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Anna's Retreat Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Anna's Retreat vacation rentals

Property grounds
Bed and Shower stop

Bed and Shower stop

Bed and Shower stop
2.0 star property
St.Thomas
10.0 out of 10, Exceptional, (1)
"PERFECT ACCOMMODATIONS!!!SUPER HELPFUL HOSTS!!!.5 STARS ALL THE WAY.:)))"
United States
Jacoline C.
The price is ￥11,297
￥15,847 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Bed and Shower stop
Beach
5 ★ Sapphire Blue Horizon - Direct Ocean Front at Sapphire Beach Resort & Marina

5 ★ Sapphire Blue Horizon - Direct Ocean Front at Sapphire Beach Resort & Marina

5 ★ Sapphire Blue Horizon - Direct Ocean Front at Sapphire Beach Resort & Marina
2.0 star property
St. Thomas
10.0 out of 10, Exceptional, (143)
"Great location, attentive host with great communication, and very clean property!"
United States
Alec L.
5 ★ Sapphire Blue Horizon - Direct Ocean Front at Sapphire Beach Resort & Marina
Interior
Caribbean Retreat

Caribbean Retreat

Caribbean Retreat
Charlotte Amalie
7.8 out of 10, Good, (7)
"nice"
United States
Kathleen A.
The price is ￥47,070
￥125,206 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Caribbean Retreat
Beach
Cozy 1BR & 1 Bathroom - Private entrance

Cozy 1BR & 1 Bathroom - Private entrance

Cozy 1BR & 1 Bathroom - Private entrance
St.Thomas
2.0 out of 10, (1)
The price is ￥15,690
￥18,828 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy 1BR & 1 Bathroom - Private entrance
Beach nearby
Family Glamping Site with AC

Family Glamping Site with AC

Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (30)
"Overall great property only semi complaint which is more needy than anything is the tent will get a bit stuffy and hot when the fans die. "
United States
Will C.
The price is ￥25,414
￥43,104 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Family Glamping Site with AC
Beach nearby, sun loungers, beach towels
Lameshur Bay Glamping Site with AC

Lameshur Bay Glamping Site with AC

Lameshur Bay Glamping Site with AC
St John
10.0 out of 10, Exceptional, (23)
"Great stay! "
United States
Alex
The price is ￥22,574
￥38,016 total
includes taxes & fees
Dec 24 - Dec 25
Lameshur Bay Glamping Site with AC
Property grounds
Salt Pond Bay Glamping Site With AC

Salt Pond Bay Glamping Site With AC

Salt Pond Bay Glamping Site With AC
St John
The price is ￥21,040
￥37,477 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Salt Pond Bay Glamping Site With AC
Exterior
Flamboyan on the Bay Resort and Villas

Flamboyan on the Bay Resort and Villas

Flamboyan on the Bay Resort and Villas
3.5 star property
St. Thomas
8.6 out of 10, Excellent, (807)
"The staff was pleasant"
United States
Carla
The price is ￥21,040
￥25,774 total
includes taxes & fees
Dec 25 - Dec 26
Flamboyan on the Bay Resort and Villas
On the beach, sun loungers, beach towels
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

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, (222)
"Clean, quiet, convenient location. Perfect stay!!!"
United States
Glenda
The price is ￥3,155
￥31,156 total
includes taxes & fees
Dec 30 - Dec 31
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
Aerial view
Villa Island Paradise

Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.2 out of 10, Wonderful, (7)
"Very safe and secure place! Also very clean! Just uphill from cruz bay "
United States
Tyler
The price is ￥13,093
￥96,506 total
includes taxes & fees
Dec 24 - Dec 25
Villa Island Paradise
City Apartment, 3 Bedrooms, Kitchen, City View | Living room | 45-inch TV with digital channels, Netflix, Hulu
The Landmark Apartment

The Landmark Apartment

The Landmark Apartment
2.5 star property
St. Thomas
8.8 out of 10, Excellent, (15)
"I loved the historic nature of the building. It had an interesting layout, but it was very spacious and clean, and had a wonderful location for walking around downtown and seeing the sights."
United States
Mercy
The price is ￥34,893
￥62,790 total
includes taxes & fees
Dec 28 - Dec 29
The Landmark Apartment
Beach nearby
Lameshur Cottage's Guest House

Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (133)
"Absolutely would stay here again. We had zero issues with our stay. "
United States
Mark P.
The price is ￥37,623
￥65,830 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Lameshur Cottage's Guest House
Terrace/patio
Shibui Cove

Shibui Cove

Shibui Cove
2.0 star property
St. Thomas
10.0 out of 10, Exceptional, (1)
"I had a great stay here. The view was absolutely stunning. Being up on the side of the mountain was great. Very private but less than 5 min away from town. I will definitely stay again. "
United States
Adam R
The price is ￥29,815
￥60,186 total
includes taxes & fees
Dec 30 - Dec 31
Shibui Cove
Exterior detail
Paradise near Limetree Beach

Paradise near Limetree Beach

Paradise near Limetree Beach
St Thomas
9.6 out of 10, Exceptional, (13)
"This stay was very nice, the view was amazing,"
United States
Brandon r.
The price is ￥20,475
￥41,343 total
includes taxes & fees
Dec 29 - Dec 30
Paradise near Limetree Beach
Apartment, Ocean View | Living area
The Breeze St Thomas

The Breeze St Thomas

The Breeze St Thomas
2.0 star property
St. Thomas
The price is ￥44,136
￥77,602 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Breeze St Thomas
Cottage | 2 bedrooms, premium bedding, down comforters, pillowtop beds
The Cottage at Villa Indigo

The Cottage at Villa Indigo

The Cottage at Villa Indigo
3.0 star property
St. Thomas
8.8 out of 10, Excellent, (15)
"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 ￥40,810
￥69,606 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Cottage at Villa Indigo
Beach nearby
Stylish Beach Condo located on Sapphire Beach

Stylish Beach Condo located on Sapphire Beach

Stylish Beach Condo located on Sapphire Beach
Smith Bay
8.8 out of 10, Excellent, (18)
"Let renter know bed is raised and need to step down to get to floor. A bit of a surprise. "
United States
stuart
The price is ￥29,662
￥53,610 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Stylish Beach Condo located on Sapphire Beach
On the beach, sun loungers, beach towels
The Captain and the Mermaid - Adventures in Paradise are waiting!

The Captain and the Mermaid - Adventures in Paradise are waiting!

The Captain and the Mermaid - Adventures in Paradise are waiting!
St Thomas
9.6 out of 10, Exceptional, (207)
"Great location and amazing views."
United States
Jewel W.
The price is ￥27,606
￥52,196 total
includes taxes & fees
Dec 30 - Dec 31
The Captain and the Mermaid - Adventures in Paradise are waiting!
Terrace/patio
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
St Thomas
10.0 out of 10, Exceptional, (39)
"Clean home, accurate check-in instructions, splendid view!"
United States
Jeffrey
The price is ￥20,083
￥38,754 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
Luxury Suite Ocean View Upper 15D | View from room
Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort
4.0 star property
St. John
8.6 out of 10, Excellent, (95)
"Amazing property and helpful staff. "
United States
Joseph
The price is ￥124,736
￥170,100 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Suite St. John at Gallows Point Resort
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

Emerald Beach Resort

Emerald Beach Resort

10/10 Excellent
"Great location very close to the airport with an excellent beachfront setting. The beach is quiet in the mornings and again in the afternoons after the cruise ships leave. It’s clean and perfect for walking. The on-site restaurant is conveniently located and serves great food and cocktails. Rooms are clean and have excellent views. "
Deborah 1-night trip
Posted 3 days ago
Emerald Beach Resort

Find out more about Anna's Retreat

Search for holiday rentals in Anna's Retreat on Expedia! You can easily find your home rentals, villas, holiday apartments in Anna's Retreat using one of the methods below:

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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?

Beautiful views, walk to Secret Harbour Beach: Visitors like this Anna's Retreat vacation home rental. It is located by the ocean and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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

Expedia has 15 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. Other popular places to visit in the area include Sapphire Beach and Trunk Bay.

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.