Photo by Eric Sturgeon

Estate Trunk Bay Holiday Rentals

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Our top choices for Estate Trunk Bay holiday rentals

9.4 out of 10, Exceptional, (223)
"Clean, quiet, convenient location. Perfect stay!!!"
United States
Glenda
The price is AU$298
includes taxes & fees
30 Dec - 31 Dec
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

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 AU$1,156
includes taxes & fees
6 Jan - 7 Jan 2026
Villa Island Paradise

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 AU$317
includes taxes & fees
3 Jan - 4 Jan 2026
Flamboyan on the Bay Resort and Villas
9.6 out of 10, Exceptional, (179)
"This room was absolutely perfect for my stay in St Thomas. It had everything I needed and was convenient to all the places I had to visit during my stay. A short walk to the beach, plenty of very good on site restaurants, nice pools, incredible views every day. As far as the room the bed was comfortable. It had a nice big TV, small kitchen with big frig, blender and Pod Coffee maker. I liked that they even supplied snorkeling gear, coolers, beach chairs, sunscreen lotion, bug spray, aloe and...
United States
Paul
The price is AU$394
includes taxes & fees
15 Jan - 16 Jan 2026
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

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
9.6 out of 10, Exceptional, (64)
"Loved our stay, close to town and beaches, great view and quiet neighborhood."
United States
Barbara
The price is AU$430
includes taxes & fees
19 Jan - 20 Jan 2026
Cozy Island Studio-5 Mins to Cruz Bay & Beaches

Apartment in St. Thomas

Seahorse:1 Queen Bed
10.0 out of 10, Exceptional, (15)
"Good nice quiet place "
United States
Judge C.
The price is AU$314
includes taxes & fees
25 Jan - 26 Jan 2026
Seahorse:1 Queen Bed
10.0 out of 10, Exceptional, (24)
"The location is amazing, the space was clean, and the kitchen area, shower, and snorkeling/beach gear were much appreciated!"
United States
Ann
The price is AU$366
includes taxes & fees
28 Dec - 29 Dec
Lameshur Bay Glamping Site with AC

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 AU$1,707
includes taxes & fees
4 Jan - 5 Jan 2026
Marriott's Frenchman's Cove
9.4 out of 10, Exceptional, (13)
"Beautiful views"
United States
Mark
Ocean View Sapphire Condo-Balcony & King Bed

Apartment in St Thomas

Paradise near Limetree Beach
9.6 out of 10, Exceptional, (13)
"This stay was very nice, the view was amazing,"
United States
Brandon r.
The price is AU$384
includes taxes & fees
8 Jan - 9 Jan 2026
Paradise near Limetree Beach
9.6 out of 10, Exceptional, (25)
"We only stayed one night before transferring to STJ. The unit is clean and quiet. We appreciated the convenient location near RedHook and Secret Harbor (Dinner/morning snorkel). I would recommend this rental."
United States
Kevin S.
The price is AU$992
includes taxes & fees
7 Jan - 8 Jan 2026
Luxury condo. Beach, pool, gym, yacht club! Back up generator!

Apartment in St Thomas

Eagles Nest Near the Beach
9.8 out of 10, Exceptional, (22)
"Great spot, great host. Albert was super helpful "
United States
McRae W.
The price is AU$346
includes taxes & fees
6 Jan - 7 Jan 2026
Eagles Nest Near the Beach
9.6 out of 10, Exceptional, (208)
"Great location and amazing views."
United States
Jewel W.
The price is AU$474
includes taxes & fees
30 Dec - 31 Dec
The Captain and the Mermaid - Adventures in Paradise are waiting!
10.0 out of 10, Exceptional, (30)
"Overall great property only semi complaint which is more needy than anything is the tent will get a bit stuffy and hot when the fans die. "
United States
Will C.
The price is AU$406
includes taxes & fees
31 Dec - 1 Jan 2026
Family Glamping Site with AC
9.0 out of 10, Wonderful, (32)
"Me and my gf’s loved staying here! Best part was having close beach access! "
United States
Maria
The price is AU$476
includes taxes & fees
26 Jan - 27 Jan 2026
Sophisticated Beach Condo-Ocean View-Sapphire
9.4 out of 10, Exceptional, (8)
"Very clean, great location, loved it all. "
United States
Sarah K.
The price is AU$506
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious 1bedroom with pool, garden views, and AC -1 mile from Cruz Bay
4.0 star property
8.6 out of 10, Excellent, (95)
"Amazing property and helpful staff. "
United States
Joseph
The price is AU$1,614
includes taxes & fees
25 Jan - 26 Jan 2026
Suite St. John at Gallows Point Resort
The price is AU$359
includes taxes & fees
31 Dec - 1 Jan 2026
Salt Pond Bay Glamping Site With AC
9.6 out of 10, Exceptional, (94)
"Relaxing time, beautiful views!"
United States
Andy W.
The price is AU$686
includes taxes & fees
12 Jan - 13 Jan 2026
Amazing villa steps from the pool with incredible views & FREE WiFi
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

Find out more about Estate Trunk Bay

Everything you need to know about Estate Trunk 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 Trunk Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Trunk Bay holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Estate Trunk Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Estate Trunk 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Estate Trunk 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 Trunk Bay holiday rentals we have selected for you start as low as AU$317 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Estate Trunk Bay rentals

At Expedia, we put the best Estate Trunk 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 Trunk 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 Trunk 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 Trunk 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 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 are some of the best holiday rentals that Estate Trunk Bay has to offer?

Beautiful views, walk to Secret Harbour Beach: This holiday home rental outside of Estate Trunk Bay is located by the ocean, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.