Estate Chocolate Hole and Great Cruz Bay Vacation Rentals from ￥35,922: Search Short-Term Rentals

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

A resort with a central pool, palm trees, and a view of the ocean.

1. The Westin St. John Resort Villas

St. John

"Unfortunately, the pool was under construction during our stay and unusable, but we didn't allow that to stop us. The beach was quite and relaxing, thus Westin has a family vibe and good for children. The staff was friendly. I do think they can do better at advertising the water and children's activities. The rooms were excellent and resturants too. Ferry service and crew were great too. Great stay for a family of 5!"

Shani

￥62,118 total

includes taxes & fees

Oct 8 - Oct 9

A beach with clear turquoise water, white sand, and rocky outcrops.

2. Luxury Villa w/ Private Pool, Game Room, Outdoor Kitchen, Panoramic Ocean Views

Cruz Bay

Jeremy F.

￥329,460 total

includes taxes & fees

Sep 25 - Sep 26

A beach with turquoise water, sandy shore, and distant mountains.

3. Flamingo Grove Glamping Site with AC

St John

John

￥28,668 total

includes taxes & fees

Sep 24 - Sep 25

A restaurant with outdoor seating, palm trees, and a mountain in the background.

4. Octopus Den Glamping Site with AC

St John

Kimberly J.

￥28,668 total

includes taxes & fees

Sep 30 - Oct 1

5. Turtle Nest Family Glamping Site with AC

St John

Carlee D.

￥45,286 total

includes taxes & fees

Sep 24 - Sep 25

A coastal landscape with a beach, clear blue waters, and lush greenery.

6. Villa Island Paradise

St. John

Zach Ezekiel Azurus

￥78,738 total

includes taxes & fees

Oct 11 - Oct 12

A wooden chair and table set against a lush green backdrop with a view of a valley and distant buildings.

7. Quiet cozy studio 5 minute drive from Cruz Bay

St John

Ashley

A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

8. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

St. Thomas

Jason A.

￥31,069 total

includes taxes & fees

Sep 26 - Sep 27

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

St Thomas

Quincy

￥39,484 total

includes taxes & fees

Sep 26 - Sep 27

A room with a TV, wicker furniture, and a view of the ocean.

10. Suite St. John at Gallows Point Resort

St. John

Sean

￥115,578 total

includes taxes & fees

Oct 1 - Oct 2

A beach with clear turquoise water, a sandy shore, and a distant island with buildings.

11. Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

St. Thomas

Alessandra C.

￥31,096 total

includes taxes & fees

Sep 25 - Sep 26

A clear turquoise sea with people swimming.

12. Breathtaking Views from Sapphire Village II

St Thomas

Jason

￥44,972 total

includes taxes & fees

Sep 24 - Sep 25

13. The Captain and the Mermaid - Adventures in Paradise are waiting!

St Thomas

Dede C.

￥37,848 total

includes taxes & fees

Sep 25 - Sep 26

14. Lameshur Cottage's Guest House

St John

Shawn C.

￥58,343 total

includes taxes & fees

Oct 10 - Oct 11

A beach with clear turquoise water, sandy shore, and buildings in the background.

15. Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

St. Thomas

Jessica D.

￥47,450 total

includes taxes & fees

Sep 24 - Sep 25

16. Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

St Thomas

John H.

￥37,814 total

includes taxes & fees

Oct 10 - Oct 11

A balcony with a round table and chairs, a potted plant, and a view of a sunset over a body of water.

17. Sunset Hideaway Suite - Oceanview/central to Cruz Bay

St John

Laina M.

￥65,500 total

includes taxes & fees

Sep 24 - Sep 25

A covered outdoor area with a table and chairs, a view of the sea, and potted plants.

18. St. John Escape 4-304

St. John

Kari H.

￥119,536 total

includes taxes & fees

Sep 24 - Sep 25

A balcony with wicker chairs and a small table, overlooking a turquoise sea with boats and a hilly landscape.

19. Aahana Studio 4-303S

Cruz Bay, St. John

Charlene Z.

￥91,938 total

includes taxes & fees

Sep 24 - Sep 25

A beach with palm trees, clear blue sky, and a calm sea.

20. Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312

St Thomas

Steph M.

￥36,949 total

includes taxes & fees

Oct 19 - Oct 20

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Top Estate Chocolate Hole and Great Cruz Bay Hotel Reviews

4 bedroom, 4 bathroom. Private Pool, Ocean views. Chocolate Hole, Cruz Bay.

10/10 Excellent

"Everything was great.The only request is to please provide a backup generator. We lost power for 16 hrs and no backup generator. With 10People 2 being babies 1,3 and 2 being 73 and 72. It was a pretty rough go with no running water, no toilets and no a/c. Other thank that the management ladies are amazing and Ricki the cab driver was definitely the highlights. ThankYou for an amazing week."

