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

Anna's Retreat Holiday Rentals

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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 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 NZ$259
includes taxes & fees
1 Oct - 2 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, (865 reviews)
"Bluebeards is one of my favorite places to stay when I am on the island."
United States
Erica
The price is NZ$405
includes taxes & fees
29 Oct - 30 Oct
Bluebeard's Castle Resort
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

3. 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, (255 reviews)
"We had an amazing time. It's highly recommended"
United States
Camierre
The price is NZ$451
includes taxes & fees
10 Oct - 11 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.

4. 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)
"We LOVED our stay and would recommend it to anyone going to St. Thomas. The location was unbeatable, and the property was equipped with everything we needed and more!"
United States
Alessandra C.
The price is NZ$455
includes taxes & fees
1 Oct - 2 Oct
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

5. 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 NZ$417
includes taxes & fees
1 Oct - 2 Oct
The Captain and the Mermaid - Adventures in Paradise are waiting!
A clear turquoise sea with people swimming.

6. 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 NZ$496
includes taxes & fees
9 Oct - 10 Oct
Breathtaking Views from Sapphire Village II
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

7. 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
9.8 out of 10, Exceptional, (203 reviews)
"Great stay! Easy to check in, communicate with host, perfect location!"
United States
Sarah L.
The price is NZ$566
includes taxes & fees
13 Oct - 14 Oct
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
An outdoor seating area with a pool view, covered by white canopies, and surrounded by potted plants.

8. 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 NZ$499
includes taxes & fees
1 Oct - 2 Oct
Sophisticated Beach Condo-Ocean View-Sapphire
A room with two wicker chairs with blue cushions, a small table with a vase, and a door with a keyhole.

9. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is NZ$569
includes taxes & fees
2 Oct - 3 Oct
The Perch at Hawk Hill
A living room with a sofa, a coffee table, a TV, and a view of the ocean through a sliding door.

10. Updated: Luxe Condo steps from Sapphire Beach!

Updated: Luxe Condo steps from Sapphire Beach!
St Thomas
9.8 out of 10, Exceptional, (98 reviews)
"Great stay, great place and great location"
United States
shane E.
The price is NZ$432
includes taxes & fees
15 Oct - 16 Oct
Updated: Luxe Condo steps from Sapphire Beach!
A coastal landscape with a beach, clear blue waters, and lush greenery.

11. 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 NZ$898
includes taxes & fees
11 Oct - 12 Oct
Villa Island Paradise
A living room with a sofa, chairs, a lamp, and a painting on the wall.

12. 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 NZ$671
includes taxes & fees
3 Oct - 4 Oct
The Landmark Apartment
A beach with clear turquoise water, sandy shore, and buildings in the background.

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

Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
St Thomas
9.8 out of 10, Exceptional, (128 reviews)
"Great place. I stay here two times a year. Always consistent. Always clean."
United States
John H.
The price is NZ$415
includes taxes & fees
4 Oct - 5 Oct
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
A beach with palm trees, clear blue sky, and a calm sea.

14. 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 NZ$404
includes taxes & fees
7 Oct - 8 Oct
Sapphire Village Large Studio/ WiFi /No Excess Owner Fees #312
A beach with clear turquoise water, sandy shore, and buildings in the background.

15. 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 NZ$533
includes taxes & fees
12 Oct - 13 Oct
Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
A beach with clear turquoise water and waves.

16. 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 NZ$456
includes taxes & fees
1 Oct - 2 Oct
The Mermaid's Pearl at Sapphire Beach
A wooden deck with outdoor furniture, including chairs and a table, under a large umbrella.

17. Hidden Hilltop Treasure

Hidden Hilltop Treasure
St. Thomas
9.8 out of 10, Exceptional, (46 reviews)
"Home was nice. "
United States
Anna L.
The price is NZ$283
includes taxes & fees
2 Oct - 3 Oct
Hidden Hilltop Treasure
A beach with clear turquoise water, a sailboat in the distance, and a blue umbrella on the sand.

18. Renovated Amazing Waterfront Escape: Balcony, Paradise At A Great Price!

Renovated Amazing Waterfront Escape: Balcony, Paradise At A Great Price!
Saint Thomas, USVI
8.6 out of 10, Excellent, (49 reviews)
"Easy short stay. Room was clean. But note the “futon” is an air bed and there were no extra sheets for it."
United States
Catherine F.
The price is NZ$579
includes taxes & fees
10 Oct - 11 Oct
Renovated Amazing Waterfront Escape: Balcony, Paradise At A Great Price!
A beach with clear turquoise water, a sailboat in the distance, and a blue umbrella on the sand.

19. Amazing Waterfront Escape: Balcony, Renovated, Paradise At A Great Price!

Amazing Waterfront Escape: Balcony, Renovated, Paradise At A Great Price!
Saint Thomas
9.2 out of 10, Wonderful, (65 reviews)
"Cozy and romantic room with an excellent air conditioner. "
United States
Matt R.
The price is NZ$606
includes taxes & fees
14 Oct - 15 Oct
Amazing Waterfront Escape: Balcony, Renovated, Paradise At A Great Price!
A beach with clear turquoise water, a sailboat in the distance, and a blue umbrella on the sand.

20. Paradise At A Great Price, Amazing Renovated Waterfront Escape: Private Balcony!

Paradise At A Great Price, Amazing Renovated Waterfront Escape: Private Balcony!
St. Thomas
8.8 out of 10, Excellent, (39 reviews)
"Property was a bit “tired” but restaurants on site were great"
United States
Rebecca K.
The price is NZ$570
includes taxes & fees
1 Oct - 2 Oct
Paradise At A Great Price, Amazing Renovated Waterfront Escape: Private Balcony!
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

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

10/10 Excellent
"We loved our stay at margaritaville! Staff was helpful and kind and it was a great experience."
Samantha Katherine 5-night trip
Posted 13 hours ago
Margaritaville Vacation Club - St. Thomas

Find out more about Anna's Retreat

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Anna's Retreat holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Anna's Retreat. 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 Anna's Retreat. Seeing all the best attractions is bound to make you fall in love with Anna's Retreat. Who knows, you may even be tempted to extend your 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 holiday 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 Anna's Retreat short-term rentals, that won’t be hard to do.

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.