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, (41 reviews)
"View was amazing . Unit itself was very unique"
United States
Zach Ezekiel Azurus
The price is CA $113
CA $687 total
includes taxes & fees
Oct 11 - Oct 12
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, (507 reviews)
"Unfortunately, the pool was under construction during our stay and unusable, but we didn't allow that to stop us. The beach was quite and relaxing, thus Westin has a family vibe and good for children. The staff was friendly. I do think they can do better at advertising the water and children's activities. The rooms were excellent and resturants too. Ferry service and crew were great too. Great stay for a family of 5!"
United States
Shani
The price is CA $488
CA $549 total
includes taxes & fees
Oct 4 - Oct 5
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, (83 reviews)
"The host was great! She helped with some last minute reservation changes. This place was clean, the beds were comfy and it was close to everything. We appreciated the beach chairs and cooler for the beaches. We would stay here again!"
United States
Ashley
The price is CA $184
CA $327 total
includes taxes & fees
Sep 17 - Sep 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 $269
CA $499 total
includes taxes & fees
Sep 17 - Sep 18
Lameshur Cottage's Guest House

5. 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, (254 reviews)
"Enjoyed our stay "
United States
Jason A.
The price is CA $28
CA $269 total
includes taxes & fees
Sep 17 - Sep 18
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

6. Sunset Hideaway Suite - Oceanview/central to Cruz Bay

Sunset Hideaway Suite - Oceanview/central to Cruz Bay
St John
9.8 out of 10, Exceptional, (19 reviews)
"Clean and spacious! Great location, proximity to Cruz Bay!"
United States
Laina M.
The price is CA $332
CA $575 total
includes taxes & fees
Sep 17 - Sep 18
Sunset Hideaway Suite - Oceanview/central to Cruz Bay

7. 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 $688
CA $1,021 total
includes taxes & fees
Sep 19 - Sep 20
Suite St. John at Gallows Point 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 $124
CA $251 total
includes taxes & fees
Sep 17 - Sep 18
Flamingo Grove Glamping Site with AC

9. Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.2 out of 10, Very good, (21 reviews)
"Outstanding view from the villa"
United States
Thomas
The price is CA $869
CA $1,212 total
includes taxes & fees
Sep 22 - Sep 23
Peter Bay Gatehouse

10. Aahana Studio 4-303S

Aahana Studio 4-303S
Cruz Bay, St. John
10.0 out of 10, Exceptional, (59 reviews)
"Very clean. Great location. Helpful property manager. Great value for the money. Good sunset views. Very convenient to restaurants!"
United States
Charlene Z.
The price is CA $292
CA $812 total
includes taxes & fees
Sep 22 - Sep 23
Aahana Studio 4-303S

11. 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, (201 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 $28
CA $272 total
includes taxes & fees
Sep 22 - Sep 23
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

12. 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, (173 reviews)
"Excellent location and very nice place to visit and Sudi's Bar/restaurant is the place to be and the whole staff is Excellent and the food is delicious and reminds you of Cheers 😎."
United States
Quincy
The price is CA $69
CA $363 total
includes taxes & fees
Sep 17 - Sep 18
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

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, (240 reviews)
"Stayed for two and had a great time. Location was close to many tourist spots, hiking, shopping, and entertainments."
United States
Dede C.
The price is CA $137
CA $328 total
includes taxes & fees
Sep 20 - Sep 21
The Captain and the Mermaid - Adventures in Paradise are waiting!

14. 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)
"Great place. I stay here two times a year. Always consistent. Always clean."
United States
John H.
The price is CA $132
CA $323 total
includes taxes & fees
Sep 18 - Sep 19
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

15. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (838 reviews)
"Very beautiful place to stay and peaceful"
United States
Luis
The price is CA $256
CA $317 total
includes taxes & fees
Oct 17 - Oct 18
Bluebeard's Castle Resort

16. 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
Sep 17 - Sep 18
Breathtaking Views from Sapphire Village II

17. St John Inn Boutique Hotel Suite w/ Kitchenette

St John Inn Boutique Hotel Suite w/ Kitchenette
Cruz Bay
9.8 out of 10, Exceptional, (7 reviews)
"Fantastic we'll go again! "
United States
Paul D.
The price is CA $313
CA $472 total
includes taxes & fees
Sep 30 - Oct 1
St John Inn Boutique Hotel Suite w/ Kitchenette

18. St. John Escape 4-304

St. John Escape 4-304
St. John
10.0 out of 10, Exceptional, (130 reviews)
"We had a wonderful time staying in this beautiful property while visiting St John! "
United States
Kari H.
The price is CA $417
CA $1,055 total
includes taxes & fees
Sep 17 - Sep 18
St. John Escape 4-304

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

Grande Bay Resort - Indigo Blue Luxury Studio Beachfront!
Cruz Bay
10.0 out of 10, Exceptional, (172 reviews)
"We loved Grande Bay. Communication was excellent & location was ideal"
United States
Eileen S.
The price is CA $383
CA $827 total
includes taxes & fees
Oct 16 - Oct 17
Grande Bay Resort - Indigo Blue Luxury Studio Beachfront!

20. Amazing St. John Paradise most comfortable and convenient accommodations

Amazing St. John Paradise most comfortable and convenient accommodations
St John
10.0 out of 10, Exceptional, (99 reviews)
The price is CA $376
CA $1,129 total
includes taxes & fees
Sep 23 - Sep 24
Amazing St. John Paradise most comfortable and convenient accommodations
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?

Mampoo Hill-- a Beachfront House 60 feet from the Ocean with optional Jeep: This vacation home rental outside of Estate Trunk Bay is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a selection of games and a hot tub.

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 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.