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

Anna's Retreat Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

Our top choices for Anna's Retreat vacation 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
$133 nightly
The price is $147
Oct 10 - Oct 11
Total with taxes and fees
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, (890 reviews)
"Property was very clean and a beautiful place to stay."
United States
Freo
$203 nightly
The price is $228
Nov 8 - Nov 9
Total with taxes and fees
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
$559 nightly
The price is $629
Oct 16 - Oct 17
Total with taxes and fees
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
$827 nightly
The price is $912
Oct 11 - Oct 12
Total with taxes and fees
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, (508 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
$351 nightly
The price is $395
Oct 23 - Oct 24
Total with taxes and fees
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
$434 nightly
The price is $488
Oct 11 - Oct 12
Total with taxes and fees
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
$229 nightly
The price is $235
Oct 10 - Oct 11
Total with taxes and fees
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.
$229 nightly
The price is $235
Oct 16 - Oct 17
Total with taxes and fees
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
$295 nightly
The price is $314
Oct 10 - Oct 11
Total with taxes and fees
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
$236 nightly
The price is $262
Oct 11 - Oct 12
Total with taxes and fees
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.
$294 nightly
The price is $311
Oct 10 - Oct 11
Total with taxes and fees
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.
$228 nightly
The price is $240
Oct 10 - Oct 11
Total with taxes and fees
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.
$286 nightly
The price is $302
Oct 10 - Oct 11
Total with taxes and fees
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.
$800 nightly
The price is $888
Nov 3 - Nov 4
Total with taxes and fees
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.
$478 nightly
The price is $530
Oct 10 - Oct 11
Total with taxes and fees
1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level
A beach with palm trees, sun loungers, and a building in the background.

17. Beach Resort Walk-Out Patio with St. John Views

Beach Resort Walk-Out Patio with St. John Views
St Thomas
10.0 out of 10, Exceptional, (101 reviews)
"Great location"
United States
Jacqueline
$423 nightly
The price is $448
Oct 10 - Oct 11
Total with taxes and fees
Beach Resort Walk-Out Patio with St. John Views
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
$271 nightly
The price is $286
Oct 10 - Oct 11
Total with taxes and fees
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.
$223 nightly
The price is $235
Oct 12 - Oct 13
Total with taxes and fees
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.
$290 nightly
The price is $290
Oct 12 - Oct 13
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anna's Retreat Hotel Reviews

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

10/10 Excellent
"This property has gorgeous views from all around the property. It does not sit right on a beach, but there is one next door at the sister property (Buoy House) which has a shuttle to take you down or you can take the stairs. Everyone was very friendly and helpful. The swim up bar was convenient and fun to grab a drink and look out at the ocean from the infinity pool. The gift shop/cafe has great coffee made to order. I definitely would stay again. It was a great vacation!"
Jane Eggers 5-night trip
Posted less than an hour ago
The Westin St. Thomas Beach Resort & Spa

Find out more about Anna's Retreat

Everything you need to know about Anna's Retreat vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Anna's Retreat vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Anna's Retreat vacation 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 low season months. For more hustle and bustle, you may prefer to visit Anna's Retreat in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $228 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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 vacation rentals in Anna's Retreat?

Yes, you can find vacation rentals close to the most popular local attractions in Anna's Retreat, or you can select a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Anna's Retreat?

Mampoo Hill-- a Beachfront House 60 feet from the Ocean with optional Jeep: You might want to consider this vacation home rental near Anna's Retreat, which is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a selection of games and a hot tub.

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

Expedia has 13 vacation 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 larger area.

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

A vacation rental is a private property you can book for a few weeks or just a few days in Anna's Retreat. Vacation rentals offer amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.