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

Estate Trunk Bay Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Estate Trunk Bay holiday rentals

Aerial view

1. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (36 reviews)
"Beautiful location with stunning views and a peaceful atmosphere. The room was clean and comfortable, and the staff was friendly and helpful throughout the stay. Great option for a relaxing getaway in St. John."
United States
Quoc Phong Eric
The price is AU$728
includes taxes & fees
14 Aug - 15 Aug
Villa Island Paradise
Outdoor pool, pool cabanas (surcharge), pool loungers

2. 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, (501 reviews)
"We had a good stay at the Westin in St. John. Service is slow in the resort other than that everything else was good."
United States
Rituparna
The price is AU$594
includes taxes & fees
1 Sept - 2 Sept
The Westin St. John Resort Villas
Outdoor dining

3. Cozy Island Studio-5 Mins to Cruz Bay & Beaches

Cozy Island Studio-5 Mins to Cruz Bay & Beaches
St John
9.6 out of 10, Exceptional, (82 reviews)
"Amazing host and great property!"
United States
Stephanie K.
The price is AU$332
includes taxes & fees
15 Aug - 16 Aug
Cozy Island Studio-5 Mins to Cruz Bay & Beaches
Beach nearby

4. Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (141 reviews)
"Amazing place! Great host!!Close to Salt Pond."
United States
Shawn C.
The price is AU$501
includes taxes & fees
14 Aug - 15 Aug
Lameshur Cottage's Guest House
Beach

5. Flamingo House • PALM • Sunset view • Walk to town

Flamingo House • PALM • Sunset view • Walk to town
Cruz Bay
9.8 out of 10, Exceptional, (26 reviews)
"Great view from balcony. Cooler, beach chairs and towels provided"
United States
Inga W.
The price is AU$346
includes taxes & fees
14 Aug - 15 Aug
Flamingo House • PALM • Sunset view • Walk to town
Exterior

6. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (733 reviews)
"The view, the accommodation, the staff were all superb. I always stay there when I visit the Island."
United States
Janice
The price is AU$352
includes taxes & fees
12 Sept - 13 Sept
Bluebeard's Castle Resort
On the beach, sun-loungers, beach towels

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

Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
St. Thomas
9.6 out of 10, Exceptional, (175 reviews)
"Good location. "
United States
Anonymous traveller
The price is AU$387
includes taxes & fees
14 Aug - 15 Aug
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
Luxury Suite Ocean View Upper 15D | View from room

8. 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 AU$1,036
includes taxes & fees
14 Aug - 15 Aug
Suite St. John at Gallows Point Resort
Children’s activities

9. Sunset Ridge Villas Unit D

Sunset Ridge Villas Unit D
3.5 star property
St. John
9.4 out of 10, Exceptional, (3 reviews)
"This property was excellent especially for us a family of 4 with teenage kids. The space was great and the location was easy enough to get to. The amenities were excellent, from a fully outfitted kitchen to great beach resources such as chairs, cooler & snorkel equipment. "
United States
Jessica
The price is AU$902
includes taxes & fees
5 Sept - 6 Sept
Sunset Ridge Villas Unit D
Beach nearby, sun-loungers, beach towels

10. Flamingo Grove Glamping Site with AC

Flamingo Grove Glamping Site with AC
St John
9.8 out of 10, Exceptional, (30 reviews)
"Really enjoyed our stay. We felt well taken care of and loved the location!"
United States
John
The price is AU$258
includes taxes & fees
16 Aug - 17 Aug
Flamingo Grove Glamping Site with AC
On the beach, sun-loungers, beach towels

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

Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
St. Thomas
9.4 out of 10, Exceptional, (251 reviews)
"Enjoyed our stay "
United States
Jason A.
The price is AU$406
includes taxes & fees
11 Sept - 12 Sept
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
Outdoor dining

