Name: Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
Rating: 9.4

Your Estate Chocolate Hole and Great Cruz Bay Vacation

Say bye-bye to the stress of planning and hello to a Estate Chocolate Hole and Great Cruz Bay vacation package. With your travel details organized before you take off, you can focus on discovering the best of this city, starting with Belle Vue, which is great for views, underwater activities and watersports. If your trip to Estate Chocolate Hole and Great Cruz Bay includes some sightseeing, check out renowned attractions like Trunk Bay, Annaberg Plantation and Cinnamon Bay Beach. No matter your travel plans or budget, organizing a tailored Estate Chocolate Hole and Great Cruz Bay vacation is a breeze with Expedia.

Top Estate Chocolate Hole and Great Cruz Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Sapphire Sanctuary by the Sea

CA $2,155

per person

Aug 1 - Aug 8

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to St. Thomas (STT)

9.2/10 Wonderful! (47 reviews)

This place was close to all the amenities and was a comfortable beach side bungalow for grampa to entertain his grandsons and his kids. Cool place. A kitchen to take care of family needs and a step away from beachside bar. The unit itself great for 5 and has 2 nice bathrooms. We had access to snorkeling equipment, beach towels, beach chairs and a great sandy beach.

Reviewed on Nov 23, 2025

Margaritaville Vacation Club - St. Thomas

CA $2,652

per person

Aug 1 - Aug 8

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to St. Thomas (STT)

8/10 Very Good! (2,475 reviews)

The property was beautiful, the staff was helpful and friendly, and we really took advantage of the Margaritaville branded margarita maker in the room.

Reviewed on Jun 20, 2026

Limetree Beach Resort by Club Wyndham

CA $2,706

per person

Aug 1 - Aug 8

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to St. Thomas (STT)

8.2/10 Very Good! (222 reviews)

Surprised by power outages. TVS did not include guides to determine channels. The restaurant service seemed rather slow.

Reviewed on May 20, 2026

At Home in the Tropics

CA $2,236

per person

Aug 1 - Aug 8

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to St. Thomas (STT)

9.8/10 Exceptional! (177 reviews)

My wife and I stayed here for our honeymoon. At first we were a little taken back by the size of the space but once we stepped out on the balcony we fell in love with it! Mark was incredibly nice and helpful with recommendations and attending to our needs! Parking was a little tight with construction going on in the surrounding area but honestly parking was tight throughout the entire island. We took advantage of the location and visited the shoppes frequently! The views were beautiful and the space was exactly what we needed! When we come bact to St Thomas we will stay here again for sure!

Reviewed on Jun 16, 2026

Club Wyndham Elysian Beach Resort

CA $2,180

per person

Aug 13 - Aug 19

found 10 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to St. Thomas (STT)

8/10 Very Good! (186 reviews)

The property was very clean. The best part was the extremely friendly and helpful staff. Amazing restaurants! Very disappointed there was no service to our room during our stay which is one of those vacation perks.

Reviewed on Jun 5, 2026

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Estate Chocolate Hole and Great Cruz Bay Hotel Deals

The Westin St. John Resort Villas

300B Chocolate Hole St. John

CA $1,032

CA $1,161 total

Jul 5 - Jul 6

includes taxes & fees

8.2/10 Very Good! (491 reviews)

"Beautiful hotel with amazing views and a great atmosphere. The property is well maintained and the staff was wonderful. My only concern was the large number of iguanas and the amount of iguana droppings around the grounds. Addressing this issue would make the experience much better. Overall, a lovely ..."

Reviewed on Jun 7, 2026

Blue Dolphin Villa Great Cruz Bay FEATURING A NEW MASTER BEDROOM gorgeous views

Cruz Bay St John

9.8/10 Exceptional! (83 reviews)

"Everything from, the host, to the property manager, to the actual house was amazing. Dwight was extremely helpful in cases where he didn't have to be. Highly recommend!"

Reviewed on Jun 5, 2026

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

St John

9.4/10 Exceptional! (36 reviews)

"Villa Belvidere was our week in paradise with incredible ocean views of St Thomas and surrounding islands, our own private pool, patio and gardens, grill and deck overlooking the ocean, and balconies off of each private bedroom. The outdoor shower made of natural stone and shells was such a treat ..."

Reviewed on Jun 2, 2026

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See all 527 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.