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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Estate Trunk Bay holiday rentals

Flamboyan on the Bay Resort and Villas

Flamboyan on the Bay Resort and Villas
3.5 star property
St. Thomas
8.6 out of 10, Excellent, (877 reviews)
"Excellent stay resort was perfectly located "
United States
andrew
The price is AU$143
includes taxes & fees
6 June - 7 June
Flamboyan on the Bay Resort and Villas

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, (486 reviews)
"Excellent place for families "
United States
Laura
The price is AU$1,133
includes taxes & fees
20 May - 21 May
The Westin St. John Resort Villas

St Thomas Cliffside Villa With Pool & Hot Tub!

St Thomas Cliffside Villa With Pool & Hot Tub!
3.5 star property
St. Thomas
The price is AU$1,692
includes taxes & fees
17 May - 18 May
St Thomas Cliffside Villa With Pool & Hot Tub!

Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (197 reviews)
"Everything was great. Check in area was a bit clunky with traffic and parking, but it was a weekend and lots of people. "
United States
Remmie
The price is AU$1,333
includes taxes & fees
14 May - 15 May
Marriott's Frenchman's Cove

Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.4 out of 10, Very good, (20 reviews)
"Staying at the gate house was wonderful. Walk to beach was a little longer than expected because of the sharp incline. Very nice place to stay!! "
United States
jonathan
The price is AU$1,448
includes taxes & fees
14 May - 15 May
Peter Bay Gatehouse

Beachfront Villas at Crystal Cove

Beachfront Villas at Crystal Cove
4.0 star property
St. Thomas
9.4 out of 10, Exceptional, (160 reviews)
"Beautiful accommodations friendly staff 😍 "
Canada
Valeri
The price is AU$1,183
includes taxes & fees
21 May - 22 May
Beachfront Villas at Crystal Cove

Shibui Cove

Shibui Cove
2.0 star property
St. Thomas
7.2 out of 10, Good, (5 reviews)
"I had a great stay here. The view was absolutely stunning. Being up on the side of the mountain was great. Very private but less than 5 min away from town. I will definitely stay again. "
United States
Adam R
The price is AU$396
includes taxes & fees
17 May - 18 May
Shibui Cove

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$1,155
includes taxes & fees
6 June - 7 June
Sunset Ridge Villas Unit D

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, (100 reviews)
"Beautiful property, with unbelievable views! Easy walk to town! Staff was friendly and helpful! Would absolutely stay here again! "
United States
Kristen
The price is AU$1,139
includes taxes & fees
14 May - 15 May
Suite St. John at Gallows Point Resort

The Landmark Apartment

The Landmark Apartment
2.5 star property
St. Thomas
9.0 out of 10, Wonderful, (17 reviews)
"Yes it was very clean and staff was very helpful"
United States
Fran
The price is AU$544
includes taxes & fees
15 May - 16 May
The Landmark Apartment

The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is AU$546
includes taxes & fees
15 May - 16 May
The Perch at Hawk Hill

Little Indigo Apartments

Little Indigo Apartments
3.5 star property
St. Thomas
8.0 out of 10, Very good, (28 reviews)
"Kitchen utensils were basic but got the job done! "
United States
Jackson
The price is AU$418
includes taxes & fees
14 May - 15 May
Little Indigo Apartments

Villa Indigo 1BR in Private Gated Estate

Villa Indigo 1BR in Private Gated Estate
3.5 star property
St. Thomas
8.8 out of 10, Excellent, (33 reviews)
"It was great, clean apartment and definitely recommend going again or booking in the future."
United States
John
The price is AU$470
includes taxes & fees
21 May - 22 May
Villa Indigo 1BR in Private Gated Estate

The Cottage at Villa Indigo

The Cottage at Villa Indigo
3.0 star property
St. Thomas
8.8 out of 10, Excellent, (15 reviews)
"We got a true dose of the life experience on the island staying here. The entire experience was MAGICAL!!!! Me and my family will most definitely staying again when we come back "
United States
Oronde
The price is AU$565
includes taxes & fees
14 May - 15 May
The Cottage at Villa Indigo

Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.0 out of 10, Wonderful, (30 reviews)
"It was absolutely wonderful "
United States
Sarah
The price is AU$827
includes taxes & fees
19 May - 20 May
Villa Island Paradise

Aqua

Aqua
3.0 star property
St. Thomas
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable and beautiful area"
United States
Paola
The price is AU$489
includes taxes & fees
2 June - 3 June
Aqua
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.
Save an average of 15% on thousands of hotels when you're signed in

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$143 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?

Gorgeous View, Beach Access, Swimming Pool, Kayaks, Quiet Privacy - the East End: This holiday home rental outside of Estate Trunk Bay is located in the mountains, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and a selection of games.

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.