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

Sunset Hideaway Suite - Oceanview/central to Cruz Bay
St John
9.8 out of 10, Exceptional, (18 reviews)
"Clean and spacious! Great location, proximity to Cruz Bay!"
United States
Laina M.
The price is AU$571
includes taxes & fees
15 Aug - 16 Aug
Sunset Hideaway Suite - Oceanview/central to Cruz Bay
On the beach, sun-loungers, beach towels

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

The Captain and the Mermaid - Adventures in Paradise are waiting!
St Thomas
9.8 out of 10, Exceptional, (236 reviews)
"Nice for what we needed pool close, we didnt rent a car so be advised condo is up a big hill , if going to beach you have to walk a ways, if you have mobility issue you may need a car , Suzi bar was great every one friendly. Michael the host is very responsive."
United States
Steve
The price is AU$373
includes taxes & fees
20 Aug - 21 Aug
The Captain and the Mermaid - Adventures in Paradise are waiting!
Property grounds

14. Aahana Studio 4-303S

Aahana Studio 4-303S
Cruz Bay, St. John
10.0 out of 10, Exceptional, (58 reviews)
"4th time staying here. Great experience as always!"
United States
Glenn L.
The price is AU$820
includes taxes & fees
15 Aug - 16 Aug
Aahana Studio 4-303S
Luxury Penthouse | Balcony view

15. Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.4 out of 10, Very good, (20 reviews)
"Outstanding view from the villa"
United States
Thomas
The price is AU$1,235
includes taxes & fees
14 Aug - 15 Aug
Peter Bay Gatehouse
Beach nearby

16. Turtle Nest Family Glamping Site with AC

Turtle Nest Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful property and a fun experience! Would stay again."
United States
Carlee D.
The price is AU$403
includes taxes & fees
16 Aug - 17 Aug
Turtle Nest Family Glamping Site with AC
On the beach, sun-loungers, beach towels

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

Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
St. Thomas
9.6 out of 10, Exceptional, (199 reviews)
"We LOVED our stay and would recommend it to anyone going to St. Thomas. The location was unbeatable, and the property was equipped with everything we needed and more!"
United States
Alessandra C.
The price is AU$294
includes taxes & fees
28 Aug - 29 Aug
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
On the beach, sun-loungers, beach towels

18. Breathtaking Views from Sapphire Village II

Breathtaking Views from Sapphire Village II
St Thomas
8.8 out of 10, Excellent, (40 reviews)
"The room was beautiful great View locations on point for everything you needed within the area the only downfall I would say was the hill if you're walking and if you have any type of handicap but other than that beautiful place to stay"
United States
Jason
The price is AU$400
includes taxes & fees
14 Aug - 15 Aug
Breathtaking Views from Sapphire Village II
Beach nearby, sun-loungers, beach towels

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

Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
St Thomas
9.8 out of 10, Exceptional, (128 reviews)
"Room was just what we needed. Easy to check in and out. Good location near Sapphire Beach and some restaurants. It is a good hill so walking back is tougher but manageable for me and my 12 year old. "
United States
Nicole C.
The price is AU$337
includes taxes & fees
22 Aug - 23 Aug
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
Beach nearby, sun-loungers, beach towels

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

Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
St Thomas
9.6 out of 10, Exceptional, (94 reviews)
"Great location! The beach chairs and cooler were a nice bonus. The resort has a nice pool -- small, but clean and with several chairs and a restroom/changing room. Would definitely stay here again. "
United States
Steph M.
The price is AU$333
includes taxes & fees
14 Aug - 15 Aug
Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Estate Trunk Bay Hotel Reviews

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

8/10 Good
"The property was great. The only problem was the beach was closed because of the large amount of seaweed which really smelled. But they had shuttles available to take you to other beaches. The staff was great and very helpful."
Jose Luis 4-night trip
Posted 6 hours ago
Margaritaville Vacation Club - St. Thomas

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$352 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?

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!: This holiday home rental outside of Estate Trunk Bay is located on the beach, and has a balcony, a private garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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 Virgin Islands National Park. Sapphire Beach and Cinnamon Bay 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.