Estate Trunk Bay Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Estate Trunk Bay vacation rentals

Aerial view

Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (31 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
$503 nightly
The price is $563
Jun 28 - Jun 29
Total with taxes and fees
Villa Island Paradise
Beach nearby

Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (141 reviews)
"Amazing location and so peaceful. Will be coming back!!"
United States
Bob C.
$336 nightly
The price is $360
Jun 6 - Jun 7
Total with taxes and fees
Lameshur Cottage's Guest House
Beach nearby, sun loungers, beach towels

Lameshur Bay Glamping Site with AC

Lameshur Bay 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
$222 nightly
The price is $239
Jun 6 - Jun 7
Total with taxes and fees
Lameshur Bay Glamping Site with AC
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, (890 reviews)
"beautiful location coffee shop and restaurant was delicious"
United States
Kayli
$98 nightly
The price is $109
Jun 16 - Jun 17
Total with taxes and fees
Flamboyan on the Bay Resort and Villas
Property grounds

Salt Pond Bay Glamping Site With AC

Salt Pond Bay Glamping Site With AC
St John
10.0 out of 10, Exceptional, (8 reviews)
"Emily & Bill are great hosts & have the wonderful ability to be attentive to guests while providing a peaceful & relaxed atmosphere where you know they’re on property, yet giving everyone their personal space. "
United States
William C.
$222 nightly
The price is $239
Jun 6 - Jun 7
Total with taxes and fees
Salt Pond 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, (36 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
$269 nightly
The price is $286
Jun 8 - Jun 9
Total with taxes and fees
Breathtaking Views from Sapphire Village II
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, (245 reviews)
"We were impressed with the room and its location. Had everything we needed for our brief stay. Appreciated the king sized bed after several days of much smaller ones. In great walking proximity to Sapphire Bay Beach and its restaurants and coffee shop."
United States
Roxanne
$252 nightly
The price is $261
Jun 11 - Jun 12
Total with taxes and fees
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
On the beach, sun loungers, beach towels

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, (228 reviews)
"Host was great! Super responsive and accommodating to our early check in needs. "
United States
Susanne M.
$232 nightly
The price is $244
Jun 6 - Jun 7
Total with taxes and fees
The Captain and the Mermaid - Adventures in Paradise are waiting!
Terrace/patio

Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (41 reviews)
"We stayed just one night before heading over to St. John. The room was clean and suited our needs well. It was nice to have an on site restaurant, Sudi's, that provided a fun start to our trip"
United States
Marshall
$255 nightly
The price is $272
Jun 7 - Jun 8
Total with taxes and fees
Sophisticated Beach Condo-Ocean View-Sapphire
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
$325 nightly
The price is $351
Jun 6 - Jun 7
Total with taxes and fees
Family Glamping Site with AC
Beach nearby

Charming Beach Condo w/ Balcony

Charming Beach Condo w/ Balcony
Smith Bay
9.4 out of 10, Exceptional, (46 reviews)
"We spent five days at the beginning of May 2026 in this condo and couldn’t ask for a better spot for our first trip to St. Thomas! Perfect location ..close to Red Hook for shops and the ferry. Nice balcony for watching the sunrise and coffee. Pool was refreshing and maintained regularly. Local restaurant / bar, Sudi’s, located in the lower level of building. Provides laid back island vibes with great drinks and delicious food. Host was accommodating and responsive when needed. Would definitely...
United States
Catherine
$277 nightly
The price is $296
Jun 9 - Jun 10
Total with taxes and fees
Charming Beach Condo w/ Balcony
Beach

Studio Double @ WorldMark Elysian Beach Resort

Studio Double @ WorldMark Elysian Beach Resort
St Thomas
9.6 out of 10, Exceptional, (4 reviews)
"Facilities were nice and check in easy. We enjoyed our stay."
United States
Joe L.
$466 nightly
The price is $466
Jun 10 - Jun 11
Total with taxes and fees
Studio Double @ WorldMark Elysian Beach Resort
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
$376 nightly
The price is $404
Jun 9 - Jun 10
Total with taxes and fees
The Landmark Apartment
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, (55 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.
$222 nightly
The price is $237
Jun 17 - Jun 18
Total with taxes and fees
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
On the beach, sun loungers, beach towels

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, (194 reviews)
"Excellent location. The kitchen had everything we needed, and the view was excellent."
United States
Jessica M.
$252 nightly
The price is $261
Jun 16 - Jun 17
Total with taxes and fees
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
Beach nearby, sun loungers, beach towels

The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (156 reviews)
"The condo was very nice and clean with a great view & lots of beach gear. Everything worked except the pool nearest to us was closed."
United States
Suzanne
$245 nightly
The price is $272
Jun 8 - Jun 9
Total with taxes and fees
The Mermaid's Pearl at Sapphire Beach
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.
$360 nightly
The price is $381
Jun 8 - Jun 9
Total with taxes and fees
Ocean and Magens Bay View NorthStar Escape
Interior

Cozy stay, next to lookout and 10 minutes for Magens Bay Beach

Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
St. Thomas
8.8 out of 10, Excellent, (18 reviews)
"The view and apartment was amazing we will definitely be returning in the future!"
United States
Jennifer
$398 nightly
The price is $398
Jun 7 - Jun 8
Total with taxes and fees
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
Outdoor dining

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, (78 reviews)
"The view is beautiful and the room was really clean "
United States
Lynn M.
$245 nightly
The price is $245
Jul 5 - Jul 6
Total with taxes and fees
Cozy Island Studio-5 Mins to Cruz Bay & Beaches
On the beach

Amazing View: 1 Bed/1 Bath Villa on Red Hook strip

Amazing View: 1 Bed/1 Bath Villa on Red Hook strip
United States Virgin Islands
9.6 out of 10, Exceptional, (17 reviews)
"We had a great stay here! Beautiful view from patio and clean place. "
United States
Eliza
$303 nightly
The price is $303
Jun 8 - Jun 9
Total with taxes and fees
Amazing View: 1 Bed/1 Bath Villa on Red Hook strip
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

Secret Harbour Beach Resort

Secret Harbour Beach Resort

10/10 Excellent
"I read the reviews before choosing this location, and I can honestly say they were absolutely true. The staff exceeded my expectations, and I could not have been more pleased with the care, professionalism, and service I received. I highly recommend them to anyone looking for a positive experience."
Media L 5-night trip
Posted 2 hours ago
Secret Harbour Beach Resort

Find out more about Estate Trunk Bay

Everything you need to know about Estate Trunk Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Estate Trunk Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Estate Trunk Bay vacation 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 low season months. For more hustle and bustle, you may prefer to visit Estate Trunk Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $109 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Estate Trunk Bay rentals

At Expedia, we put the best Estate Trunk Bay vacation 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 vacation.

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 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?

Gorgeous View, Beach Access, Swimming Pool, Kayaks, Quiet Privacy - the East End: This vacation home rental outside of Estate Trunk Bay is located in the mountains and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You can relax into your vacation 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 Virgin Islands National Park. Sapphire 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.