Estate Trunk Bay Vacation 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
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Estate Trunk Bay vacation rentals

Beach nearby

Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (140 reviews)
"Best place for a vacation, great view from the cottage.Great host and thank you very much Bill for the Christmas gift."
United States
Suresh Kumar B.
The price is ￥35,150
￥62,817 total
includes taxes & fees
May 1 - May 2
Lameshur Cottage's Guest House
Beach nearby

Family Glamping Site with AC

Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (34 reviews)
"Thoughtful to have bug swatters, dart boards, honor system drinks/snacks, sunscreen/bug spray. Couches/chairs/hammocks decks were great and Frisbee golf hole/discs!"
United States
Kelly
The price is ￥33,331
￥55,998 total
includes taxes & fees
Apr 30 - May 1
Family Glamping Site with AC
Aerial view

Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.0 out of 10, Wonderful, (28 reviews)
"Everything was clean and well appointed."
United States
Josh
The price is ￥10,481
￥91,487 total
includes taxes & fees
Apr 29 - Apr 30
Villa Island Paradise
Terrace/patio

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
St Thomas
9.8 out of 10, Exceptional, (50 reviews)
"One of my favorite vrbo stays, place felt very serene and relaxing, if you love being immersed in nature I would definitely book this place."
United States
Ishjah S.
The price is ￥20,413
￥39,551 total
includes taxes & fees
Apr 26 - Apr 27
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
Beach nearby, sun loungers, beach towels

Lameshur Bay Glamping Site with AC

Lameshur Bay Glamping Site with AC
St John
10.0 out of 10, Exceptional, (29 reviews)
"Really enjoyed our stay. We felt well taken care of and loved the location!"
United States
John
The price is ￥21,377
￥38,077 total
includes taxes & fees
May 1 - May 2
Lameshur Bay Glamping Site with AC
On the beach, sun loungers, beach towels

Breathtaking Views from Sapphire Village II

Breathtaking Views from Sapphire Village II
St Thomas
8.8 out of 10, Excellent, (34 reviews)
"Perfect overnight location for us. the unit is as described, the owner was responsive as we did need to contact her with a question. We were able to walk to the beach where there were restaurants and bars to enjoy :) "
United States
Darcy
The price is ￥21,530
￥45,592 total
includes taxes & fees
Apr 24 - Apr 25
Breathtaking Views from Sapphire Village II
On the beach

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address
Maho Bay Quarter
9.6 out of 10, Exceptional, (34 reviews)
"Property was excellent for a couple, exactly as described. Host was welcoming and everything was clean and in order. Location is great - a very short walk to Trunk Bay. We have stayed on St John many times and this property is perfect for two people."
United States
Erik R.
The price is ￥118,813
￥198,614 total
includes taxes & fees
May 17 - May 18
The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address
Property grounds

Salt Pond Bay Glamping Site With AC

Salt Pond Bay Glamping Site With AC
St John
10.0 out of 10, Exceptional, (7 reviews)
"rooms are new and very clean. host was present when we arrived and lives on site. nice shared kitchen area with fridge, sink, grill, dishs etc."
United States
Jim H.
The price is ￥21,377
￥38,077 total
includes taxes & fees
May 1 - May 2
Salt Pond Bay Glamping Site With AC
City Apartment, 3 Bedrooms, Kitchen, City View | Living room | 45-inch TV with digital channels, Netflix, Hulu

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 ￥34,268
￥62,464 total
includes taxes & fees
May 6 - May 7
The Landmark Apartment
Exterior

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, (858 reviews)
"Excellent stay resort was perfectly located "
United States
andrew
The price is ￥14,081
￥17,249 total
includes taxes & fees
May 2 - May 3
Flamboyan on the Bay Resort and Villas
Outdoor pool

Sapphire Beachfront, Step Right to the Beach, WIFI, Central AC, Great Views

Sapphire Beachfront, Step Right to the Beach, WIFI, Central AC, Great Views
St Thomas
9.6 out of 10, Exceptional, (7 reviews)
"The location was perfect as we were able to visit many beaches with the Jeep that we rented then would end our day at this beautiful condo on the beach. Snorkeling at Sapphire beach was amazing. "
United States
Mike W.
The price is ￥37,119
￥74,930 total
includes taxes & fees
Apr 27 - Apr 28
Sapphire Beachfront, Step Right to the Beach, WIFI, Central AC, Great Views
Beach nearby, sun loungers, beach towels

Luxury Beachside Escape with Private Pool and Generator!

