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Estate Chocolate Hole and Great Cruz Bay Vacation Rentals

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Vacation Rentals in Estate Chocolate Hole and Great Cruz Bay

BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
Smart TV
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
10.0 out of 10, Exceptional, (14)
"Beautiful well-appointed new villa on the beach in Chocolate Hole. They are still building the villas, so it is a bit of a construction zone and can be a little hard to find. (You turn onto a gravel road that looks like it goes nowhere but actually circles around to the villas. This one is the back on the left, second one in. We had a bit of trouble finding it - finally found it by comparing deck furniture to the photos in the listing!) Gorgeous inside - new appliances & furniture, beautifully...
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
Pool
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
9.6 out of 10, Exceptional, (13)
"Everything was perfect. Hard to leave that pool! Close to anything and everything. Clean, cozy, would return 100x"
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
Poi Pu St John - Great Views & Total Privacy
Pool
Poi Pu St John - Great Views & Total Privacy
9.8 out of 10, Exceptional, (68)
"We had an awesome time in St. John, and. Poi Pu villa was in a great location. Only 5 mins to Cruz Bay, we explored all the surrounding neighborhoods on foot, gaining beautiful vantage points of the island around every corner. A few days of our week stay (July) were incredibly hot so the dipping pool and rooms with AC were key. We learned to time our outings with the scheduled power outages in the PMs. We couldn’t quite figure out how to keep the open air living and kitchen mosquito free, but...
Poi Pu St John - Great Views & Total Privacy
Hilltop Villas at Bluebeard's Castle by Capital Vacations
Aerial view
Hilltop Villas at Bluebeard's Castle by Capital Vacations
3.0 star property
8.6 out of 10, Excellent, (1321)
"Shaun at the front desk started our weekend off with excellent customer service. Tevind was there to pick us up like VIP and take us to the front desk. Our view of the city and bay was amazing day and night. Our rooms were clean and had everything we needed. Don’t hesitate this is a landmark site. "
The price is $221
includes taxes & fees
$197 per night
Oct 8 - Oct 9
Hilltop Villas at Bluebeard's Castle by Capital Vacations
Secret Harbour Beach Resort
On the beach, white sand, sun loungers, beach umbrellas
Secret Harbour Beach Resort
4.0 star property
8.8 out of 10, Excellent, (1255)
"View is breathtaking. The beach and water was incredible. Room are very clean and inviting. Love the design (relaxing). The onsite restaurants were very expensive and the service does not meet the pricing. Bar was also expensive and the drinks were not will made and of poor quality. "
The price is $459
includes taxes & fees
$412 per night
Sep 25 - Sep 26
Secret Harbour Beach Resort
Castle Villas at Bluebeard's by Capital Vacations
View from property
Castle Villas at Bluebeard's by Capital Vacations
2.5 star property
8.4 out of 10, Very Good, (873)
"The view was incredible. Everything was fine."
The price is $214
includes taxes & fees
$190 per night
Sep 29 - Sep 30
Castle Villas at Bluebeard's by Capital Vacations
Flamboyan on the Bay Resort and Villas
Premium Studio | Terrace/patio
Flamboyan on the Bay Resort and Villas
3.5 star property
8.8 out of 10, Excellent, (486)
"The property has a wonderful view of the ocean and the rooms are beautifully appointed and clean. The bar/restaurant on premises had great food. And having a place to grab breakfast was also convenient."
The price is $126
includes taxes & fees
$113 per night
Sep 30 - Oct 1
Flamboyan on the Bay Resort and Villas
Pirates Pension at Bluebeard's Castle by Capital Vacations
Exterior
Pirates Pension at Bluebeard's Castle by Capital Vacations
3.0 star property
8.4 out of 10, Very Good, (594)
"Couldn’t have asked for a better stay! The room and balcony views were amazing. The staff were friendly. For those who may have physically incapabilities, please be mindful that this property is very hilly with steps on top of steps to the lobby, your room, the restaurant etc. I highly recommend if you want an affordable property with great views and close proximity to everything. Renting a car is the best thing!!"
The price is $192
includes taxes & fees
$171 per night
Oct 2 - Oct 3
Pirates Pension at Bluebeard's Castle by Capital Vacations
Marriott's Frenchman's Cove
Exterior
Marriott's Frenchman's Cove
4.0 star property
9.0 out of 10, Wonderful, (166)
"Everything was nice"
The price is $708
includes taxes & fees
$629 per night
Sep 26 - Sep 27
Marriott's Frenchman's Cove
Sapphire Beach Resort
On the beach, scuba diving, snorkeling, beach volleyball
Sapphire Beach Resort
3.0 star property
6.8 out of 10, (248)
"Check in was a nightmare as we could not get into our room and it took over 1 hour to locate someone to bring the key - this after we pre arranged for a later than expected check in as our flight was delayed - once that was settled the property is very nice, bar, restaurant, beach was excellent and a great location just 3 minutes from red hook"
Sapphire Beach Resort
Beachfront Villas at Crystal Cove
On the beach, white sand, sun loungers, beach towels
Beachfront Villas at Crystal Cove
4.0 star property
9.4 out of 10, Exceptional, (106)
"nice"
Beachfront Villas at Crystal Cove
Virgin Islands Campground
Beach nearby, white sand, sun loungers, beach umbrellas
Virgin Islands Campground
2.0 star property
9.4 out of 10, Exceptional, (111)
"Excellent place to stay! "
Virgin Islands Campground
Gallows Point Resort
Exterior
Gallows Point Resort
4.0 star property
9.6 out of 10, Exceptional, (492)
"We loved the property. The staff was outstanding and the grounds and accommodations were immaculate. We will definitely go back again. There is a restaurant that offers takeout. Cruz bay is close enough to walk, but there is a hill to come back up on the return. The shuttle will pick you up and bring you back to the ferry but no transportation otherwise. There is parking for a rental "
Gallows Point Resort
Private Paradise! One level, panoramic views from every room!
Property grounds
Private Paradise! One level, panoramic views from every room!
10.0 out of 10, Exceptional, (120)
"I'm hesitant to write this review because the property, location, and vacation were so perfect, I almost don't want anyone else to know about it so I can book it again without worry that it may be unavailable! Everything was just as advertised and better. The beach is a couple miles from the house, and yes, it's worth it to rent a jeep. We had the beach to ourselves for the majority of the time. It really felt surreal. We used the coolers and snorkel gear in the house and that made it...
Private Paradise! One level, panoramic views from every room!
Sapphire Village Resort by Antilles Resorts
Aerial view
Sapphire Village Resort by Antilles Resorts
3.0 star property
6.2 out of 10, (297)
"Feel like home ambient"
Sapphire Village Resort by Antilles Resorts
Premium Oceanfront Sapphire Beach Resort & Marina
Pool
Premium Oceanfront Sapphire Beach Resort & Marina
9.8 out of 10, Exceptional, (13)
"Very good to work with "
The price is $323
includes taxes & fees
$290 per night
Sep 25 - Sep 26
Premium Oceanfront Sapphire Beach Resort & Marina
Blue Moon Villa At Point Pleasant Resort Studio Condo by RedAwning
Condo, 1 Bedroom | Property grounds
Blue Moon Villa At Point Pleasant Resort Studio Condo by RedAwning
3.0 star property
Blue Moon Villa At Point Pleasant Resort Studio Condo by RedAwning
Suite St. John at Gallows Point Resort
View from property
Suite St. John at Gallows Point Resort
4.0 star property
8.8 out of 10, Excellent, (88)
"Great view."
The price is $741
includes taxes & fees
$677 per night
Sep 27 - Sep 28
Suite St. John at Gallows Point Resort
Gorgeous Condo At Sapphire on St Thomas. Walk-in Level. Killer Island Views!
Pool
Gorgeous Condo At Sapphire on St Thomas. Walk-in Level. Killer Island Views!
9.4 out of 10, Exceptional, (74)
"Beautiful view, comfortable bed, property manager very helpful. Pillows weren’t very comfortable one of our only complaints. Other similar units we stayed in provided Tommy Bahama beach chairs and a cooler. These things would’ve been very nice to have. Keypad lock was finicky but figured it out. Had a great week staying here!"
Gorgeous Condo At Sapphire on St Thomas. Walk-in Level. Killer Island Views!
New listing! Easy walk to 3 separate Beaches, Pool, and multiple Restaurants!
Beach nearby, sun loungers, beach towels
New listing! Easy walk to 3 separate Beaches, Pool, and multiple Restaurants!
9.6 out of 10, Exceptional, (25)
"The place was very clean and well taken care of, we had a great time and all the property is very nice as well, no hot tub like the ad said but the pool was amazing "
New listing! Easy walk to 3 separate Beaches, Pool, and multiple Restaurants!
Don't see what you're looking for?
See all available properties in Estate Chocolate Hole and Great Cruz Bay
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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Other types of properties in Estate Chocolate Hole and Great Cruz Bay you may be interested in

