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

Estate Trunk Bay Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Estate Trunk Bay holiday rentals

A balcony with a table, chairs, and a view of a turquoise sea and green hills.

1. Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.2 out of 10, Very good, (21 reviews)
"Outstanding view from the villa"
United States
Thomas
The price is S$1,116
includes taxes & fees
25 Sept - 26 Sept
Peter Bay Gatehouse
A coastal landscape with a beach, clear blue waters, and lush greenery.

2. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (41 reviews)
"View was amazing . Unit itself was very unique"
United States
Zach Ezekiel Azurus
The price is S$655
includes taxes & fees
11 Oct - 12 Oct
Villa Island Paradise
A room with a TV, wicker furniture, and a view of the ocean.

3. Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort
4.0 star property
St. John
8.8 out of 10, Excellent, (106 reviews)
"Friendly staff. Beautiful property."
United States
Sean
The price is S$940
includes taxes & fees
1 Oct - 2 Oct
Suite St. John at Gallows Point Resort
A resort with a central pool, palm trees, and a view of the ocean.

4. The Westin St. John Resort Villas

The Westin St. John Resort Villas
4.5 star property
St. John
8.4 out of 10, Very good, (507 reviews)
"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!"
United States
Shani
The price is S$505
includes taxes & fees
8 Oct - 9 Oct
The Westin St. John Resort Villas
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

5. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (856 reviews)
"Bluebeards is one of my favorite places to stay when I am on the island."
United States
Erica
The price is S$292
includes taxes & fees
24 Oct - 25 Oct
Bluebeard's Castle Resort
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.
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Top Estate Trunk Bay Hotel Reviews

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

10/10 Excellent
"I stayed for my birthday weekend and everything was lovely and everyone was very helpful. although my stay was short I enjoyed every bit of it."
Nigel 4-night trip
Posted 5 hours ago
The Westin St. Thomas Beach Resort & Spa

Frequently asked questions

Can I find holiday rentals in Estate Trunk Bay?

Yes, there are holiday rentals close to the most popular sights in Estate Trunk Bay, or you can select a more secluded option if you're looking for a relaxing stay.

What can I see and do in Estate Trunk Bay?

Get outdoors into nature at a spot like Trunk Bay, or visit other top attractions such as Sapphire Beach. Cinnamon Bay and Cinnamon Bay Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Estate Trunk Bay?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Estate Trunk Bay. Holiday rentals offer amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for small groups.