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

Holiday Rentals in Estate Trunk Bay

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Our top choices for Estate Trunk Bay holiday rentals

1. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (41 reviews)
"Such an amazing place to stay at St. Johns. Very clean, comfortable and cool. Balcony was exceptional and they had snorkeling gear which was so cool! Will definitely return. This was our 2nd time at st . John's"
United States
Angelo
The price is €402
includes taxes & fees
13 Sept - 14 Sept
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, (505 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 €340
includes taxes & fees
23 Sept - 24 Sept
The Westin St. John Resort Villas

3. 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 €195
includes taxes & fees
10 Sept - 11 Sept
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

4. 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)
"Very nice property, great communication and easy in/out."
United States
JIm B.
The price is €195
includes taxes & fees
11 Sept - 12 Sept
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

5. 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 €209
includes taxes & fees
11 Sept - 12 Sept
Cozy Island Studio-5 Mins to Cruz Bay & Beaches

6. 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 €316
includes taxes & fees
10 Sept - 11 Sept
Lameshur Cottage's Guest House

7. 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 €159
includes taxes & fees
10 Sept - 11 Sept
Flamingo Grove Glamping Site with AC

8. 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 €750
includes taxes & fees
10 Sept - 11 Sept
Peter Bay Gatehouse

9. 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 €632
includes taxes & fees
10 Sept - 11 Sept
Suite St. John at Gallows Point Resort

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 €171
includes taxes & fees
30 Sept - 1 Oct
Octopus Den Glamping Site with AC

11. 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, (176 reviews)
"Good location. "
United States
Anonymous traveller
The price is €254
includes taxes & fees
30 Sept - 1 Oct
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

12. Turtle Nest Family Glamping Site with AC

Turtle Nest Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful property and a fun experience! Would stay again."
United States
Carlee D.
The price is €249
includes taxes & fees
10 Sept - 11 Sept
Turtle Nest Family Glamping Site with AC

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, (238 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 €211
includes taxes & fees
12 Sept - 13 Sept
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 €211
includes taxes & fees
17 Sept - 18 Sept
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

15. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (163 reviews)
"The Mermaid’s Pearl was a comfortable fit for my son (19) and me. It is located in a quiet complex with a beautiful view from the balcony. The studio is a perfect size for two people and was very clean. We enjoyed the local restaurant (Sudi’s) and the pool just outside the front door, as well as the short walk to the Safire Beach complex (local coffee shop and eateries on the beach). We also walked into Red Hook which took about 20 minutes. Red Hook is small but has plenty of little shops and...
United States
Melissa
The price is €230
includes taxes & fees
10 Sept - 11 Sept
The Mermaid's Pearl at Sapphire Beach

16. Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (43 reviews)
"Clean, comfortable and conveniently located to beach, ferry and restaurants."
United States
Deborah
The price is €251
includes taxes & fees
10 Sept - 11 Sept
Sophisticated Beach Condo-Ocean View-Sapphire

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 €290
includes taxes & fees
30 Sept - 1 Oct
St John Inn Boutique Hotel Suite w/ Kitchenette

18. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (826 reviews)
"Beautiful property our family loved our stay here"
United States
Tricia
The price is €196
includes taxes & fees
8 Oct - 9 Oct
Bluebeard's Castle Resort

19. 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, (96 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 €207
includes taxes & fees
10 Sept - 11 Sept
Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312

20. 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 €252
includes taxes & fees
17 Sept - 18 Sept
Breathtaking Views from Sapphire Village II
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

Everything you need to know about Estate Trunk Bay holiday rentals

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

Estate Trunk Bay holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Estate Trunk Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Estate Trunk Bay holiday rentals we have selected for you start as low as €196 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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 holiday rentals in Estate Trunk Bay?

Yes, there are holiday rentals close to the most popular sights in Estate Trunk Bay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Estate Trunk Bay has to offer?

Mampoo Hill-- a Beachfront House 60 feet from the Ocean with optional Jeep: This holiday home rental outside of Estate Trunk Bay is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 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 wider area.

What are holiday rentals like in Estate Trunk Bay?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Estate Trunk Bay. Holiday rentals offer amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for small groups.