Estate Chocolate Hole and Great Cruz Bay Holiday Rentals from AU$143: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Estate Chocolate Hole and Great Cruz Bay has to offer?

The Cottage at Villa Indigo : This holiday home rental outside Estate Chocolate Hole and Great Cruz Bay is located in the mountains, and offers a private garden, Netflix and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Our travellers also rate Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise! as a favourite home for rent in Estate Chocolate Hole and Great Cruz Bay.

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In two weeks

In two months

In three months

In four months

Our top choices for Estate Chocolate Hole and Great Cruz Bay holiday rentals

Outdoor pool, pool cabanas (surcharge), pool loungers

The Westin St. John Resort Villas

St. John

Laura

includes taxes & fees

2 June - 3 June

Beach nearby, sun-loungers, beach towels

Lameshur Bay Glamping Site with AC

St John

John

includes taxes & fees

10 May - 11 May

Family Glamping Site with AC

St John

Kelly

includes taxes & fees

10 May - 11 May

Salt Pond Bay Glamping Site With AC

St John

Jim H.

includes taxes & fees

10 May - 11 May

Lameshur Cottage's Guest House

St John

Suresh Kumar B.

includes taxes & fees

6 June - 7 June

Flamboyan on the Bay Resort and Villas

St. Thomas

Kim

includes taxes & fees

24 May - 25 May

Villa Island Paradise

St. John

Sarah

includes taxes & fees

14 May - 15 May

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address

Maho Bay Quarter

Erik R.

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Top Estate Chocolate Hole and Great Cruz Bay Hotel Reviews

The Westin St. John Resort Villas

6/10 Okay

"My stay at this property was ultimately disappointing, especially considering the high price. While the grounds were well kept and clearly cared for, many other aspects of the experience fell short. Service The staff were consistently rather rude, which set a negative tone from the start. Interactions felt dismissive instead of welcoming. Food & Dining The food was mediocre at best, and the menu was extremely limited. Breakfast was only served 2 out of the 5 days that we were on property. This was frustrating and inconvenient. Facilities The pool clearly needed cleaning and updating. It didn’t feel inviting or well maintained a separate children’s area would be a great upgrade. Rooms & Property Condition The property itself shows its age. While the rooms have been somewhat updated, the overall feel is still dated and doesn’t match the price point. Value For what we received, the stay felt very expensive. The quality simply didn’t align with the cost. Positive Note The one standout was the well‑kept grounds, which were pleasant and nicely maintained. "

Poolside Paradise at Castaway Villa with new kitchen, baths, & Tesla batteries !

10/10 Excellent

"Beautiful property and exactly as described. We loved the pool and amazing views. The kitchen was well appointed and everything was very clean. We had 3 couples and there was plenty of space for everyone to enjoy being together. We would definitely love to stay there again!"

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!

10/10 Excellent

"We had everything we needed to cook any meal. The rooms were clean and comfortable. We really loved the outdoor showers! Parking was a non-issue. The pool and view were amazing! Honestly, the perfect space and location for two couples. "

Poi Pu St John - Great Views, Total Privacy & Tesla Solar Backup System

6/10 Okay

"The property was clean and had a great deck with amazing views. The location was great- far enough from the traffic in Cruz Bay, but close enough that it took less than 10 minutes to get to restaurants, the grocery store, etc. The kitchen was well appointed with everything we needed. Communication with the host was good and she was very responsive. However, communication with the property manager wasn’t great- the directions to get there were not accurate based on where we were coming from and it took several calls and us driving around and around to figure out where to go. The front door stuck badly and took multiple tries to open and close. There was only AC in the two bedrooms and loft got really hot, so our son had to move downstairs and share the other bedroom. The couch in the living room was stained and very uncomfortable. Also, be aware that there is only 1 shower for the whole house- we didn’t realize this as the listing showed 2 bathrooms. There were two shower heads in said shower, but only one of them would allow hot water to come out. And due to the fact that there is only AC in the bedrooms, the bathrooms were very stuffy and hot. Lack of central AC may be the case for most houses in St. John, but as this was our first time there, I can’t say for sure."

New rental, Newly Renovated 3br/2ba - open main room/beautiful view/large pool

4/10 Poor

"Great location, beautiful setting, very private and lots of space. So many things we loved. Many we did not. Oven did not work, ice maker did not work. Did have lots of little details most do not. Pool fills daily with leaves. Lots of work to use for a short time. We had to clean it twice daily. Large trees filled with large birds crapping all over the deck and seating areas. Lots! Lots of bugs that needed to be cleaned daily. Quick contact with mgr but he would never show. Blew us off several days. Never showed up. Doors did not lock but we felt safe. Overall we liked our time. "

Cute Cozy Cottage with private entrance and ocean views in prime neighborhood

10/10 Excellent

"Craig was available by phone and lived right next door. He brought over a larger umbrella for the porch when we were there.Loved sitting out there in the shade. Nice view and always a breeze!Quite a few steps to the cottage, but lit by solar lights. Never a power failure for us because of their solar!"

Samba Azul~ Convenient location and beautiful sunsets

10/10 Excellent

"We absolutely loved our stay at Sambal Azul! The house was even better than pictured. It was pristine, had beautiful views, comfortable furniture and a well stocked kitchen. We ate dinner on the porch every night while the kids swam. We used the grill most days, and the house was also stocked with coolers, pool noodles, beach chairs, sunscreen- anything we needed for the beach. It also got great breezes-we kept the windows open most of the time we were at the house and we were always comfortable out on the porch. Can’t wait to go back! "

Private cottage in great location with a Path to Chocolate Hole Beach

10/10 Excellent

"Loved it. Host was extremely responsive and offered terrific suggestions for things to do. House was cozy and the breeze that comes through is phenomenal. Loved that there were beach chairs, towels, and snorkel gear available. The washer and dryer came in handy. Loved the view. Would stay again. "

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$143 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?

The Cottage at Villa Indigo: This holiday home rental outside Estate Chocolate Hole and Great Cruz Bay is located in the mountains, and offers a private garden, Netflix and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Our travellers also rate Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise! as a favourite home for rent in Estate Chocolate Hole and Great Cruz Bay.

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

Choose from 47 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. Trunk Bay and Sapphire Beach are other popular places to visit in the area.

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.

Estate Chocolate Hole and Great Cruz Bay Holiday Rentals

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Check prices for these dates

Our top choices for Estate Chocolate Hole and Great Cruz Bay holiday rentals

The Westin St. John Resort Villas

Lameshur Bay Glamping Site with AC

Family Glamping Site with AC

Salt Pond Bay Glamping Site With AC

Lameshur Cottage's Guest House

Flamboyan on the Bay Resort and Villas

Villa Island Paradise

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!

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

Marriotts Frenchmans Cove - 2 Bedroom

Stunning St. Thomas Condo for Your Tropical Escape

Sapphire Beachfront, Step Right to the Beach, WIFI, Central AC, Great Views

Breathtaking Views from Sapphire Village

Peter Bay Gatehouse

Luxury Beachside Escape with Private Pool and Generator!

Sophisticated Beach Condo-Ocean View-Sapphire

JJ's-Spacious Home w/ Open Floor Plan & Pool !

The Mermaid's Pearl at Sapphire Beach

Find holiday rentals that suit your style

Top Estate Chocolate Hole and Great Cruz Bay Hotel Reviews

The Westin St. John Resort Villas

Find out more about Estate Chocolate Hole and Great Cruz Bay

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