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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, (13)
"Fantastic location in Chocolate Hole. The Villa itself is clean, bright, high-tech and furnished with high-end appliances and thoughtful detail, such as a Keurig cubby upstairs and robes in the closets. The villa is just Steps from a beach to snorkel. Our master bedroom was huge with high ceilings. The master bedroom balcony was spacious and provided a view of the bay. We played many card games at night and sipped coffee in the morning. Snorkel equipment and beach chairs are provided to use....
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, (10)
"We had an amazing stay at Villa Belvedere. Although the check in process didn’t go as smooth as we’d like, the rest of the stay was perfect. We originally coordinated with the property manager to meet us at the ferry dock but he did not show up or answer our calls which was very concerning. We eventually got in touch with him after picking up our Jeep rental and driving to the grocery store. Since it was about 3pm at this point the owner did remind us that check in was at 4pm so technically we...
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, (67)
"This is a great spot for a family or two couples. Small but well appointed with a fantastic outdoor space and great views. The pool was great with small kids and the hammock gets shade pretty much the whole day. Only a few minutes drive from Cruz Bay but far enough away to be quiet and secluded. There were beach chairs and some toys as well as a cooler to use which was fantastic. While we had a small issue with the water turning off, it was handled promptly and communication was excellent...
Poi Pu St John - Great Views & Total Privacy
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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, (1176)
"The staff was very helpful went above and beyond to assist us.I would definately recommend very relaxing."
The price is CA $282
CA $349 total
includes taxes & fees
Jul 2 - Jul 3
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, (1183)
"This was one of the best hotels I’ve stayed at. Stepped out onto the balcony, to get a gorgeous view of the beach, and hear the waves. Beautiful beach, chair, umbrella, towels, and bottled water. Great restaurant and shop!"
The price is CA $746
CA $922 total
includes taxes & fees
Jun 8 - Jun 9
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, (785)
"Our room was big, clean, and the property was safe. The morning Bartenders and staff at the restaurant was excellent. "
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, (423)
"We love that there's a wonderful restaurant and small coffeeshop available on property. The resort is only minutes from Magen's Bay."
The price is CA $176
CA $215 total
includes taxes & fees
Jun 9 - Jun 10
Flamboyan on the Bay Resort and Villas
Gallows Point Resort
Exterior
Gallows Point Resort
4.0 star property
9.6 out of 10, Exceptional, (472)
"What I liked most about this hotel is its location. It’s a quiet and safe property just outside of town and an easy walk to Cruz Bay."
Gallows Point Resort
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, (562)
"Love it"
The price is CA $312
CA $383 total
includes taxes & fees
Jun 9 - Jun 10
Pirates Pension at Bluebeard's Castle by Capital Vacations
Sapphire Beach Resort
On the beach, scuba diving, snorkeling, beach volleyball
Sapphire Beach Resort
3.0 star property
6.8 out of 10, (242)
"Weather was amazing...spent lots of time relaxing at the beach! The scenery was breathtaking. We met folks from various places across the U.S....frìendly and interesting! This experience is one that enhances our book of life's memories. "
Sapphire Beach Resort
Marriott's Frenchman's Cove
Exterior
Marriott's Frenchman's Cove
4.0 star property
9.0 out of 10, Wonderful, (159)
"Wonderful stay and friendly staff."
The price is CA $1,171
CA $1,317 total
includes taxes & fees
Jun 5 - Jun 6
Marriott's Frenchman's 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, (110)
"Had an excellent time! It was our first time camping and I am definitely more comfortable with showers and facilities rather than setting up a tent. The owners were excellent and the locals are so friendly! Highly recommend this place, but definitely bring industrial strength bug spray"
Virgin Islands Campground
Sapphire Village Resort by Antilles Resorts
Aerial view
Sapphire Village Resort by Antilles Resorts
3.0 star property
6.2 out of 10, (290)
"So I get to the resort and the taxi drops me off at the bar where i can chill and enjoThe beach The Bartender said if I show him my (hotel) email to register. I just took as he didn't know rude but whatever. Then he kept on insisting I show thim this email. I asked when is check in as (why are you busting my chops check in aint for 3 more hours) His response was I don't know when check in you may this you may that. I took this as a racist dog whistle. I took it he felt I didn't belong there....
Sapphire Village Resort by Antilles Resorts
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, (113)
"This villa is absolutely breathtaking! You feel as though you stepped right into dream with the gorgeous views! Every room is perfect and the property owners were the friendliest and most helpful we've ever had! We loved every minute of our stay in STT!"
Private Paradise! One level, panoramic views from every room!
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, (83)
"Amazing property and helpful staff. "
The price is CA $716
CA $1,045 total
includes taxes & fees
Jun 9 - Jun 10
Suite St. John at Gallows Point Resort
Sapphire Beach Villa
Panoramic Condo, 1 King Bed with Sofa bed, Sea View | Terrace/patio
Sapphire Beach Villa
3.5 star property
9.4 out of 10, Exceptional, (40)
"Sudi's was good and very comvenient."
Sapphire Beach Villa
Blue Moon Villa At Point Pleasant Resort 1 Bedroom Condo by RedAwning
Studio | Pool
Blue Moon Villa At Point Pleasant Resort 1 Bedroom Condo by RedAwning
3.0 star property
Blue Moon Villa At Point Pleasant Resort 1 Bedroom Condo by RedAwning
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, (101)
"Such a great experience upon arrival. Concierge, Gorety met us in the parking lot. She provided a tour of the property and was available if needed. The outside of the property may be a turn off due age and simply the weather can be tough on the exterior; however you open the door and this place was amazing - nice upgrades throughout. The walk to the beach is 2 min - take your coolers, backpack cooler if you have one. The restaurants have amazing food - from good ole burgers to Chilean Sea...
Beachfront Villas at Crystal Cove
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, (67)
"My daughter and I had the most wonderful stay. It was beautiful beyond words. The accommodations were clean and comfortable. The bed was super nice. We had to contact Andre when we first arrived and he answered and took care of us immediately. We ate at Sudi’s several times and I have to say they have the best shrimp tacos I have ever had. It was nice to have a restaurant so close that we could walk to it in a couple of minutes and not have to take a taxi somewhere. The snorkeling was amazing...
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!
9.4 out of 10, Exceptional, (21)
"Loved the pools,grounds,n room. The hot tub wasnt hot but I enjoyed my stay during Carnival Week! did"
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.

