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, (36 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 $60
CA $729 total
includes taxes & fees
Aug 16 - Aug 17
Villa Island Paradise

2. 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, (501 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 $520
CA $585 total
includes taxes & fees
Sep 2 - Sep 3
The Westin St. John Resort Villas

3. 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, (82 reviews)
"Amazing host and great property!"
United States
Stephanie K.
The price is CA $184
CA $327 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Island Studio-5 Mins to Cruz Bay & Beaches

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 $270
CA $494 total
includes taxes & fees
Aug 23 - Aug 24
Lameshur Cottage's Guest House

5. 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 $145
CA $341 total
includes taxes & fees
Aug 17 - Aug 18
Flamingo House • PALM • Sunset view • Walk to town

6. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (733 reviews)
"The view, the accommodation, the staff were all superb. I always stay there when I visit the Island."
United States
Janice
The price is CA $257
CA $346 total
includes taxes & fees
Sep 12 - Sep 13
Bluebeard's Castle Resort

7. 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, (175 reviews)
"Good location. "
United States
Anonymous traveller
The price is CA $84
CA $382 total
includes taxes & fees
Aug 17 - Aug 18
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

8. 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 CA $690
CA $1,019 total
includes taxes & fees
Aug 22 - Aug 23
Suite St. John at Gallows Point Resort

9. 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 CA $313
CA $888 total
includes taxes & fees
Sep 5 - Sep 6
Sunset Ridge Villas Unit D

10. 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 $124
CA $251 total
includes taxes & fees
Aug 23 - Aug 24
Flamingo Grove Glamping Site with AC

11. 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, (251 reviews)
"Enjoyed our stay "
United States
Jason A.
The price is CA $125
CA $396 total
includes taxes & fees
Sep 3 - Sep 4
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

12. 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)
"Clean and spacious! Great location, proximity to Cruz Bay!"
United States
Laina M.
The price is CA $333
CA $577 total
includes taxes & fees
Aug 16 - Aug 17
Sunset Hideaway Suite - Oceanview/central to Cruz Bay

13. 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, (236 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 $150
CA $348 total
includes taxes & fees
Aug 20 - Aug 21
The Captain and the Mermaid - Adventures in Paradise are waiting!

14. Aahana Studio 4-303S

Aahana Studio 4-303S
Cruz Bay, St. John
10.0 out of 10, Exceptional, (58 reviews)
"4th time staying here. Great experience as always!"
United States
Glenn L.
The price is CA $293
CA $810 total
includes taxes & fees
Aug 18 - Aug 19
Aahana Studio 4-303S

15. 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 $871
CA $1,215 total
includes taxes & fees
Aug 17 - Aug 18
Peter Bay Gatehouse

16. 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 $221
CA $397 total
includes taxes & fees
Aug 22 - Aug 23
Turtle Nest Family Glamping Site with AC

17. 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)
"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 CA $125
CA $396 total
includes taxes & fees
Sep 3 - Sep 4
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

18. 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 CA $188
CA $395 total
includes taxes & fees
Aug 17 - Aug 18
Breathtaking Views from Sapphire Village II

19. 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)
"Room was just what we needed. Easy to check in and out. Good location near Sapphire Beach and some restaurants. It is a good hill so walking back is tougher but manageable for me and my 12 year old. "
United States
Nicole C.
The price is CA $138
CA $329 total
includes taxes & fees
Aug 22 - Aug 23
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

20. Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312

Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
St Thomas
9.6 out of 10, Exceptional, (94 reviews)
"Great location! The beach chairs and cooler were a nice bonus. The resort has a nice pool -- small, but clean and with several chairs and a restroom/changing room. Would definitely stay here again. "
United States
Steph M.
The price is CA $132
CA $325 total
includes taxes & fees
Aug 21 - Aug 22
Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
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. 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.