Estate Annas Retreat vacation rentals

We found 3,400 vacation rentals — enter your dates for availability
Discover a selection of 7 homes and other vacation rentals in Estate Annas Retreat that are perfect for your trip. Vacation rentals provide the amenities you need and want for your family, friends, or furry companion, such as WiFi and a fireplace. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Quick facts about Estate Annas Retreat

  • Estate Annas Retreat is known for its diverse offerings of outdoor activities, cultural experiences, and beautiful beach scenery in the U.S. Virgin Islands.
  • Sapphire Beach offers stunning shoreline views, Coki Point Beach is perfect for sunbathing and snorkeling, while Bolongo Bay invites outdoor enthusiasts to enjoy its beautiful scenery and beach activities.
  • Families can explore the St. John Eco Hike & Snorkel Adventure, trek the Francis Bay Trail, and discover the beauty of the Reef Bay Trailhead for an exciting outdoor experience.
  • Groups can explore local flavors at Market Square East, enjoy breathtaking views on the Skyride to Paradise Point, and catch a show at Pistarckle Theater for a well-rounded experience in Estate Annas Retreat.
  • The ideal time to visit Estate Annas Retreat is from December to February, with temperatures typically near 70-80°F (21-27°C) and generally clear conditions, while March to May usually sees averages around 75-85°F (24-29°C) with pleasant weather; visitor traffic peaks in March and is lowest in September.
  • Stay in St. Thomas for beaches and bays, in St. John for bays and beaches, or in Estate Smith Bay for beach activities.
  • St. Thomas is accessible via the St. Thomas Seaplane Base, located 5.7km from the city center, with a limited bus network available for getting around the area.

Holiday rentals with weekly discounts - Estate Annas Retreat

Showing deals for:Nov 6 - Nov 13

View from great room of Vista - Hans Lolik islands to the left
Tidal pool at base of cliff, facing Thatch Cay (north east).
Villa Vista atop cliff, south of Atlantic
Sunrise across main deck
Exceptional
(41 reviews)

5 bedroom Atlantic Waterfront

St. Thomas

8% off
$746
$5,223 for 7 nights
All fees included
5 bedroom Atlantic Waterfront
Outdoor entertainment area
Pool
12x40 foot heated, saltwater pool
Welcome to Villa Sol
Exceptional
(42 reviews)

Minutes from Magens Bay, gated property, large pool & outdoor entertainment area

St. Thomas

8% off
$565
$3,958 for 7 nights
All fees included
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
Incredible view of Caribbean Sea.
Airstream Glamping in style.
Exterior
Sunsets from deck.
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

8% off
$131
$918 for 7 nights
All fees included
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Pool deck (Old pool look)
Deck at night
Sunset view
Pool at night (Old pool look)
Exceptional
(70 reviews)

3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor

St. Thomas

8% off
$646
$4,524 for 7 nights
All fees included
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
Property grounds
Property grounds
Dining table with view of ocean
Panoramic views from wrap-around deck
Exceptional
(165 reviews)

Stunning Ocean Views! Walk To Beaches/Beach Bars/Restaurants

St. Thomas

8% off
$372
$2,602 for 7 nights
All fees included
Stunning Ocean Views! Walk To Beaches/Beach Bars/Restaurants
Dining
Down Island View!
Breakfast with a view!
Corner Deck
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

8% off
$507
$3,552 for 7 nights
All fees included
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Living area
Outdoor dining
Room
Outdoor dining
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

8% off
$404
$2,830 for 7 nights
All fees included
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
comfy bed pillows
Morning pic of Villa de La Vista, your studio enjoys the deck on the lower right
sleigh bed
new kitchen (2015)
Exceptional
(102 reviews)

One Bedroom studio on Atlantic ocean with trade winds and views

St. Thomas

8% off
$144
$1,005 for 7 nights
All fees included
One Bedroom studio on Atlantic ocean with trade winds and views
Room
Exterior
Property grounds
Property grounds
Exceptional
(18 reviews)

"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.

St. John

9% off
$421
$2,950 for 7 nights
All fees included
"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.
Blue-green water to immerse yourself in and forget your worries
The entrance to Sapphire Beach and Marina
King size bed
A palm tree to sit under, directly across from the patio of the unit
Exceptional
(65 reviews)

Beach, Bed and Beyond! WiFi included , New Tiled Shower!

St. Thomas

8% off
$410
$2,870 for 7 nights
All fees included
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
Bathroom
Dining
Dining
Room
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
$239
$1,671 for 7 nights
All fees included
Oceanfront Sunrise Escape + Backup Power & 3 Pools
Driveway approaching parking area just south of the villa.
Sunsi Bay, beach
Sugar-like sand on pocket beach at nearby Sunsi Bay
Gated entrance to Villa Vista
Exceptional
(46 reviews)

Two Bedroom Unit on the Atlantic with Trade Winds, Views

St. Thomas

8% off
$267
$1,866 for 7 nights
All fees included
Two Bedroom Unit on the Atlantic with Trade Winds, Views
Panoramic view of the inside of the apartment
Entrance to the apartment
Hummingbirds flock these flowers
Overlooking the ocean
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

8% off
$357
$2,496 for 7 nights
All fees included
Affordable, oceanfront and walk to private beach gem
Terrace/patio
Exterior
Pool
Exterior
Exceptional
(20 reviews)

Home with panoramic views with access to private beach!

