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Estate Chocolate Hole and Great Cruz Bay Holiday Rentals

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Holiday Rentals in Estate Chocolate Hole and Great Cruz Bay

Smart TV
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
10.0 out of 10, Exceptional, (12)
"Great location, very clean and well equipped. Property was even better than we expected. Will stay here again when we return. David was very accessible and really great to deal with. Very comfortable beds and overall layout!!!"
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
Pool
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
9.6 out of 10, Exceptional, (9)
"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!
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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Aerial view
Hilltop Villas at Bluebeard's Castle by Capital Vacations
3.0 star property
8.6 out of 10, Excellent, (1164)
"Beautiful place to vacation 😍 "
Hilltop Villas at Bluebeard's Castle 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, (778)
"It was peace an quiet "
Castle Villas at Bluebeard's by Capital Vacations
On the beach, white sand, sun-loungers, beach umbrellas
Secret Harbour Beach Resort
4.0 star property
8.8 out of 10, Excellent, (1181)
"Very clean and updated unit."
The price is NZ$1,105
per night
3 Jun - 4 Jun
Secret Harbour Beach 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
Premium Studio | Terrace/patio
Flamboyan on the Bay Resort and Villas
3.5 star property
8.8 out of 10, Excellent, (417)
"We had a great stay at Flamboyan! They were very friendly and accommodating. Our rooms were comfortable and had wonderful views of Magen’s Bay. The steel pan entertainment by Andrew Douglas during dinner was wonderful. I would love to stay again."
The price is NZ$258
per night
1 Jun - 2 Jun
Flamboyan on the Bay Resort and Villas
Exterior
Pirates Pension at Bluebeard's Castle by Capital Vacations
3.0 star property
8.4 out of 10, Very good, (559)
"Beautiful view "
Pirates Pension at Bluebeard's Castle by Capital Vacations
On the beach, scuba diving, snorkelling, beach volleyball
Sapphire Beach Resort
3.0 star property
6.8 out of 10, (241)
"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
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 NZ$1,579
per night
27 May - 28 May
Marriott's Frenchman's Cove
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
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!
Aerial view
Sapphire Village Resort by Antilles Resorts
3.0 star property
6.2 out of 10, (288)
"Location is great!!! Pizza place and bar on the beach were really good. The room needed some serious update. Appliances, kitchen faucet rusted, patio light didn't work and a few lamp bulbs were out as well. The beach amd pool were awesome!!!!"
Sapphire Village Resort by Antilles Resorts
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
Condo, 1 Bedroom | 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
Outdoor pool
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 NZ$1,253
per night
9 Jun - 10 Jun
Suite St. John at Gallows Point Resort
Pool
Gorgeous Condo At Sapphire on St Thomas. Walk-in Level. Killer Island Views!
9.4 out of 10, Exceptional, (66)
"Killer views was an accurate description! Lovely sunrises and view from the gallery of the marina and the bay. Instructions beforehand with tips on what to bring, how to get to Sapphire Villages, and how to access the property were very helpful and made the trip easy. It would have been helpful though to have guest information in the unit as to the association requirements and amenities, such as where dumpsters are located, pool, beach, and dining options, as well as information on area...
Gorgeous Condo At Sapphire on St Thomas. Walk-in Level. Killer Island Views!
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!
Beach nearby, sun-loungers, beach towels
HEAVENLY VIEWS and PRIVATE POOL!!
10.0 out of 10, Exceptional, (137)
"Be still my heart! Arriving at Villa Celeste was exhilarating! Our stay at the Villa Vista for 7 days (6 nights) was heavenly. Our views of Coral Bay, Hurricane Hole, Hanson Bay, and the British Virgin Islands were phenomenally gorgeous and Lois gifted us with a keepsake to remember our view. The patio, our private pool, and the cozy villa are relaxing and beautiful. We loved the TLC we received from the house manager, Joy who checked in on us, stayed in touch, and we joined her for Thursday...
HEAVENLY VIEWS and PRIVATE POOL!!
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

Outdoor pool
The Westin St. John Resort Villas
4.5 star property
8.2 out of 10, Very good, (365)
"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 NZ$1,140
per night
11 Jun - 12 Jun
The Westin St. John Resort Villas
Smart TV
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
10.0 out of 10, Exceptional, (12)
"Great location, very clean and well equipped. Property was even better than we expected. Will stay here again when we return. David was very accessible and really great to deal with. Very comfortable beds and overall layout!!!"
BRAND NEW "Serenity" Beachfront Villa, steps away from Private Bay
Pool
Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
9.6 out of 10, Exceptional, (9)
"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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Estate Chocolate Hole and Great Cruz Bay holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Estate Chocolate Hole and Great Cruz Bay. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Estate Chocolate Hole and Great Cruz Bay. Seeing all the best attractions is bound to make you fall in love with Estate Chocolate Hole and Great Cruz Bay. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Estate Chocolate Hole and Great Cruz Bay short-term rentals, that won’t be hard to do.

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.

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

Choose from 43 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 Sunset Beach 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.

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

Modern Island Vibe

Modern Island Vibe

5/5 Excellent
Jen is the best
"Great property. Well located and stocked with absolutely everything you need"
A verified traveller stayed at Modern Island Vibe
Posted 3 days ago
Modern Island Vibe