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

Anna's Retreat Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Anna's Retreat vacation rentals

A small, simple room with a bed, a mirror, a window with a curtain, and a view of the outside.

1. Relaxed Island Living Cottage

Relaxed Island Living Cottage
Annas Retreat
The price is CA $232
CA $292 total
includes taxes & fees
Nov 6 - Nov 7
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, (918 reviews)
"Property was very clean and a beautiful place to stay."
United States
Freo
The price is CA $171
CA $211 total
includes taxes & fees
Nov 24 - Nov 25
Bluebeard's Castle Resort
A coastal resort with beachfront villas, a golf course, and lush greenery.

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, (258 reviews)
"We had an amazing time. It's highly recommended"
United States
Camierre
The price is CA $42
CA $290 total
includes taxes & fees
Oct 29 - Oct 30
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
A swimming pool with lounge chairs and thatched umbrellas.

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, (203 reviews)
"Great place to stay and peaceful"
United States
Candice D.
The price is CA $98
CA $361 total
includes taxes & fees
Nov 6 - Nov 7
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A beachfront hotel with multiple buildings, a sandy beach, and rocky shoreline.

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, (244 reviews)
"Great clean and safe place to stay"
United States
angela C.
The price is CA $145
CA $344 total
includes taxes & fees
Oct 31 - Nov 1
The Captain and the Mermaid - Adventures in Paradise are waiting!
A round wooden dining table set for six with wicker chairs, a vase of yellow flowers, and a hanging light fixture.

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 CA $192
CA $790 total
includes taxes & fees
Oct 31 - Nov 1
Villa Island Paradise
A beachside restaurant with a view of the sea, wooden tables, and a tiled floor.

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
9.6 out of 10, Exceptional, (174 reviews)
"Excellent location and very nice place to visit and Sudi's Bar/restaurant is the place to be and the whole staff is Excellent and the food is delicious and reminds you of Cheers 😎."
United States
Quincy
The price is CA $140
CA $459 total
includes taxes & fees
Nov 1 - Nov 2
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
A bedroom with a bed, a desk, a chair, a ceiling fan, and a balcony with a view.

8. 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 CA $155
CA $373 total
includes taxes & fees
Oct 26 - Oct 27
The Mermaid's Pearl at Sapphire Beach
A poolside area with lounge chairs and tables, a pool, and surrounding greenery.

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 CA $221
CA $440 total
includes taxes & fees
Oct 26 - Oct 27
Breathtaking Views from Sapphire Village II
A resort with a central pool, palm trees, and a view of the ocean.

10. 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, (510 reviews)
"Everything was amazing! It will always be my go to when I come to visit."
United States
Treacy
The price is CA $548
CA $616 total
includes taxes & fees
Nov 7 - Nov 8
The Westin St. John Resort Villas
A wooden deck with lounge chairs and a pool, overlooking a body of water with boats and a mountainous backdrop.

11. Villa East - Panoramic waterfront view - Best location

Villa East - Panoramic waterfront view - Best location
6600 Estate Smith Bay, East End
9.6 out of 10, Exceptional, (52 reviews)
"Room was very clean and the staff at the resort were very helpful and friendly. The view was incredible!"
United States
Konner
The price is CA $139
CA $548 total
includes taxes & fees
Nov 23 - Nov 24
Villa East - Panoramic waterfront view - Best location
A balcony with a herringbone floor, a wicker chair, a small table, and a view of a coastal area with palm trees and a boat.

12. 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 CA $200
CA $566 total
includes taxes & fees
Oct 30 - Oct 31
Amazing Waterfront Escape: Balcony, Renovated, Paradise At A Great Price!
A bedroom with a bed, a nightstand with a vase of flowers, and a wall with a textured pattern.

13. Updated: Luxe Condo steps from Sapphire Beach!

Updated: Luxe Condo steps from Sapphire Beach!
St Thomas
9.6 out of 10, Exceptional, (99 reviews)
"Great stay, great place and great location"
United States
shane E.
The price is CA $150
CA $384 total
includes taxes & fees
Nov 9 - Nov 10
Updated: Luxe Condo steps from Sapphire Beach!
A balcony with wicker furniture and a glass table, overlooking a coastal area with palm trees and a clear blue sky.

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 CA $203
CA $458 total
includes taxes & fees
Nov 3 - Nov 4
Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
An outdoor seating area with wooden tables and chairs, a covered patio, and a sandy beach in the background.

15. 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 CA $164
CA $400 total
includes taxes & fees
Oct 26 - Oct 27
Sophisticated Beach Condo-Ocean View-Sapphire
A balcony with a glass table and wicker chairs, overlooking a scenic landscape with hills and a body of water.

16. 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, (129 reviews)
"Super clean, hotness responsive. Would highly recommend"
United States
Nolan Y.
The price is CA $139
CA $331 total
includes taxes & fees
Oct 26 - Oct 27
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
A clear blue pool with lounge chairs and palm trees, surrounded by a stone wall and a view of the ocean.

17. 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 CA $284
CA $742 total
includes taxes & fees
Oct 31 - Nov 1
1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level
A wooden deck with two Adirondack chairs facing a large body of water and a distant island.

18. 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 CA $125
CA $469 total
includes taxes & fees
Oct 26 - Oct 27
Paradise At A Great Price, Amazing Renovated Waterfront Escape: Private Balcony!
A bedroom with a bed, a TV mounted on the wall, a wooden cabinet, and a kitchen area in the background.

19. 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 CA $181
CA $407 total
includes taxes & fees
Oct 27 - Oct 28
Renovated Charming Studio Retreat with Stunning Caribbean Views
Outdoor dining

20. Updated: Luxury Villa, Amazing Views with Pool + Generator

Updated: Luxury Villa, Amazing Views with Pool + Generator
Nazareth
9.6 out of 10, Exceptional, (105 reviews)
"Amazing views."
United States
Brian F.
The price is CA $137
CA $412 total
includes taxes & fees
Nov 9 - Nov 10
Updated: Luxury Villa, Amazing Views with Pool + Generator
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

Windward Passage Hotel

Windward Passage Hotel

8/10 Good
"Short trip no complaints"
Raheem 2-night trip
Posted 3 hours ago
Windward Passage Hotel

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna's Retreat vacation rentals we have selected for you start as low as CA $211 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 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.