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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Anna's Retreat holiday rentals

A modern living room with a grey sectional sofa, a small side table with a lamp, and a glass coffee table.

1. Relaxed Island Living Cottage

Relaxed Island Living Cottage
Annas Retreat
The price is £114
includes taxes & fees
9 Oct - 10 Oct
Relaxed Island Living Cottage
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

2. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (887 reviews)
"Good place to stay especially during off season"
United States
Jason
The price is £172
includes taxes & fees
6 Nov - 7 Nov
Bluebeard's Castle Resort
A beachfront hotel with multiple colorful buildings, a sandy beach, and rows of sun loungers with umbrellas.

3. 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 £476
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.

4. 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 £645
includes taxes & fees
9 Oct - 10 Oct
Suite St. John at Gallows Point Resort
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 £298
includes taxes & fees
23 Oct - 24 Oct
The Westin St. John Resort Villas
A coastal landscape with a beach, clear blue waters, and lush greenery.

6. 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 £357
includes taxes & fees
11 Oct - 12 Oct
Villa Island Paradise
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

7. 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, (256 reviews)
"We had an amazing time. It's highly recommended"
United States
Camierre
The price is £181
includes taxes & fees
11 Oct - 12 Oct
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
A beach with clear turquoise water, a sandy shore, and a distant island with buildings.

8. 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, (202 reviews)
"Great place to stay and peaceful"
United States
Candice D.
The price is £181
includes taxes & fees
9 Oct - 10 Oct
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A clear turquoise sea with people swimming.

9. 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 £221
includes taxes & fees
28 Oct - 29 Oct
Breathtaking Views from Sapphire Village II
A beach with clear turquoise water and waves.

10. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (164 reviews)
"Host was very courteous!! I will definitely be back!!"
United States
Tyneisha
The price is £202
includes taxes & fees
11 Oct - 12 Oct
The Mermaid's Pearl at Sapphire Beach
A living room with a sofa, chairs, a lamp, and a painting on the wall.

11. 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 Landmark Apartment
An aerial view of a coastal area with a beach, clear turquoise waters, and a small island with buildings.

12. Stylish Beach Condo located on Sapphire Beach

Stylish Beach Condo located on Sapphire Beach
Smith Bay
9.0 out of 10, Wonderful, (25 reviews)
"Great place to crash before heading over to St. John for our week stay. Loved that restaurants and coffee shops were in walking distance. Sapphire beach was stunning and enjoyed an evening swim there before dinner. The room was decorated beautifully and very comfortable. Would stay here again!"
United States
Jess N.
The price is £239
includes taxes & fees
9 Oct - 10 Oct
Stylish Beach Condo located on Sapphire Beach
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

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, (243 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 £185
includes taxes & fees
9 Oct - 10 Oct
The Captain and the Mermaid - Adventures in Paradise are waiting!
A beach with clear turquoise water, sandy shore, and buildings in the background.

14. Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
St. Thomas
9.8 out of 10, Exceptional, (142 reviews)
"We had an amazing stay, the condo was very clean and close to several beaches and restaurants."
United States
Jessica D.
The price is £223
includes taxes & fees
19 Oct - 20 Oct
Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
A beach with clear turquoise water, palm trees, and a distant mountain.

15. Grande Bay SURFSIDE 1 BR Beachfront, WIFI, Great Views!

Grande Bay SURFSIDE 1 BR Beachfront, WIFI, Great Views!
Cruz Bay
10.0 out of 10, Exceptional, (190 reviews)
"Loved the location and will stay there again"
United States
Mark L.
The price is £673
includes taxes & fees
3 Nov - 4 Nov
Grande Bay SURFSIDE 1 BR Beachfront, WIFI, Great Views!
A beach with clear turquoise water, gentle waves, and distant islands.

16. 1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level

1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level
St Thomas
9.8 out of 10, Exceptional, (160 reviews)
"Perfect room for our vacation! Close enough to the sapphire beach restaurant and pool but far enough away to still be quiet at night. "
United States
Michelle M.
The price is £394
includes taxes & fees
10 Oct - 11 Oct
1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level
A beach with palm trees, sun loungers, and a building in the background.

17. Sapphire Beachside walkout condo E 106

Sapphire Beachside walkout condo E 106
St Thomas
10.0 out of 10, Exceptional, (101 reviews)
"Great location"
United States
Jacqueline
The price is £357
includes taxes & fees
9 Oct - 10 Oct
Sapphire Beachside walkout condo E 106
An outdoor seating area with a pool view, covered by white canopies, and surrounded by potted plants.

18. Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (45 reviews)
"Clean room, AC worked great, pool is very close. Overall, a really cool place to stay."
United States
Michael
The price is £220
includes taxes & fees
9 Oct - 10 Oct
Sophisticated Beach Condo-Ocean View-Sapphire
A beach with palm trees, clear blue sky, and a calm sea.

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 £181
includes taxes & fees
12 Oct - 13 Oct
Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
A marina with multiple boats docked, a clear blue sky, and a distant view of a mountainous landscape.

20. Renovated Charming Studio Retreat with Stunning Caribbean Views

Renovated Charming Studio Retreat with Stunning Caribbean Views
St Thomas
9.8 out of 10, Exceptional, (22 reviews)
"it was excellent!"
United States
Sam F.
The price is £215
includes taxes & fees
19 Oct - 20 Oct
Renovated Charming Studio Retreat with Stunning Caribbean 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 Anna's Retreat Hotel Reviews

Hampton by Hilton St. Thomas

Hampton by Hilton St. Thomas

10/10 Excellent
"I wish it had a balcony to over look the harbor"
kenric 4-night trip
Posted 1 hour ago
Hampton by Hilton St. Thomas

Find out more about Anna's Retreat

Everything you need to know about Anna's Retreat 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 Anna's Retreat 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 Anna's Retreat holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Anna's Retreat holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna's Retreat. 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 Anna's Retreat 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 Anna's Retreat holiday rentals we have selected for you start as low as £172 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Anna's Retreat rentals

At Expedia, we put the best Anna's Retreat 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 Anna's Retreat 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 Anna's Retreat 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 Anna's Retreat. 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 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.

What are some of the best holiday rentals that Anna's Retreat has to offer?

Mampoo Hill-- a Beachfront House 60 feet from the Ocean with optional Jeep: This holiday home rental outside of Anna's Retreat 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.

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.