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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Estate Trunk Bay holiday rentals

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

1. 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 AU$675
includes taxes & fees
29 Sept - 30 Sept
Villa Island Paradise
A beach with turquoise water, sandy shore, and distant mountains.

2. 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$259
includes taxes & fees
29 Sept - 30 Sept
Flamingo Grove Glamping Site with AC
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

3. 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, (254 reviews)
"Enjoyed our stay "
United States
Jason A.
The price is AU$283
includes taxes & fees
29 Sept - 30 Sept
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
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 AU$562
includes taxes & fees
11 Oct - 12 Oct
The Westin St. John Resort Villas
A beach with clear turquoise water, a sandy shore, and a distant island with buildings.

5. 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, (202 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$283
includes taxes & fees
29 Sept - 30 Sept
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

6. 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, (243 reviews)
"Stayed for two and had a great time. Location was close to many tourist spots, hiking, shopping, and entertainments."
United States
Dede C.
The price is AU$345
includes taxes & fees
29 Sept - 30 Sept
The Captain and the Mermaid - Adventures in Paradise are waiting!
A clear turquoise sea with people swimming.

7. 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$403
includes taxes & fees
29 Sept - 30 Sept
Breathtaking Views from Sapphire Village II
An outdoor seating area with a pool view, covered by white canopies, and surrounded by potted plants.

8. Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (45 reviews)
"Clean room, AC worked great, pool is very close. Overall, a really cool place to stay."
United States
Michael
The price is AU$402
includes taxes & fees
29 Sept - 30 Sept
Sophisticated Beach Condo-Ocean View-Sapphire
A restaurant with outdoor seating, palm trees, and a mountain in the background.

9. Octopus Den Glamping Site with AC

Octopus Den Glamping Site with AC
St John
10.0 out of 10, Exceptional, (8 reviews)
"Great for a short stay!"
United States
Kimberly J.
The price is AU$261
includes taxes & fees
30 Sept - 1 Oct
Octopus Den Glamping Site with AC
A room with a TV, wicker furniture, and a view of the ocean.

10. 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$1,046
includes taxes & fees
1 Oct - 2 Oct
Suite St. John at Gallows Point Resort
A beach with turquoise water, sandy shore, and distant mountains.

11. 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$538
includes taxes & fees
10 Oct - 11 Oct
Lameshur Cottage's Guest House
A balcony with a table, chairs, and a view of a turquoise sea and green hills.

12. 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 AU$1,241
includes taxes & fees
29 Sept - 30 Sept
Peter Bay Gatehouse
A beach with clear turquoise water, sandy shore, and buildings in the background.

13. 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)
"Great place. I stay here two times a year. Always consistent. Always clean."
United States
John H.
The price is AU$331
includes taxes & fees
29 Sept - 30 Sept
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

14. 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, (174 reviews)
"Excellent location and very nice place to visit and Sudi's Bar/restaurant is the place to be and the whole staff is Excellent and the food is delicious and reminds you of Cheers 😎."
United States
Quincy
The price is AU$336
includes taxes & fees
30 Sept - 1 Oct
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
A beach with clear turquoise water and waves.

15. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (164 reviews)
"Host was very courteous!! I will definitely be back!!"
United States
Tyneisha
The price is AU$369
includes taxes & fees
29 Sept - 30 Sept
The Mermaid's Pearl at Sapphire Beach
A balcony with a round table and chairs, a potted plant, and a view of a sunset over a body of water.

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

Sunset Hideaway Suite - Oceanview/central to Cruz Bay
St John
9.8 out of 10, Exceptional, (20 reviews)
"Clean and spacious! Great location, proximity to Cruz Bay!"
United States
Laina M.
The price is AU$581
includes taxes & fees
30 Sept - 1 Oct
Sunset Hideaway Suite - Oceanview/central to Cruz Bay
A covered outdoor area with a table and chairs, a view of the sea, and potted plants.

17. St. John Escape 4-304

St. John Escape 4-304
St. John
10.0 out of 10, Exceptional, (130 reviews)
"We had a wonderful time staying in this beautiful property while visiting St John! "
United States
Kari H.
The price is AU$1,058
includes taxes & fees
8 Oct - 9 Oct
St. John Escape 4-304
A beach with clear turquoise water, sandy shore, and buildings in the background.

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

Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
St. Thomas
9.8 out of 10, Exceptional, (142 reviews)
"We had an amazing stay, the condo was very clean and close to several beaches and restaurants."
United States
Jessica D.
The price is AU$425
includes taxes & fees
29 Sept - 30 Sept
Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
A beach with turquoise water, sandy shore, and distant mountains.

19. Turtle Nest Family Glamping Site with AC

Turtle Nest Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful property and a fun experience! Would stay again."
United States
Carlee D.
The price is AU$408
includes taxes & fees
29 Sept - 30 Sept
Turtle Nest Family Glamping Site with AC
A room with a hammock chair, a colorful door, and a wall-mounted sculpture.

20. St John Inn Boutique Hotel Suite w/ Kitchenette

St John Inn Boutique Hotel Suite w/ Kitchenette
Cruz Bay
9.8 out of 10, Exceptional, (7 reviews)
"Fantastic we'll go again! "
United States
Paul D.
The price is AU$483
includes taxes & fees
3 Oct - 4 Oct
St John Inn Boutique Hotel Suite w/ Kitchenette
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

Bluebeard's Castle Resort

Bluebeard's Castle Resort

10/10 Excellent
"Staff and everything was awesome, will definitely be back ."
Johnise 3-night trip
Posted 2 hours ago
Bluebeard's Castle Resort

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$325 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?

Mampoo Hill-- a Beachfront House 60 feet from the Ocean with optional Jeep: This holiday home rental outside of Estate Trunk Bay is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 hot tub.

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.