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

Estate Trunk Bay Vacation Rentals

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Our top choices for Estate Trunk Bay vacation rentals

1. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (33 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 CA $106
CA $835 total
includes taxes & fees
Aug 2 - Aug 3
Villa Island Paradise

2. 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, (80 reviews)
"Amazing host and great property!"
United States
Stephanie K.
The price is CA $185
CA $332 total
includes taxes & fees
Aug 15 - Aug 16
Cozy Island Studio-5 Mins to Cruz Bay & Beaches

3. 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, (498 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 CA $616
CA $692 total
includes taxes & fees
Sep 1 - Sep 2
The Westin St. John Resort Villas

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 CA $271
CA $502 total
includes taxes & fees
Aug 2 - Aug 3
Lameshur Cottage's Guest House

5. 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, (105 reviews)
"Everything was just first class!!! Amazing place and great people!"
United States
Grady
The price is CA $693
CA $1,025 total
includes taxes & fees
Aug 9 - Aug 10
Suite St. John at Gallows Point Resort

6. 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, (250 reviews)
"We enjoyed our stay in St Thomas a lot"
United States
Natalie O.
The price is CA $84
CA $347 total
includes taxes & fees
Aug 12 - Aug 13
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

7. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (684 reviews)
"Great place!"
United States
Amy
The price is CA $259
CA $349 total
includes taxes & fees
Aug 31 - Sep 1
Bluebeard's Castle Resort

8. 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 CA $125
CA $255 total
includes taxes & fees
Aug 4 - Aug 5
Flamingo Grove Glamping Site with AC

9. 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)
"Good location. "
United States
Anonymous traveller
The price is CA $126
CA $436 total
includes taxes & fees
Aug 2 - Aug 3
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

10. 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 CA $125
CA $255 total
includes taxes & fees
Aug 4 - Aug 5
Octopus Den Glamping Site with AC

11. 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)
"Great place to stay if you are visiting St. John! Very clean, great view from the patio and 5 min from downtown area. "
United States
Christopher
The price is CA $335
CA $583 total
includes taxes & fees
Aug 9 - Aug 10
Sunset Hideaway Suite - Oceanview/central to Cruz Bay

12. 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, (235 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 CA $180
CA $388 total
includes taxes & fees
Aug 28 - Aug 29
The Captain and the Mermaid - Adventures in Paradise are waiting!

13. 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)
"Good"
United States
Edvern
The price is CA $84
CA $347 total
includes taxes & fees
Aug 6 - Aug 7
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

14. 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 CA $875
CA $1,221 total
includes taxes & fees
Aug 2 - Aug 3
Peter Bay Gatehouse

15. 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 CA $223
CA $403 total
includes taxes & fees
Aug 4 - Aug 5
Turtle Nest Family Glamping Site with AC

16. Breathtaking Views from Sapphire Village II

Breathtaking Views from Sapphire Village II
St Thomas
8.8 out of 10, Excellent, (38 reviews)
"Had a great time. Mary was very responsive and helpful."
United States
Teresa S.
The price is CA $189
CA $400 total
includes taxes & fees
Aug 6 - Aug 7
Breathtaking Views from Sapphire Village II

17. Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated

Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated
St John
10.0 out of 10, Exceptional, (322 reviews)
"The property was close to everything. Perfect spot. People at the front lobby were wonderful. Would most certainly stay there again and recommend."
United States
Bob
The price is CA $399
CA $949 total
includes taxes & fees
Aug 19 - Aug 20
Grande Bay: Sugar N' Spice: Studio Condo Great Views & Reviews; Newly Renovated

18. 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 CA $146
CA $344 total
includes taxes & fees
Aug 24 - Aug 25
Flamingo House • PALM • Sunset view • Walk to town

19. Grande Bay Resort - Mojo Blue Luxury Studio Beachfront!

Grande Bay Resort - Mojo Blue Luxury Studio Beachfront!
Cruz Bay
10.0 out of 10, Exceptional, (210 reviews)
"Great place and location. "
United States
Kevin D.
The price is CA $347
CA $792 total
includes taxes & fees
Aug 2 - Aug 3
Grande Bay Resort - Mojo Blue Luxury Studio Beachfront!

20. Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (43 reviews)
"Swell"
United States
Chelsea
The price is CA $175
CA $367 total
includes taxes & fees
Aug 4 - Aug 5
Sophisticated Beach Condo-Ocean View-Sapphire
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

Find out more about Estate Trunk Bay

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Estate Trunk Bay. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!: This vacation home rental outside of Estate Trunk Bay is located on the beach and has a balcony, a private yard, and a barbecue grill 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. While in the area, you can also visit popular places like Sapphire Beach and Magens Bay Beach.

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.