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. 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, (258 reviews)
"We had an amazing time. It's highly recommended"
United States
Camierre
The price is CA $84
CA $343 total
includes taxes & fees
Nov 2 - Nov 3
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

2. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (932 reviews)
"Staff, Food, everything was great!"
United States
Puthearin
The price is CA $248
CA $306 total
includes taxes & fees
Dec 1 - Dec 2
Bluebeard's Castle Resort

3. 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 $125
CA $705 total
includes taxes & fees
Nov 2 - Nov 3
Villa Island Paradise

4. 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, (512 reviews)
"Everything was amazing! It will always be my go to when I come to visit."
United States
Treacy
The price is CA $546
CA $615 total
includes taxes & fees
Nov 17 - Nov 18
The Westin St. John Resort Villas

5. 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, (203 reviews)
"Great place to stay and peaceful"
United States
Candice D.
The price is CA $84
CA $343 total
includes taxes & fees
Nov 6 - Nov 7
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

6. 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, (245 reviews)
"Great clean and safe place to stay"
United States
angela C.
The price is CA $161
CA $364 total
includes taxes & fees
Nov 10 - Nov 11
The Captain and the Mermaid - Adventures in Paradise are waiting!

7. 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 $220
CA $401 total
includes taxes & fees
Nov 2 - Nov 3
Breathtaking Views from Sapphire Village II

8. 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, (97 reviews)
"Safire Condos and beach are great. Host were amazing, promptly responding to any messages. Short 5 minute walk to one of the best beaches, clean, not crowded, and outstanding food and drink options."
United States
Chamberlain
The price is CA $164
CA $367 total
includes taxes & fees
Nov 7 - Nov 8
Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312

9. Charming Beach Condo w/ Balcony

Charming Beach Condo w/ Balcony
Smith Bay
9.4 out of 10, Exceptional, (48 reviews)
"Beautiful room, beach was great, good location."
United States
Justina o.
The price is CA $238
CA $470 total
includes taxes & fees
Nov 10 - Nov 11
Charming Beach Condo w/ Balcony

10. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (164 reviews)
"Great spot and excellent host"
United States
amanda c.
The price is CA $154
CA $373 total
includes taxes & fees
Nov 7 - Nov 8
The Mermaid's Pearl at Sapphire Beach

11. Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (45 reviews)
"Clean room, AC worked great, pool is very close. Overall, a really cool place to stay."
United States
Michael
The price is CA $164
CA $381 total
includes taxes & fees
Nov 3 - Nov 4
Sophisticated Beach Condo-Ocean View-Sapphire

12. 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 $901
CA $1,274 total
includes taxes & fees
Nov 2 - Nov 3
Suite St. John at Gallows Point Resort

13. Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
St. Thomas
9.8 out of 10, Exceptional, (144 reviews)
"We had an amazing stay, the condo was very clean and close to several beaches and restaurants."
United States
Jessica D.
The price is CA $222
CA $482 total
includes taxes & fees
Nov 7 - Nov 8
Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

14. Luxury Private Pool Villa. Grill. Generator@Sapphire

Luxury Private Pool Villa. Grill. Generator@Sapphire
Red Hook
9.6 out of 10, Exceptional, (18 reviews)
"Had a great stay, will definitely be back!"
United States
Madison C.
The price is CA $283
CA $655 total
includes taxes & fees
Nov 14 - Nov 15
Luxury Private Pool Villa. Grill. Generator@Sapphire

15. 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, (129 reviews)
"Super clean, hotness responsive. Would highly recommend"
United States
Nolan Y.
The price is CA $183
CA $392 total
includes taxes & fees
Nov 7 - Nov 8
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

16. Sapphire Beach Escape -Top Floor- Amazing Views- Walk to Beach/Restaurants- HGTV

Sapphire Beach Escape -Top Floor- Amazing Views- Walk to Beach/Restaurants- HGTV
St Thomas
10.0 out of 10, Exceptional, (13 reviews)
"Great spot! Well stocked, good view, hard to beat"
United States
John S.
The price is CA $162
CA $368 total
includes taxes & fees
Nov 4 - Nov 5
Sapphire Beach Escape -Top Floor- Amazing Views- Walk to Beach/Restaurants- HGTV

17. Renovated Charming Studio Retreat with Stunning Caribbean Views

Renovated Charming Studio Retreat with Stunning Caribbean Views
St Thomas
9.8 out of 10, Exceptional, (22 reviews)
"it was excellent!"
United States
Sam F.
The price is CA $264
CA $477 total
includes taxes & fees
Nov 3 - Nov 4
Renovated Charming Studio Retreat with Stunning Caribbean Views

18. 1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level

1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level
St Thomas
9.8 out of 10, Exceptional, (160 reviews)
"Perfect room for our vacation! Close enough to the sapphire beach restaurant and pool but far enough away to still be quiet at night. "
United States
Michelle M.
The price is CA $409
CA $859 total
includes taxes & fees
Nov 11 - Nov 12
1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level

19. Updated: Luxe Condo steps from Sapphire Beach!

Updated: Luxe Condo steps from Sapphire Beach!
St Thomas
9.6 out of 10, Exceptional, (99 reviews)
"Great location and close to lots of beaches and ferry to St John."
United States
Jeff B.
The price is CA $162
CA $365 total
includes taxes & fees
Nov 26 - Nov 27
Updated: Luxe Condo steps from Sapphire Beach!

20. Octopus Den Glamping Site with AC

Octopus Den Glamping Site with AC
St John
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful experience with clean and comfortable room."
United States
Peiming
The price is CA $162
CA $287 total
includes taxes & fees
Nov 2 - Nov 3
Octopus Den Glamping Site with AC
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 Gibney 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.