The Westin St. John Resort Villas
Outdoor pool
The Westin St. John Resort Villas
4.5 star property
8.2 out of 10, Very Good, (380)
"The place was well maintained, clean. The pool and lounge areas were clean. It was too pricey overall and the staff were not so friendly. Haven’t been on this island before so no comparators."
The price is $468
includes taxes & fees
$416 per night
Oct 7 - Oct 8
The Westin St. John Resort Villas
New rental, Newly Renovated/2 ensuites/open main room/beautiful view/large pool
Pool
New rental, Newly Renovated/2 ensuites/open main room/beautiful view/large pool
2.0 star property
New rental, Newly Renovated/2 ensuites/open main room/beautiful view/large pool
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
Smart TV
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
10.0 out of 10, Exceptional, (14)
"Beautiful well-appointed new villa on the beach in Chocolate Hole. They are still building the villas, so it is a bit of a construction zone and can be a little hard to find. (You turn onto a gravel road that looks like it goes nowhere but actually circles around to the villas. This one is the back on the left, second one in. We had a bit of trouble finding it - finally found it by comparing deck furniture to the photos in the listing!) Gorgeous inside - new appliances & furniture, beautifully...
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
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.

Frequently asked questions

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

Yes, we have vacation rentals near well known points of interest in Estate Chocolate Hole and Great Cruz Bay, or you can go with a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Estate Chocolate Hole and Great Cruz Bay?

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!: Visitors like this Estate Chocolate Hole and Great Cruz Bay vacation home rental. It is located on the beach and has a balcony, a private yard, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker. Our travelers also rate Poi Pu St John - Great Views & Total Privacy as a favorite home for rent in Estate Chocolate Hole and Great Cruz Bay.

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

Choose from 47 Expedia vacation rentals in Estate Chocolate Hole and Great Cruz Bay for a memorable vacation.

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

Great Cruz Bay and Chocolate Hole Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Chocolate Hole and Sunset Beach are other places worth a visit.

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

A vacation rental is a private property where you can stay for several days or longer in Estate Chocolate Hole and Great Cruz Bay. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.