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

Estate Chocolate Hole and Great Cruz Bay Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (507 reviews)
"Unfortunately, the pool was under construction during our stay and unusable, but we didn't allow that to stop us. The beach was quite and relaxing, thus Westin has a family vibe and good for children. The staff was friendly. I do think they can do better at advertising the water and children's activities. The rooms were excellent and resturants too. Ferry service and crew were great too. Great stay for a family of 5!"
United States
Shani
The price is AU$555
includes taxes & fees
7 Oct - 8 Oct
The Westin St. John Resort Villas
A beach with clear turquoise water, white sand, and rocky outcrops.

2. Luxury Villa w/ Private Pool, Game Room, Outdoor Kitchen, Panoramic Ocean Views

Luxury Villa w/ Private Pool, Game Room, Outdoor Kitchen, Panoramic Ocean Views
Cruz Bay
10.0 out of 10, Exceptional, (1 review)
"Amazing views and a nice place to relax."
United States
Jeremy F.
Luxury Villa w/ Private Pool, Game Room, Outdoor Kitchen, Panoramic Ocean Views
A beach with turquoise water, sandy shore, and distant mountains.

3. Flamingo Grove Glamping Site with AC

Flamingo Grove Glamping Site with AC
St John
9.8 out of 10, Exceptional, (30 reviews)
"Really enjoyed our stay. We felt well taken care of and loved the location!"
United States
John
The price is AU$258
includes taxes & fees
30 Sept - 1 Oct
Flamingo Grove Glamping Site with AC
A restaurant with outdoor seating, palm trees, and a mountain in the background.

4. Octopus Den Glamping Site with AC

Octopus Den Glamping Site with AC
St John
10.0 out of 10, Exceptional, (8 reviews)
"Great for a short stay!"
United States
Kimberly J.
The price is AU$258
includes taxes & fees
30 Sept - 1 Oct
Octopus Den Glamping Site with AC
A beach with turquoise water, sandy shore, and distant mountains.

5. Turtle Nest Family Glamping Site with AC

Turtle Nest Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful property and a fun experience! Would stay again."
United States
Carlee D.
The price is AU$400
includes taxes & fees
27 Sept - 28 Sept
Turtle Nest Family Glamping Site with AC
A coastal landscape with a beach, clear blue waters, and lush greenery.

6. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (41 reviews)
"View was amazing . Unit itself was very unique"
United States
Zach Ezekiel Azurus
The price is AU$727
includes taxes & fees
11 Oct - 12 Oct
Villa Island Paradise
A wooden chair and table set against a lush green backdrop with a view of a valley and distant buildings.

7. Quiet cozy studio 5 minute drive from Cruz Bay

Quiet cozy studio 5 minute drive from Cruz Bay
St John
9.6 out of 10, Exceptional, (84 reviews)
"The host was great! She helped with some last minute reservation changes. This place was clean, the beds were comfy and it was close to everything. We appreciated the beach chairs and cooler for the beaches. We would stay here again!"
United States
Ashley
Quiet cozy studio 5 minute drive from Cruz Bay
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 AU$278
includes taxes & fees
27 Sept - 28 Sept
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

9. Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
St Thomas
9.6 out of 10, Exceptional, (174 reviews)
"Excellent location and very nice place to visit and Sudi's Bar/restaurant is the place to be and the whole staff is Excellent and the food is delicious and reminds you of Cheers 😎."
United States
Quincy
The price is AU$349
includes taxes & fees
26 Sept - 27 Sept
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
A room with a TV, wicker furniture, and a view of the ocean.

10. 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 AU$1,033
includes taxes & fees
2 Oct - 3 Oct
Suite St. John at Gallows Point Resort
A beach with clear turquoise water, a sandy shore, and a distant island with buildings.

11. Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
St. Thomas
9.6 out of 10, Exceptional, (201 reviews)
"We LOVED our stay and would recommend it to anyone going to St. Thomas. The location was unbeatable, and the property was equipped with everything we needed and more!"
United States
Alessandra C.
The price is AU$278
includes taxes & fees
27 Sept - 28 Sept
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A clear turquoise sea with people swimming.

12. Breathtaking Views from Sapphire Village II

Breathtaking Views from Sapphire Village II
St Thomas
8.8 out of 10, Excellent, (40 reviews)
"The room was beautiful great View locations on point for everything you needed within the area the only downfall I would say was the hill if you're walking and if you have any type of handicap but other than that beautiful place to stay"
United States
Jason
The price is AU$397
includes taxes & fees
25 Sept - 26 Sept
Breathtaking Views from Sapphire Village II
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

13. 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, (243 reviews)
"Stayed for two and had a great time. Location was close to many tourist spots, hiking, shopping, and entertainments."
United States
Dede C.
The price is AU$337
includes taxes & fees
27 Sept - 28 Sept
The Captain and the Mermaid - Adventures in Paradise are waiting!
A beach with turquoise water, sandy shore, and distant mountains.

14. 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 AU$532
includes taxes & fees
13 Oct - 14 Oct
Lameshur Cottage's Guest House
A beach with clear turquoise water, sandy shore, and buildings in the background.

15. Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
St. Thomas
9.8 out of 10, Exceptional, (142 reviews)
"We had an amazing stay, the condo was very clean and close to several beaches and restaurants."
United States
Jessica D.
The price is AU$417
includes taxes & fees
25 Sept - 26 Sept
Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
A beach with clear turquoise water, sandy shore, and buildings in the background.

16. 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 AU$337
includes taxes & fees
27 Sept - 28 Sept
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
A balcony with a round table and chairs, a potted plant, and a view of a sunset over a body of water.

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

Sunset Hideaway Suite - Oceanview/central to Cruz Bay
St John
9.8 out of 10, Exceptional, (19 reviews)
"Clean and spacious! Great location, proximity to Cruz Bay!"
United States
Laina M.
The price is AU$567
includes taxes & fees
25 Sept - 26 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.

18. 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 AU$1,043
includes taxes & fees
27 Sept - 28 Sept
St. John Escape 4-304
A balcony with wicker chairs and a small table, overlooking a turquoise sea with boats and a hilly landscape.

19. Aahana Studio 4-303S

Aahana Studio 4-303S
Cruz Bay, St. John
10.0 out of 10, Exceptional, (60 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 AU$814
includes taxes & fees
25 Sept - 26 Sept
Aahana Studio 4-303S
A beach with palm trees, clear blue sky, and a calm sea.

20. 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 AU$331
includes taxes & fees
27 Sept - 28 Sept
Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
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

4 bedroom, 4 bathroom. Private Pool, Ocean views. Chocolate Hole, Cruz Bay.

4 bedroom, 4 bathroom. Private Pool, Ocean views. Chocolate Hole, Cruz Bay.

10/10 Excellent
"Everything was great.The only request is to please provide a backup generator. We lost power for 16 hrs and no backup generator. With 10People 2 being babies 1,3 and 2 being 73 and 72. It was a pretty rough go with no running water, no toilets and no a/c. Other thank that the management ladies are amazing and Ricki the cab driver was definitely the highlights. ThankYou for an amazing week."
Danny M. 7-night trip
Posted 6 days ago
4 bedroom, 4 bathroom. Private Pool, Ocean views. Chocolate Hole, Cruz Bay.

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 favourite 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 depend 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 AU$321 per night. Entering your travel dates in the search wizard might find you 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 • Pool • Incredible Views • In-House Car Rental: 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 Private Pool overlooking ocean, large deck on Estate Property. Great Privacy. and Poi Pu St John - Great Views, Total Privacy & Tesla Solar Backup System.

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. While here, Chocolate Hole Beach and Rendezvous Bay are other places worth a visit.

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.