Estate Chocolate Hole and Great Cruz Bay Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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, (512 reviews)
"Everything was amazing! It will always be my go to when I come to visit."
United States
Treacy
The price is AU$641
includes taxes & fees
22 Nov - 23 Nov
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.
The price is AU$3,160
includes taxes & fees
29 Nov - 30 Nov
Luxury Villa w/ Private Pool, Game Room, Outdoor Kitchen, Panoramic Ocean Views
A coastal landscape with a beach, clear blue waters, and lush greenery.

3. 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$818
includes taxes & fees
9 Nov - 10 Nov
Villa Island Paradise
A beach with clear turquoise water, trees, and a sandy shore.

4. Beachfront Villas at Crystal Cove

Beachfront Villas at Crystal Cove
4.0 star property
St. Thomas
9.6 out of 10, Exceptional, (179 reviews)
"We had great 8 days at this property. We are so happy with our stay. We got everything we need for wonderful vacation. Location is excellent, villa very clean and staffed with everything and has a lot of extras."
United States
Olena
The price is AU$738
includes taxes & fees
25 Nov - 26 Nov
Beachfront Villas at Crystal Cove
A room with a TV, wicker furniture, and a view of the ocean.

5. 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$1,070
includes taxes & fees
9 Nov - 10 Nov
Suite St. John at Gallows Point Resort
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

6. 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, (258 reviews)
"We had an amazing time. It's highly recommended"
United States
Camierre
The price is AU$402
includes taxes & fees
14 Nov - 15 Nov
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

7. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (957 reviews)
"All around great place"
United States
Hector
The price is AU$376
includes taxes & fees
23 Nov - 24 Nov
Bluebeard's Castle Resort
A balcony with a round table and chairs, a potted plant, and a view of a sunset over a body of water.

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

Sunset Hideaway Suite - Oceanview/central to Cruz Bay
St John
9.8 out of 10, Exceptional, (20 reviews)
"Clean and spacious! Great location, proximity to Cruz Bay!"
United States
Laina M.
The price is AU$567
includes taxes & fees
16 Nov - 17 Nov
Sunset Hideaway Suite - Oceanview/central to Cruz Bay
A beach with clear turquoise water, a sandy shore, and a distant island with buildings.

9. 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, (203 reviews)
"Great place to stay and peaceful"
United States
Candice D.
The price is AU$402
includes taxes & fees
13 Nov - 14 Nov
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A beach with clear turquoise water and waves.

10. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (164 reviews)
"Great spot and excellent host"
United States
amanda c.
The price is AU$385
includes taxes & fees
9 Nov - 10 Nov
The Mermaid's Pearl at Sapphire Beach
A clear turquoise sea with people swimming.

11. 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$431
includes taxes & fees
9 Nov - 10 Nov
Breathtaking Views from Sapphire Village II
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

12. 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, (246 reviews)
"Great clean and safe place to stay"
United States
angela C.
The price is AU$335
includes taxes & fees
10 Nov - 11 Nov
The Captain and the Mermaid - Adventures in Paradise are waiting!
A beach with palm trees, sun loungers, and a building in the background.

13. Sapphire Beachside walkout condo E 106

Sapphire Beachside walkout condo E 106
St Thomas
10.0 out of 10, Exceptional, (101 reviews)
"Great location"
United States
Jacqueline
The price is AU$776
includes taxes & fees
9 Nov - 10 Nov
Sapphire Beachside walkout condo E 106
A beach with clear turquoise water, palm trees, and a sandy shore.

14. Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated

Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated
St John
10.0 out of 10, Exceptional, (326 reviews)
"The property was close to everything. Perfect spot. People at the front lobby were wonderful. Would most certainly stay there again and recommend."
United States
Bob
The price is AU$1,122
includes taxes & fees
25 Nov - 26 Nov
Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

15. 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
9.8 out of 10, Exceptional, (208 reviews)
"Greetings from St Thomas Capitol of the United States Virgin Islands. 90 Days Residency Required to become a United States Virgin Islands Citizen. USVI 5% IRS Corporate Tax rate on All World-Wide income without City or State Taxes just Open a Headquarters Expedia....."
United States
Kevin
The price is AU$492
includes taxes & fees
22 Nov - 23 Nov
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
A beach with clear turquoise water, sandy shore, and buildings in the background.

16. 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, (144 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$437
includes taxes & fees
9 Nov - 10 Nov
Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
A beach with palm trees, clear blue sky, and a calm sea.

17. 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, (97 reviews)
"Safire Condos and beach are great. Host were amazing, promptly responding to any messages. Short 5 minute walk to one of the best beaches, clean, not crowded, and outstanding food and drink options."
United States
Chamberlain
The price is AU$348
includes taxes & fees
9 Nov - 10 Nov
Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
A beach with clear turquoise water, a sandy shore, and a distant view of a small island with buildings and vegetation.

18. Updated: Luxe Condo steps from Sapphire Beach!

Updated: Luxe Condo steps from Sapphire Beach!
St Thomas
9.6 out of 10, Exceptional, (100 reviews)
"Initially, somewhat tough to locate specific condo within the condo complex. Overall nice property. Very comfortable bed. Very close to Sapphire beach, Lindquist beach, and Red Hook. I would definitely stay again."
United States
Christopher
The price is AU$382
includes taxes & fees
26 Nov - 27 Nov
Updated: Luxe Condo steps from Sapphire Beach!
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, (61 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$1,039
includes taxes & fees
19 Nov - 20 Nov
Aahana Studio 4-303S
A swimming pool with steps leading into it, a patio area with outdoor furniture, and a view of the outdoors.

20. Luxury Private Pool Villa. Grill. Generator@Sapphire

Luxury Private Pool Villa. Grill. Generator@Sapphire
Red Hook
9.6 out of 10, Exceptional, (19 reviews)
"Had a great stay, will definitely be back!"
United States
Madison C.
The price is AU$683
includes taxes & fees
26 Nov - 27 Nov
Luxury Private Pool Villa. Grill. Generator@Sapphire
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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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$335 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?

Private Pool overlooking ocean, large deck on Estate Property. Great Privacy.: This highly rated holiday home rental in Estate Chocolate Hole and Great Cruz Bay is located by the ocean, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games. Some other homes for rent in Estate Chocolate Hole and Great Cruz Bay include Secluded Oceanfront Villa • Pool • Incredible Views • In-House Car Rental 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.