The Westin St. John Resort Villas

10/10 Excellent

"Unfortunately, the pool was under construction during our stay and unusable, but we didn't allow that to stop us. The beach was quite and relaxing, thus Westin has a family vibe and good for children. The staff was friendly. I do think they can do better at advertising the water and children's activities. The rooms were excellent and resturants too. Ferry service and crew were great too. Great stay for a family of 5!"

Villa Chez Shell has recently installed Tesla Battery!

10/10 Excellent

"We had a wonderful stay! The location was amazing—close to everything we wanted to explore—and the views were absolutely breathtaking. The pool was another highlight, especially with the incredible views from the pool area. It was such a beautiful place to come back to after a day of exploring the beaches.One thing we missed in the fine print before booking is that the main living area does not have air conditioning. We visited in August, during the hottest time of year, and the living space could get almost unbearably warm during the afternoon and evening. Thankfully, the bedrooms do have AC and were always cool and extremely comfortable, and the mornings in the main living area were very pleasant.For us, the lack of AC in the living area wasn’t a major issue since we spent most of our days out exploring and enjoying the beaches. It is just something to keep in mind if you’re traveling with anyone who may need to stay at the property during the day.Overall, the incredible location, beautiful pool, and absolutely breathtaking views made this a memorable stay. We’re very glad we got to experience it!"

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

10/10 Excellent

"We had a fantastic stay at Blue Dolphin! The hosts were excellent with communication from the start and provided great recommendations, including help with car rentals. Dwight, the property manager, was wonderful—he met us at the ferry and personally escorted us to the house to make sure we got settled and everything was in order.The outdoor area, pool, and incredible views were definite highlights. You never quite know if a vacation rental will live up to the photos and description, but Blue Dolphin exceeded our expectations. We would absolutely recommend it to anyone visiting St. John!"

Villa Colada, a 4-Bedroom St. John Villa Above Rendezvous Bay

10/10 Excellent

"A wonderful family getaway.Easy to get to. Check in was a breeze. We had 7 guests and we fit fine. Beautiful villa, clean with a great kitchen. Many games to choose from for inside and next to pool. Great views all around. Definitely a great option for a good size family getaway."

Villa Capiz: Luxury Hilltop Villa with Pool, Jacuzzi and Panoramic Ocean Views

10/10 Excellent

"Our stay here was amazing! The house was beautiful and unique. It had tons of space and the kitchen was stocked. The decor was great and every detail of the house was perfect. There were yoga mats provided and so many perfect spots to roll out a mat and practice. We enjoyed the pool and the hottub. The view was absolutely incredible, it was the best and most memorable part of our trip."

Find out more about Estate Chocolate Hole and Great Cruz Bay

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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 • Pool • Incredible Views • In-House Car Rental: 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. Some other homes for rent in Estate Chocolate Hole and Great Cruz Bay include Private Pool overlooking ocean, large deck on Estate Property. Great Privacy. and Poi Pu St John - Great Views, Total Privacy & Tesla Solar Backup System.

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

Choose from 54 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 Rendezvous Bay 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.

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Check prices for these dates

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

1. The Westin St. John Resort Villas

2. Luxury Villa w/ Private Pool, Game Room, Outdoor Kitchen, Panoramic Ocean Views

3. Flamingo Grove Glamping Site with AC

4. Octopus Den Glamping Site with AC

5. Turtle Nest Family Glamping Site with AC

6. Villa Island Paradise

7. Quiet cozy studio 5 minute drive from Cruz Bay

8. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

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

10. Suite St. John at Gallows Point Resort

11. Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

12. Breathtaking Views from Sapphire Village II

13. The Captain and the Mermaid - Adventures in Paradise are waiting!

14. Lameshur Cottage's Guest House

15. Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

16. Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

17. Sunset Hideaway Suite - Oceanview/central to Cruz Bay

18. St. John Escape 4-304

19. Aahana Studio 4-303S

20. Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312

Find vacation rentals that suit your style

Top Estate Chocolate Hole and Great Cruz Bay Hotel Reviews

4 bedroom, 4 bathroom. Private Pool, Ocean views. Chocolate Hole, Cruz Bay.

Stunning Views, Peaceful Location, Large Pool & Minutes from Cruz Bay

The Westin St. John Resort Villas

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

Villa Catalina, great views, private pool, full generator, AC, Last minute deals

Villa Chez Shell has recently installed Tesla Battery!

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

Villa Colada, a 4-Bedroom St. John Villa Above Rendezvous Bay

Villa Capiz: Luxury Hilltop Villa with Pool, Jacuzzi and Panoramic Ocean Views

Find out more about Estate Chocolate Hole and Great Cruz Bay

Frequently asked questions

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