Luxury Beachside Escape with Private Pool and Generator!
St Thomas
9.4 out of 10, Exceptional, (35 reviews)
"Great location and fantastic communication. "
United States
Mike J.
The price is ￥26,952
￥62,278 total
includes taxes & fees
May 7 - May 8
Luxury Beachside Escape with Private Pool and Generator!
Terrace/patio

Magens Bay - dining - POOL - Incredible views

Magens Bay - dining - POOL - Incredible views
St. Thomas
9.8 out of 10, Exceptional, (81 reviews)
"The house met every expectation. Meghan was terrific when we had a question. we all had a fabulous stay. I would really recommend this house for a holiday. However be aware there are a lot of stairs. Loved the luggage and grocery lift."
United States
Cheryl M.
The price is ￥103,171
￥262,061 total
includes taxes & fees
Apr 26 - Apr 27
Magens Bay - dining - POOL - Incredible views
Outdoor dining

Ocean and Magens Bay View NorthStar Escape

Ocean and Magens Bay View NorthStar Escape
St. Thomas
10.0 out of 10, Exceptional, (21 reviews)
"The host Jamila was amazing. She is available if you need anything. The condo was very clean and in great condition. We would recommend highly as our stay was wonderful. Thank you Jamila"
United States
Jeff M.
The price is ￥29,025
￥64,230 total
includes taxes & fees
May 10 - May 11
Ocean and Magens Bay View NorthStar Escape
Terrace/patio

Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (38 reviews)
"Clean, comfortable and conveniently located to beach, ferry and restaurants."
United States
Deborah
The price is ￥21,059
￥43,149 total
includes taxes & fees
May 5 - May 6
Sophisticated Beach Condo-Ocean View-Sapphire
On the beach, sun loungers, beach towels

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, (238 reviews)
"The place was spotless "
United States
Harvey A
The price is ￥11,164
￥41,585 total
includes taxes & fees
May 19 - May 20
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
On the beach

Stunning St. Thomas Condo for Your Tropical Escape

Stunning St. Thomas Condo for Your Tropical Escape
St. Thomas
9.6 out of 10, Exceptional, (32 reviews)
"Very clean and easy to navigate. Beds were comfortable and the unit was quiet. Gorgeous view. Nice to be next to iggys and the bolongo restaurant"
United States
Kelly
The price is ￥33,586
￥104,309 total
includes taxes & fees
May 14 - May 15
Stunning St. Thomas Condo for Your Tropical Escape
Property grounds

Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!

Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!
St Thomas
10.0 out of 10, Exceptional, (95 reviews)
"What an amazing home! We absolutely loved staying here, and would definitely come back. The host was so responsive and answered all questions so quickly. The views are stunning! "
United States
Niki G.
The price is ￥85,708
￥178,837 total
includes taxes & fees
May 8 - May 9
Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!
Property grounds

Luxurious Beachfront Condo: May- August Savings!!! Paradise at your toes!

Luxurious Beachfront Condo: May- August Savings!!! Paradise at your toes!
St Thomas
9.8 out of 10, Exceptional, (248 reviews)
"Great location on island and best unit at resort. Unit was very well stocked and had everything you would need for your vacation. Host and housekeeper were very helpful and friendly. "
United States
Melanie A.
The price is ￥31,737
￥70,312 total
includes taxes & fees
Apr 28 - Apr 29
Luxurious Beachfront Condo: May- August Savings!!! Paradise at your toes!
On the beach, sun loungers, beach towels

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, (156 reviews)
"Great stay"
United States
Mauricio R.
The price is ￥15,941
￥52,207 total
includes taxes & fees
May 4 - May 5
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
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

10/10 Excellent
"The room was spacious with a beautiful view. The pools were so nice and beaches were close by with shuttles. I would stay here again. The music entertainment at night was wonderful."
Elizabeth 3-night trip
Posted 3 hours ago
Margaritaville Vacation Club - St. Thomas

Find out more about Estate Trunk Bay

Search for holiday rentals in Estate Trunk Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Estate Trunk Bay using one of the methods below:

  • View our selection of featured holiday rentals in Estate Trunk Bay
  • Use the map to find apartments and other holiday homes in the Estate Trunk Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Estate Trunk Bay while they last

Look no further and take a look at our great range of rental properties in Estate Trunk Bay!

Frequently asked questions

Can I find vacation rentals in Estate Trunk Bay?

Yes, we offer vacation rentals close to well known points of interest in Estate Trunk Bay, or you can choose a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Estate Trunk Bay?

The Cottage at Villa Indigo: This vacation home rental outside Estate Trunk Bay is located in the mountains and offers a private yard, Netflix, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave.

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. Magens Bay Beach and Cinnamon Bay are a couple of places you'll find in the larger area.

What are vacation rentals like in Estate Trunk Bay?

Vacation rentals are privately owned properties you can book for a short or long stay in Estate Trunk Bay. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.