A beach with kayaks and a clear blue sea.

Estate Smith Bay Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Estate Smith Bay holiday rentals

A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

1. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (763 reviews)
"Great entertainment in the evenings and the pool bar area is wonderful"
United States
Shannon
The price is S$290
includes taxes & fees
22 Sept - 23 Sept
Bluebeard's Castle Resort
A tropical beach with clear turquoise waters, white sand, and lush greenery.

2. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (37 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 S$698
includes taxes & fees
26 Aug - 27 Aug
Villa Island Paradise
A resort with a central pool, palm trees, and a view of the ocean.

3. 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, (503 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 S$501
includes taxes & fees
6 Sept - 7 Sept
The Westin St. John Resort Villas
A living room with a sofa, chairs, a lamp, and a painting on the wall.

4. The Landmark Apartment

The Landmark Apartment
2.5 star property
St. Thomas
8.6 out of 10, Excellent, (18 reviews)
"Wonderful place to stay and Ali the cab driver was also amazing "
United States
Eileen
The price is S$476
includes taxes & fees
25 Aug - 26 Aug
The Landmark Apartment
A room with a TV, wicker furniture, and a view of the ocean.

5. 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 S$933
includes taxes & fees
25 Aug - 26 Aug
Suite St. John at Gallows Point Resort
A spacious living area with a sofa, dining table, and chairs, overlooking a scenic ocean view.

6. The Breeze

The Breeze
2.0 star property
ST Thomas
The price is S$943
includes taxes & fees
25 Aug - 26 Aug
The Breeze
A balcony with a view of a coastal town, a table, and a chair.

7. Little Indigo Apartments

Little Indigo Apartments
3.5 star property
St. Thomas
7.8 out of 10, Good, (30 reviews)
"The apartment had an amazing view. It was clean and well prepared prior to our arrival. I look forward to our next visit."
United States
Lynda
The price is S$394
includes taxes & fees
25 Aug - 26 Aug
Little Indigo Apartments
A bedroom with a bed, a nightstand, a lamp, and a view through a door.

8. Aqua

Aqua
3.0 star property
St. Thomas
9.4 out of 10, Exceptional, (8 reviews)
"Comfortable and beautiful area"
United States
Paola
The price is S$473
includes taxes & fees
26 Aug - 27 Aug
Aqua
A balcony with two wicker chairs and a small round table, surrounded by a white railing, overlooking a lush green landscape with hills in the background.

9. 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 S$452
includes taxes & fees
25 Aug - 26 Aug
Villa Indigo 1BR in Private Gated Estate
Two people seated at a table with a view of the sea and greenery.

10. Shibui Cove

Shibui Cove
2.0 star property
St. Thomas
7.4 out of 10, Good, (6 reviews)
"Not everything was operational in the apt. Lights/fans etc. but was an awesome place to stay."
United States
William Eric
The price is S$305
includes taxes & fees
4 Sept - 5 Sept
Shibui Cove
A bedroom with a bed, a chair, a nightstand, a lamp, and a window with blinds.

11. The Cottage at Villa Indigo

The Cottage at Villa Indigo
3.0 star property
St. Thomas
8.8 out of 10, Excellent, (15 reviews)
"We got a true dose of the life experience on the island staying here. The entire experience was MAGICAL!!!! Me and my family will most definitely staying again when we come back "
United States
Oronde
The price is S$581
includes taxes & fees
25 Aug - 26 Aug
The Cottage at Villa Indigo
A beachfront hotel with multiple colorful buildings, a sandy beach, and rows of sun loungers with umbrellas.

12. Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (205 reviews)
"The property is well maintained and comfortable. Our family enjoyed the private beach and the pool. The one on-site restaurant serves a variety of good food."
United States
Cathryn
The price is S$898
includes taxes & fees
25 Aug - 26 Aug
Marriott's Frenchman's Cove
A room with two wicker chairs with blue cushions, a small table with a vase, and a door with a keyhole.

13. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is S$436
includes taxes & fees
25 Aug - 26 Aug
The Perch at Hawk Hill
A balcony with a table, chairs, and a view of a turquoise sea and green hills.

14. 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 S$1,107
includes taxes & fees
25 Aug - 26 Aug
Peter Bay Gatehouse
A coastal resort with multiple buildings, a swimming pool, and boats in the background.

15. Sunset Ridge Villas Unit D

Sunset Ridge Villas Unit D
3.5 star property
St. John
9.4 out of 10, Exceptional, (3 reviews)
"This property was excellent especially for us a family of 4 with teenage kids. The space was great and the location was easy enough to get to. The amenities were excellent, from a fully outfitted kitchen to great beach resources such as chairs, cooler & snorkel equipment. "
United States
Jessica
The price is S$800
includes taxes & fees
5 Sept - 6 Sept
Sunset Ridge Villas Unit D
A swimming pool with lounge chairs and a view of the ocean.

16. St Thomas Cliffside Villa With Pool & Hot Tub!

St Thomas Cliffside Villa With Pool & Hot Tub!
3.5 star property
St. Thomas
The price is S$1,529
includes taxes & fees
28 Aug - 29 Aug
St Thomas Cliffside Villa With Pool & Hot Tub!
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 Smith Bay Hotel Reviews

Sapphire Beach Resort

Sapphire Beach Resort

10/10 Excellent
"Loved it"
David 4-night trip
Posted 6 days ago
Sapphire Beach Resort

Frequently asked questions

Can I find a holiday rental in Estate Smith Bay?

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

How many holiday rentals will I find in Estate Smith Bay?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Estate Smith Bay stay.

What’s there to see and do in Estate Smith Bay?

Sapphire Beach and Lindquist Beach are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include Trunk Bay and Virgin Islands National Park.

What’s a holiday rental in Estate Smith Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Estate Smith Bay. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and 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 a family trip.