Estate Trunk Bay Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Estate Trunk Bay holiday rentals

Exterior
Villa Island Paradise

Villa in St. John

Villa Island Paradise
4.0 star property
9.2 out of 10, Wonderful, (7)
"Very safe and secure place! Also very clean! Just uphill from cruz bay "
United States
Tyler
The price is S$992
includes taxes & fees
6 Jan - 7 Jan, 2026
Villa Island Paradise
Exterior
Flamboyan on the Bay Resort and Villas

Condo resort in St. Thomas

Flamboyan on the Bay Resort and Villas
3.5 star property
8.6 out of 10, Excellent, (807)
"location nice pool "
United States
Gary
The price is S$302
includes taxes & fees
19 Jan - 20 Jan, 2026
Flamboyan on the Bay Resort and Villas
Aerial view
Beachfront Villas at Crystal Cove

Apartment in St. Thomas

Beachfront Villas at Crystal Cove
4.0 star property
9.6 out of 10, Exceptional, (150)
"Second time there. Just an over all beautiful property. "
United States
Erik
Beachfront Villas at Crystal Cove
Exterior
Marriott's Frenchman's Cove

Condo resort in St. Thomas

Marriott's Frenchman's Cove
4.0 star property
9.0 out of 10, Wonderful, (189)
"the view was amazing… the room was perfect and very clean! Highly recommend! "
United States
Ron
The price is S$1,472
includes taxes & fees
4 Jan - 5 Jan, 2026
Marriott's Frenchman's Cove
View from property
Suite St. John at Gallows Point Resort

Aparthotel in St. John

Suite St. John at Gallows Point Resort
4.0 star property
8.6 out of 10, Excellent, (95)
"Amazing property and helpful staff. "
United States
Joseph
The price is S$1,392
includes taxes & fees
11 Jan - 12 Jan, 2026
Suite St. John at Gallows Point 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

Windward Passage Hotel

Windward Passage Hotel

10/10 Excellent
"Customer service "
LaVern 5-night trip
Posted 3 days ago
Windward Passage Hotel

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 Gibney 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.