge Villas Unit D
3.5 star property
St. John
9.4 out of 10, Exceptional, (3 reviews)
"This property was excellent especially for us a family of 4 with teenage kids. The space was great and the location was easy enough to get to. The amenities were excellent, from a fully outfitted kitchen to great beach resources such as chairs, cooler & snorkel equipment. "
United States
Jessica
The price is NZ$1,062
includes taxes & fees
5 Sept - 6 Sept
Sunset Ridge Villas Unit D
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

8. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
St. Thomas
9.4 out of 10, Exceptional, (254 reviews)
"Enjoyed our stay "
United States
Jason A.
The price is NZ$388
includes taxes & fees
10 Sept - 11 Sept
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
A balcony with wicker chairs and a small table, overlooking a turquoise sea with boats and a hilly landscape.

9. Aahana Studio 4-303S

Aahana Studio 4-303S
Cruz Bay, St. John
10.0 out of 10, Exceptional, (58 reviews)
"Very clean. Great location. Helpful property manager. Great value for the money. Good sunset views. Very convenient to restaurants!"
United States
Charlene Z.
The price is NZ$976
includes taxes & fees
4 Sept - 5 Sept
Aahana Studio 4-303S
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

10. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (789 reviews)
"Beautiful property our family loved our stay here"
United States
Tricia
The price is NZ$386
includes taxes & fees
30 Sept - 1 Oct
Bluebeard's Castle Resort
A beach with turquoise water, sandy shore, and distant mountains.

11. Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (141 reviews)
"Amazing place! Great host!!Close to Salt Pond."
United States
Shawn C.
The price is NZ$591
includes taxes & fees
3 Sept - 4 Sept
Lameshur Cottage's Guest House
A clear turquoise sea with a palm tree and a swing hanging over the water.

12. Amazing St. John Paradise most comfortable and convenient accommodations

Amazing St. John Paradise most comfortable and convenient accommodations
St John
10.0 out of 10, Exceptional, (99 reviews)
"Great condo and location. Have used this unit multiple times and it works great for us."
United States
Brady J.
The price is NZ$1,340
includes taxes & fees
23 Sept - 24 Sept
Amazing St. John Paradise most comfortable and convenient accommodations
A beach with clear turquoise water, sandy shore, and buildings in the background.

13. Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
St Thomas
9.8 out of 10, Exceptional, (128 reviews)
"Great place. I stay here two times a year. Always consistent. Always clean."
United States
John H.
The price is NZ$400
includes taxes & fees
3 Sept - 4 Sept
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
A coastal view with boats, palm trees, and a grassy area with chairs and tables.

14. Gallows Point 12A

Gallows Point 12A
Cruz Bay
9.6 out of 10, Exceptional, (9 reviews)
"This place was amazing! Super easy check in, friendly accommodations, and just an amazing experience! "
United States
Jason F.
The price is NZ$1,100
includes taxes & fees
12 Sept - 13 Sept
Gallows Point 12A
A marina with multiple boats docked, surrounded by multi-story buildings with balconies.

15. Blue Chair Bliss 1-102S

Blue Chair Bliss 1-102S
St. John
10.0 out of 10, Exceptional, (9 reviews)
"The unit we rented was perfect. Great location and the room had everything we needed for our trip. Will definitely be renting this on our next trip back."
United States
Edward E.
The price is NZ$1,175
includes taxes & fees
12 Sept - 13 Sept
Blue Chair Bliss 1-102S
A coastal resort with multiple buildings, a marina, and clear turquoise waters.

16. Breathtaking Views from Sapphire Village

Breathtaking Views from Sapphire Village
ST THOMAS
9.4 out of 10, Exceptional, (114 reviews)
"Great place to stay for the night."
United States
Kyle E.
The price is NZ$516
includes taxes & fees
2 Sept - 3 Sept
Breathtaking Views from Sapphire Village
Clear turquoise sea water with waves at the shore.

17. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (163 reviews)
"The Mermaid’s Pearl was a comfortable fit for my son (19) and me. It is located in a quiet complex with a beautiful view from the balcony. The studio is a perfect size for two people and was very clean. We enjoyed the local restaurant (Sudi’s) and the pool just outside the front door, as well as the short walk to the Safire Beach complex (local coffee shop and eateries on the beach). We also walked into Red Hook which took about 20 minutes. Red Hook is small but has plenty of little shops and...
United States
Melissa
The price is NZ$447
includes taxes & fees
2 Sept - 3 Sept
The Mermaid's Pearl at Sapphire Beach
A marina with multiple boats docked, a clear blue sky, and a distant view of a mountainous landscape.

18. NEW LISTING!!! Renovated Charming Studio Retreat with Stunning Caribbean Views

NEW LISTING!!! Renovated Charming Studio Retreat with Stunning Caribbean Views
St Thomas
9.8 out of 10, Exceptional, (22 reviews)
"it was excellent!"
United States
Sam F.
The price is NZ$514
includes taxes & fees
4 Sept - 5 Sept
NEW LISTING!!! Renovated Charming Studio Retreat with Stunning Caribbean Views
A beach with palm trees, clear blue sky, and a calm sea.

19. Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312

Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
St Thomas
9.6 out of 10, Exceptional, (96 reviews)
"Great location! The beach chairs and cooler were a nice bonus. The resort has a nice pool -- small, but clean and with several chairs and a restroom/changing room. Would definitely stay here again. "
United States
Steph M.
The price is NZ$400
includes taxes & fees
8 Sept - 9 Sept
Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

20. The Captain and the Mermaid - Adventures in Paradise are waiting!

The Captain and the Mermaid - Adventures in Paradise are waiting!
St Thomas
9.8 out of 10, Exceptional, (237 reviews)
"Great location. "
United States
Carolyn W.
The price is NZ$412
includes taxes & fees
3 Sept - 4 Sept
The Captain and the Mermaid - Adventures in Paradise are waiting!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Estate Chocolate Hole and Great Cruz Bay Hotel Reviews

Villa Catalina, great views, private pool, full generator, AC, Last minute deals

Villa Catalina, great views, private pool, full generator, AC, Last minute deals

10/10 Excellent
"Was a wonderful property and everything was handled super professionally. Five stars!"
Paul C. 7-night trip
Posted 9 days ago
Villa Catalina, great views, private pool, full generator, AC, Last minute deals

Find out more about Estate Chocolate Hole and Great Cruz Bay

Everything you need to know about Estate Chocolate Hole and Great Cruz Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Estate Chocolate Hole and Great Cruz Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Estate Chocolate Hole and Great Cruz Bay holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Estate Chocolate Hole and Great Cruz Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Estate Chocolate Hole and Great Cruz Bay. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Estate Chocolate Hole and Great Cruz Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Estate Chocolate Hole and Great Cruz Bay holiday rentals we have selected for you start as low as NZ$386 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Estate Chocolate Hole and Great Cruz Bay rentals

At Expedia, we put the best Estate Chocolate Hole and Great Cruz Bay holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Estate Chocolate Hole and Great Cruz Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Estate Chocolate Hole and Great Cruz Bay holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Estate Chocolate Hole and Great Cruz Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Estate Chocolate Hole and Great Cruz Bay?

Yes, there are holiday rentals close to the most popular sights in Estate Chocolate Hole and Great Cruz Bay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Estate Chocolate Hole and Great Cruz Bay has to offer?

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!: This highly rated holiday home rental in Estate Chocolate Hole and Great Cruz Bay is located on the beach, and has a balcony, a private garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker. Some other homes for rent in Estate Chocolate Hole and Great Cruz Bay include Poi Pu St John - Great Views, Total Privacy & Tesla Solar Backup System and Private Pool overlooking ocean, large deck on Estate Property. Great Privacy..

How many holiday rentals are there in Estate Chocolate Hole and Great Cruz Bay?

Choose from 54 Expedia holiday rentals in Estate Chocolate Hole and Great Cruz Bay for a memorable holiday.

What can I see and do in Estate Chocolate Hole and Great Cruz Bay?

Chocolate Hole and Great Cruz Bay are a couple of lovely local spots to get outside and enjoy nature. Trunk Bay and Virgin Islands National Park are other popular places to visit in the area.

What are holiday rentals like in Estate Chocolate Hole and Great Cruz Bay?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Estate Chocolate Hole and Great Cruz Bay. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips.