Estate Trunk Bay Vacation Rentals

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Our top choices for Estate Trunk Bay vacation rentals

Flamboyan on the Bay Resort and Villas

Flamboyan on the Bay Resort and Villas
3.5 star property
St. Thomas
8.6 out of 10, Excellent, (896 reviews)
"beautiful location coffee shop and restaurant was delicious"
United States
Kayli
Flamboyan on the Bay Resort and Villas

The Westin St. John Resort Villas

The Westin St. John Resort Villas
4.5 star property
St. John
8.2 out of 10, Very good, (491 reviews)
"Great unit, clean, updated and comfortable. Laundry and coffee were a plus. The resort is beautifully maintained and landscaped."
United States
Lindsay
The price is CA $1,020
CA $1,148 total
includes taxes & fees
Jul 5 - Jul 6
The Westin St. John Resort Villas

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, (105 reviews)
"Everything was just first class!!! Amazing place and great people!"
United States
Grady
The price is CA $693
CA $1,024 total
includes taxes & fees
Jul 13 - Jul 14
Suite St. John at Gallows Point Resort

Hidden Hilltop Treasure

Hidden Hilltop Treasure
Charlotte Amalie
9.6 out of 10, Exceptional, (45 reviews)
"We stayed at HiddenHilltop for about 12 hours due to scheduling problems getting to St. John on the car ferry. The owner was very helpful. Iwould have loved to spend more time there."
United States
Nancy P.
The price is CA $138
CA $239 total
includes taxes & fees
Jun 22 - Jun 23
Hidden Hilltop Treasure

Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (31 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 $75
CA $766 total
includes taxes & fees
Jun 23 - Jun 24
Villa Island Paradise

Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (141 reviews)
"Amazing location and so peaceful. Will be coming back!!"
United States
Bob C.
The price is CA $271
CA $503 total
includes taxes & fees
Jun 22 - Jun 23
Lameshur Cottage's Guest House

Lazy Loft: Tiny Room Loft Queen w Pool

Lazy Loft: Tiny Room Loft Queen w Pool
St Thomas
10.0 out of 10, Exceptional, (13 reviews)
"Room was exactly as described. Cute..small...but who needs more than a bed and a fridge in paradise. Amenities of facility having beach chairs and snorkeling gear for patrons to use saved tons of money at beaches that charge big fees for that stuff. Highly recommend staying here for anyone traveling alone or with one friend and a small budget."
United States
Roberta H.
The price is CA $137
CA $254 total
includes taxes & fees
Jun 22 - Jun 23
Lazy Loft: Tiny Room Loft Queen w Pool

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, (195 reviews)
"Excellent location. The kitchen had everything we needed, and the view was excellent."
United States
Jessica M.
The price is CA $56
CA $308 total
includes taxes & fees
Jun 17 - Jun 18
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

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, (164 reviews)
"Great location. Well maintained condo, near restaurants and beach (try Cinnamon Beach in St. John - the best!). "
United States
Michelle M.
The price is CA $98
CA $403 total
includes taxes & fees
Jun 17 - Jun 18
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (199 reviews)
"Amazing staff and pool. Super clean. Price of restaurant and market was very high"
United States
Nasrine
The price is CA $1,174
CA $1,321 total
includes taxes & fees
Jun 24 - Jun 25
Marriott's Frenchman's Cove

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
St Thomas
9.8 out of 10, Exceptional, (55 reviews)
"One of my favorite vrbo stays, place felt very serene and relaxing, if you love being immersed in nature I would definitely book this place."
United States
Ishjah S.
The price is CA $183
CA $352 total
includes taxes & fees
Jun 17 - Jun 18
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

Spacious 1bedroom with pool, garden views, and AC -1 mile from Cruz Bay

Spacious 1bedroom with pool, garden views, and AC -1 mile from Cruz Bay
Cruz Bay
9.6 out of 10, Exceptional, (18 reviews)
"my husband and i stayed here on our first night on the island and it was a very nice one night stay for us!"
United States
Faith D.
The price is CA $171
CA $449 total
includes taxes & fees
Jun 17 - Jun 18
Spacious 1bedroom with pool, garden views, and AC -1 mile from Cruz Bay

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, (229 reviews)
"Host was great! Super responsive and accommodating to our early check in needs. "
United States
Susanne M.
The price is CA $182
CA $391 total
includes taxes & fees
Jun 30 - Jul 1
The Captain and the Mermaid - Adventures in Paradise are waiting!

The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (158 reviews)
"Host was very courteous!! I will definitely be back!!"
United States
Tyneisha
The price is CA $166
CA $386 total
includes taxes & fees
Jun 21 - Jun 22
The Mermaid's Pearl at Sapphire Beach

Amazing View: 1 Bed/1 Bath Villa on Red Hook strip

Amazing View: 1 Bed/1 Bath Villa on Red Hook strip
United States Virgin Islands
9.6 out of 10, Exceptional, (17 reviews)
"We had a great stay here! Beautiful view from patio and clean place. "
United States
Eliza
The price is CA $161
CA $424 total
includes taxes & fees
Jun 22 - Jun 23
Amazing View: 1 Bed/1 Bath Villa on Red Hook strip

Villa Indigo 1BR in Private Gated Estate

Villa Indigo 1BR in Private Gated Estate
3.5 star property
St. Thomas
8.8 out of 10, Excellent, (33 reviews)
"Excellent place"
United States
Trent
The price is CA $293
CA $498 total
includes taxes & fees
Jun 17 - Jun 18
Villa Indigo 1BR in Private Gated Estate

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, (246 reviews)
"We were impressed with the room and its location. Had everything we needed for our brief stay. Appreciated the king sized bed after several days of much smaller ones. In great walking proximity to Sapphire Bay Beach and its restaurants and coffee shop."
United States
Roxanne
The price is CA $140
CA $418 total
includes taxes & fees
Jul 1 - Jul 2
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

Breathtaking Views from Sapphire Village II

Breathtaking Views from Sapphire Village II
St Thomas
8.8 out of 10, Excellent, (36 reviews)
"Perfect overnight location for us. the unit is as described, the owner was responsive as we did need to contact her with a question. We were able to walk to the beach where there were restaurants and bars to enjoy :) "
United States
Darcy
The price is CA $189
CA $399 total
includes taxes & fees
Jun 17 - Jun 18
Breathtaking Views from Sapphire Village II

Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.4 out of 10, Very good, (20 reviews)
"Staying at the gate house was wonderful. Walk to beach was a little longer than expected because of the sharp incline. Very nice place to stay!! "
United States
jonathan
The price is CA $875
CA $1,220 total
includes taxes & fees
Jul 11 - Jul 12
Peter Bay Gatehouse

Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!

Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!
St Thomas
10.0 out of 10, Exceptional, (100 reviews)
"Wonderful VRBO with amazing views and amenities!We could not have asked for better communication from our host Ryan & Roxy!"
United States
Lori L.
The price is CA $752
CA $1,570 total
includes taxes & fees
Jul 4 - Jul 5
Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!
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?

Gorgeous View, Beach Access, Swimming Pool, Kayaks, Quiet Privacy - the East End: This vacation home rental outside of Estate Trunk Bay is located in the mountains and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You can relax into your vacation with a garden and a selection of games.

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.