Estate Chocolate Hole and Great Cruz Bay Holiday Rentals from €203: Search Short-Term Rentals

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

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

1. The Westin St. John Resort Villas

St. John

Treacy

includes taxes & fees

1 Nov - 2 Nov

A room with a large window, a black metal console table, a white vase with dried plants, and a potted plant on the left.

2. LAGUNA SUN Caribbean Hideaway your St. John Escape New aibnb

St john

includes taxes & fees

17 Nov - 18 Nov

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

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

Cruz Bay

Jeremy F.

includes taxes & fees

25 Oct - 26 Oct

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

4. Villa Island Paradise

St. John

Zach Ezekiel Azurus

includes taxes & fees

18 Oct - 19 Oct

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

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

St. Thomas

Camierre

includes taxes & fees

23 Oct - 24 Oct

A neatly made bed with a grey comforter and pillows, a ceiling fan, a wall-mounted lamp, and a beach-themed painting above the bed.

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

St. Thomas

Candice D.

includes taxes & fees

18 Oct - 19 Oct

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

St Thomas

angela C.

includes taxes & fees

20 Oct - 21 Oct

A beach with clear turquoise water and waves.

8. The Mermaid's Pearl at Sapphire Beach

St. Thomas

Tyneisha

includes taxes & fees

18 Oct - 19 Oct

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Top Estate Chocolate Hole and Great Cruz Bay Hotel Reviews

The Westin St. John Resort Villas

10/10 Excellent

"Everything was amazing! It will always be my go to when I come to visit."

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."

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!"

Sunset Beach: Beachfront Villa! Pool! Hot Tub!

10/10 Excellent

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Four adults, three kids. House was perfect. Pool was shaded in the afternoon so the kids could swim without concerns of getting burned. Kitchen very well equipped. No AC in main area not an issue, we were there in mid June as doors and windows on all four sides. Great covered porch on upper level perfect for coffee in the morning and relaxing anytime. They provide beach towels, huge packing help. And washing machine and dryer allowed us to wash bathing suits mid trip. Not far from grocery store. Would return every year if the kids would come"

Spacious 2/Bed, 2/Ba, Pool, A/C Bedrooms, Screened Porch, Wi-Fi

8/10 Good

"Property is exactly as described, property manager was awesome. Property was clean and had a great ocean view. The only compliant I would have, is the king sized bed mattress. The king mattress is extremely soft and has sagged so much that the center sinks into a V‑shape. No matter where you lie, you end up sliding toward the middle. It offers almost no back support, and you feel stuck in a dip, which makes it surprisingly hard to get out of bed. Other than the mattress I thought the property was great."

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, apart-hotels, 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 favorite 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 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 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 €203 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 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?

Private Pool overlooking ocean, large deck on Estate Property. Great Privacy.: This highly rated holiday home rental in Estate Chocolate Hole and Great Cruz Bay is located by the ocean, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games. Some other homes for rent in Estate Chocolate Hole and Great Cruz Bay include Secluded Oceanfront Villa • Pool • Incredible Views • In-House Car Rental and Poi Pu St John - Great Views, Total Privacy & Tesla Solar Backup System.

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

Choose from 54 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 Rendezvous Bay 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.

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Check prices for these dates

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

1. The Westin St. John Resort Villas

2. LAGUNA SUN Caribbean Hideaway your St. John Escape New aibnb

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

4. Villa Island Paradise

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

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

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

8. The Mermaid's Pearl at Sapphire Beach

9. Breathtaking Views from Sapphire Village II

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

11. Flamingo Grove Glamping Site with AC

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

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

14. Updated: Luxe Condo steps from Sapphire Beach!

15. Bluebeard's Castle Resort

16. 1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level

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

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

19. Suite St. John at Gallows Point Resort

20. Octopus Den Glamping Site with AC

Find holiday rentals that suit your style

Top Estate Chocolate Hole and Great Cruz Bay Hotel Reviews

The Westin St. John Resort Villas

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

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

Secluded Oceanfront Villa • Pool • Incredible Views • In-House Car Rental

Villa Chez Shell has recently installed Tesla Battery!

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

Pet friendly. Kayak, paddle board, snorkel, or hike to the beach.

Sunset Beach: Beachfront Villa! Pool! Hot Tub!

Spacious 2/Bed, 2/Ba, Pool, A/C Bedrooms, Screened Porch, Wi-Fi

Find out more about Estate Chocolate Hole and Great Cruz Bay

Frequently asked questions

Go further with the Expedia app

Holiday Rentals in Estate Chocolate Hole and Great Cruz Bay

Change your mind

Treat yourself

Be picky

Check prices for these dates

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

1. The Westin St. John Resort Villas

2. LAGUNA SUN Caribbean Hideaway your St. John Escape New aibnb

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

4. Villa Island Paradise

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

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

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

8. The Mermaid's Pearl at Sapphire Beach

9. Breathtaking Views from Sapphire Village II

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

11. Flamingo Grove Glamping Site with AC

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

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

14. Updated: Luxe Condo steps from Sapphire Beach!

15. Bluebeard's Castle Resort

16. 1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level

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

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

19. Suite St. John at Gallows Point Resort

20. Octopus Den Glamping Site with AC

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

Frequently asked questions

Go further with the Expedia app