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, (366)
"Terrific service staff was super nice and property was clean. restaurants very nice but a bit pricey…after all it is an island!"
The price is CA $845
CA $951 total
includes taxes & fees
Jun 20 - Jun 21
The Westin St. John Resort Villas
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, (13)
"Fantastic location in Chocolate Hole. The Villa itself is clean, bright, high-tech and furnished with high-end appliances and thoughtful detail, such as a Keurig cubby upstairs and robes in the closets. The villa is just Steps from a beach to snorkel. Our master bedroom was huge with high ceilings. The master bedroom balcony was spacious and provided a view of the bay. We played many card games at night and sipped coffee in the morning. Snorkel equipment and beach chairs are provided to use....
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, (10)
"We had an amazing stay at Villa Belvedere. Although the check in process didn’t go as smooth as we’d like, the rest of the stay was perfect. We originally coordinated with the property manager to meet us at the ferry dock but he did not show up or answer our calls which was very concerning. We eventually got in touch with him after picking up our Jeep rental and driving to the grocery store. Since it was about 3pm at this point the owner did remind us that check in was at 4pm so technically we...
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
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.

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Estate Chocolate Hole and Great Cruz Bay vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation 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 vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Estate Chocolate Hole and Great Cruz Bay vacation rentals we have selected for you start as low as CA $176 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 vacation 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 vacation.

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 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 45 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?

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 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.

Recent reviews of Estate Chocolate Hole and Great Cruz Bay properties
Expedia verified reviews

BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay

BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay

5/5 Excellent
Beautiful Villa
"Fantastic location in Chocolate Hole. The Villa itself is clean, bright, high-tech and furnished with high-end appliances and thoughtful detail, such as a Keurig cubby upstairs and robes in the closets. The villa is just Steps from a beach to snorkel. Our master bedroom was huge with high ceilings. The master bedroom balcony was spacious and provided a view of the bay. We played many card games at night and sipped coffee in the morning. Snorkel equipment and beach chairs are provided to use. Construction on other villas is ongoing, but was not noisy. Very quiet at night. The entrance road is deceiving, but after the modest gravel road, the beautifully landscaped villas emerge."
A verified traveller stayed at BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
Posted 3 days ago
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay