A coastal landscape with a clear blue sea, green hills, and scattered buildings.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Anna's Retreat 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, (872 reviews)
"Bluebeards is one of my favorite places to stay when I am on the island."
United States
Erica
The price is ฿6,213
฿7,688 total
includes taxes & fees
1 Nov - 2 Nov
Bluebeard's Castle Resort
A beachfront hotel with multiple colorful buildings, a sandy beach, and rows of sun loungers with umbrellas.

2. Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (207 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 ฿18,820
฿21,173 total
includes taxes & fees
16 Oct - 17 Oct
Marriott's Frenchman's Cove
A room with a TV, wicker furniture, and a view of the ocean.

3. 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 ฿16,635
฿24,691 total
includes taxes & fees
3 Oct - 4 Oct
Suite St. John at Gallows Point Resort
A coastal landscape with a beach, clear blue waters, and lush greenery.

4. 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 ฿3,093
฿17,060 total
includes taxes & fees
11 Oct - 12 Oct
Villa Island Paradise
A resort with a central pool, palm trees, and a view of the ocean.

5. 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, (507 reviews)
"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!"
United States
Shani
The price is ฿11,796
฿13,270 total
includes taxes & fees
15 Oct - 16 Oct
The Westin St. John Resort Villas
A living room with a sofa, chairs, a lamp, and a painting on the wall.

6. 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 ฿7,474
฿13,449 total
includes taxes & fees
3 Oct - 4 Oct
The Landmark Apartment
A bedroom with a bed, a nightstand, a lamp, and a view through a door.

7. 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 ฿7,531
฿13,512 total
includes taxes & fees
28 Oct - 29 Oct
Aqua
A balcony with a view of a coastal town, a table, and a chair.

8. 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 ฿5,716
฿10,435 total
includes taxes & fees
4 Oct - 5 Oct
Little Indigo Apartments
A bedroom with a bed, a chair, a nightstand, a lamp, and a window with blinds.

9. 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 ฿8,454
฿14,670 total
includes taxes & fees
31 Oct - 1 Nov
The Cottage at Villa Indigo
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.

10. 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 ฿7,322
฿12,422 total
includes taxes & fees
3 Oct - 4 Oct
Villa Indigo 1BR in Private Gated Estate
A room with two wicker chairs with blue cushions, a small table with a vase, and a door with a keyhole.

11. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is ฿5,785
฿11,549 total
includes taxes & fees
3 Oct - 4 Oct
The Perch at Hawk Hill
A spacious living area with a sofa, dining table, and chairs, overlooking a scenic ocean view.

12. The Breeze

The Breeze
2.0 star property
ST Thomas
The price is ฿4,420
฿25,137 total
includes taxes & fees
3 Oct - 4 Oct
The Breeze
A balcony with a table, chairs, and a view of a turquoise sea and green hills.

13. 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 ฿21,004
฿29,300 total
includes taxes & fees
3 Oct - 4 Oct
Peter Bay Gatehouse
A swimming pool with lounge chairs and a view of the ocean.

14. 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 ฿21,508
฿38,071 total
includes taxes & fees
6 Oct - 7 Oct
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 Anna's Retreat Hotel Reviews

Windward Passage Hotel

Windward Passage Hotel

8/10 Good
"The hotel is centrally located and convenient to main town and French Town. bit of a hike to Havensight or Yacht Haven Grand but not an impossible stroll. The facility is aged and there are imperfections. Despite that the facility is clean and safe and for the price point a good stay"
Antonio 1-night trip
Posted 4 hours ago
Windward Passage Hotel

Find out more about Anna's Retreat

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Frequently asked questions

Can I find holiday rentals in Anna's Retreat?

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

How many holiday rentals will I find in Anna's Retreat?

Expedia has 13 holiday rentals for your stay in Anna's Retreat.

What’s there to see and do in Anna's Retreat?

Cultural attractions include Pistarckle Theater, whereas Virgin Islands National Park is a spot to enjoy nature. Sapphire Beach and Caribbean Genealogy Library are a couple of places you'll find in the wider area.

What’s a holiday rental in Anna's Retreat like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Anna's Retreat. Holiday rentals offer extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family getaway.