Estate Trunk Bay Vacation Rentals from $228: Search Short-Term Rentals

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Our top choices for Estate Trunk Bay vacation rentals

1. Villa Island Paradise

St. John

Zach Ezekiel Azurus

$444 nightly

Oct 11 - Oct 12

Total with taxes and fees

Outdoor pool, cabanas (surcharge), sun loungers

2. The Westin St. John Resort Villas

St. John

"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!"

Shani

$351 nightly

Oct 1 - Oct 2

Total with taxes and fees

3. Cozy Island Studio-5 Mins to Cruz Bay & Beaches

St John

Ashley

$237 nightly

Sep 19 - Sep 20

Total with taxes and fees

4. Lameshur Cottage's Guest House

St John

Shawn C.

$346 nightly

Oct 10 - Oct 11

Total with taxes and fees

On the beach, sun loungers, beach towels

5. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

St. Thomas

Jason A.

$195 nightly

Sep 20 - Sep 21

Total with taxes and fees

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

St John

Laina M.

$416 nightly

Sep 19 - Sep 20

Total with taxes and fees

Luxury Suite Ocean View Upper 15D | View from room

7. Suite St. John at Gallows Point Resort

St. John

Sean

$670 nightly

Sep 18 - Sep 19

Total with taxes and fees

Beach nearby, sun loungers, beach towels

8. Flamingo Grove Glamping Site with AC

St John

John

$171 nightly

Sep 18 - Sep 19

Total with taxes and fees

9. Peter Bay Gatehouse

Maho Bay Quarter

Thomas

$775 nightly

Sep 19 - Sep 20

Total with taxes and fees

10. Aahana Studio 4-303S

Cruz Bay, St. John

Charlene Z.

$557 nightly

Sep 19 - Sep 20

Total with taxes and fees

11. Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

St. Thomas

Alessandra C.

$195 nightly

Sep 21 - Sep 22

Total with taxes and fees

12. Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

St Thomas

Quincy

$257 nightly

Sep 18 - Sep 19

Total with taxes and fees

13. The Captain and the Mermaid - Adventures in Paradise are waiting!

St Thomas

Dede C.

$224 nightly

Sep 20 - Sep 21

Total with taxes and fees

14. Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

St Thomas

John H.

$223 nightly

Sep 18 - Sep 19

Total with taxes and fees

15. Bluebeard's Castle Resort

Charlotte Amalie

Luis

$203 nightly

Oct 17 - Oct 18

Total with taxes and fees

16. Breathtaking Views from Sapphire Village II

St Thomas

Jason

$269 nightly

Sep 18 - Sep 19

Total with taxes and fees

17. St John Inn Boutique Hotel Suite w/ Kitchenette

Cruz Bay

Paul D.

$313 nightly

Sep 30 - Oct 1

Total with taxes and fees

18. St. John Escape 4-304

St. John

Kari H.

$722 nightly

Sep 18 - Sep 19

Total with taxes and fees

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

Cruz Bay

Eileen S.

$542 nightly

Oct 16 - Oct 17

Total with taxes and fees

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

St John

Leta T.

$731 nightly

Sep 23 - Sep 24

Total with taxes and fees

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Top Estate Trunk Bay Hotel Reviews

Margaritaville Vacation Club - St. Thomas

8/10 Good

"Free shuttles to couple beaches. Unfortunately, the beach at the resort was not swimmable. The pools were great and we especially liked the upper bar & pool area. Nice resort."

The Westin St. John Resort Villas

10/10 Excellent

"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!"

The Ritz-Carlton, St. Thomas

10/10 Excellent

"The whole experience was amazing. There are so many amenities that come with your stay that it takes a few days, yes days to understand everything that is available. The staff is amazing. You can ask anyone a question about the property and they either give you the answer or know who to get you too for the answer. My favorite was the pool is open 24 hours. The night swimming was alot of fun."

Secret Harbour Beach Resort

10/10 Excellent

"We loved staying here! Exactly what we were looking for and exceeded expectations. The cove and beach were gorgeous. This side of the island is protected from the wind so it was stunning when the other side of the island was getting hit with rough waves and seaweed. There’s a small reef right off the beach so it was so easy to snorkel. The restaurant onsite was amazing and the bar was awesome just footsteps from our room. The staff were so nice and helped with calling taxis. We came in the off season so the beach was not packed at all and it felt like we had found a little slice of paradise that not many people knew about. The room was so clean and it was awesome to have a little kitchen with a full fridge. It was an easy taxi from the airport and you’re so close to red hook to jump on the ferry to St John. We definitely will be staying here again and would recommend to friends and family!"

Find out more about Estate Trunk Bay

Everything you need to know about Estate Trunk Bay vacation rentals

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

Estate Trunk Bay vacation 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 low season months. For more hustle and bustle, you may prefer to visit Estate Trunk Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $228 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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 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.

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Check prices for these dates

Our top choices for Estate Trunk Bay vacation rentals

1. Villa Island Paradise

2. The Westin St. John Resort Villas

3. Cozy Island Studio-5 Mins to Cruz Bay & Beaches

4. Lameshur Cottage's Guest House

5. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

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

7. Suite St. John at Gallows Point Resort

8. Flamingo Grove Glamping Site with AC

9. Peter Bay Gatehouse

10. Aahana Studio 4-303S

11. 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!

13. The Captain and the Mermaid - Adventures in Paradise are waiting!

14. Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

15. Bluebeard's Castle Resort

16. Breathtaking Views from Sapphire Village II

17. St John Inn Boutique Hotel Suite w/ Kitchenette

18. St. John Escape 4-304

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

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

Find vacation rentals that suit your style

Top Estate Trunk Bay Hotel Reviews

Margaritaville Vacation Club - St. Thomas

Windward Passage Hotel

St John Inn

Hampton by Hilton St. Thomas

Buoy Haus Beach Resort St. Thomas, Autograph Collection

Villa Island Paradise

The Westin St. John Resort Villas

The Ritz-Carlton, St. Thomas

Secret Harbour Beach Resort

Find out more about Estate Trunk Bay

Frequently asked questions

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