St. Thomas

9% off
$1,649
$11,546 for 7 nights
All fees included
Home with panoramic views with access to private beach!
Beach
Outdoor dining
Property grounds
Property grounds
Exceptional
(9 reviews)

Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!

St. Thomas

8% off
$273
$1,913 for 7 nights
All fees included
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
Dining
Room
Room
Living area
Exceptional
(14 reviews)

Stylish Suite💎 ❤️of Downtown AC WiFi 10 minute drive to 🏖 Historical area

St. Thomas

8% off
$174
$1,219 for 7 nights
All fees included
Stylish Suite💎 ❤️of Downtown AC WiFi 10 minute drive to 🏖 Historical area
Bedroom desk area
Warm water, a cool breeze and a great view!
View of condo from front door entrance.
Bedroom area with smart TV.
Exceptional
(215 reviews)

37 Steps to the Sea – Oceanfront Ground Floor Paradise w/Backup Generator.

St. Thomas

8% off
$310
$2,171 for 7 nights
All fees included
37 Steps to the Sea – Oceanfront Ground Floor Paradise w/Backup Generator.
Main bedroom 2 ( upstairs)
Main bedroom 1
Main Bedroom 1 (downstairs) King size mattress
Main bedroom 1 bathroom
Exceptional
(23 reviews)

Villa Mangorosa

St. Thomas

9% off
$765
$5,353 for 7 nights
All fees included
Villa Mangorosa
Living area
Property grounds
Living area
Interior
Exceptional
(5 reviews)

The Ampersand Sky Villa: Iconic, Artful Luxury

St. Thomas

13% off
$519
$3,633 for 7 nights
All fees included
The Ampersand Sky Villa: Iconic, Artful Luxury
Interior
Living Room
Sapphire Beach!
Beach
Exceptional
(12 reviews)

Sapphire Beach Resort Rental

St. Thomas

20% off
$596
$4,169 for 7 nights
All fees included
Sapphire Beach Resort Rental
Property grounds
Beach
Pool
Pool
Exceptional
(101 reviews)

Sapphire Dominica-Gorgeous View Walk to beach

St. Thomas

8% off
$236
$1,650 for 7 nights
All fees included
Sapphire Dominica-Gorgeous View Walk to beach
Living area
Interior
Room
Living area
Exceptional
(12 reviews)

Luxe Loft ❤️ of Downtown AC WiFi 5 minute 🚶🏽‍♀️to beautiful waterfront 🚤

St. Thomas

8% off
$229
$1,605 for 7 nights
All fees included
Luxe Loft ❤️ of Downtown AC WiFi 5 minute 🚶🏽‍♀️to beautiful waterfront 🚤
Living area
Living area
Living area
Living area
Exceptional
(8 reviews)

New central located 2BR/3BD/2BA condo gated community with 2 pools & pickleball

St. Thomas

8% off
$503
$3,524 for 7 nights
All fees included
New central located 2BR/3BD/2BA condo gated community with 2 pools & pickleball
Interior
Romantic Luxury with Endless Sapphire Beach Ocean Views in St Thomas Paradise!
Relax your days and evenings away here - can 't you hear the waves already?
Living area
Exceptional
(148 reviews)

5 ★ “Sapphire SeaView” - Direct Ocean Front at Sapphire Beach Resort & Marina

St. Thomas

8% off
$489
$3,420 for 7 nights
All fees included
5 ★ “Sapphire SeaView” - Direct Ocean Front at Sapphire Beach Resort & Marina

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Find out more about Estate Annas Retreat

Find the perfect vacation rental for your Estate Annas Retreat getaway

Learn about the unique charm of Estate Annas Retreat with a stay in a private vacation home. This city has something for everyone. Sapphire Beach and Magens Bay Beach are just a couple of the must-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Estate Annas Retreat

Are you hoping to find things to do in the city? Venture out of your vacation home and check out everything that makes Estate Annas Retreat a fun place to get away. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Mahogany Run Golf Course (1.6 mi / 2.6 km)
  • The Self Centre (6.6 mi / 10.6 km)

Exploring the natural landscape of Estate Annas Retreat

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Estate Annas Retreat is a great spot to appreciate mother nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Sapphire Beach (2.5 mi / 4.1 km)
  • Magens Bay Beach (2.8 mi / 4.5 km)
  • Trunk Bay (7.8 mi / 12.5 km)
  • Virgin Islands National Park (9.3 mi / 14.9 km)
  • Coki Point Beach (1.4 mi / 2.3 km)
  • Wyndham Sugar Bay Beach (1.5 mi / 2.4 km)

Traveling to and around Estate Annas Retreat

The nearest airport is in St. Thomas (SPB-St. Thomas Seaplane Base), located 3.5 mi (5.7 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Cyril E. King Airport (STT), which is 5.6 mi (8.9 km) away.

Frequently asked questions

What is the best area to stay in Estate Annas Retreat, U.S. Virgin Islands when booking a vacation rental?
When considering a vacation rental in Estate Annas Retreat, the surrounding areas of St. Thomas offer some fantastic options. For a vibrant setting, you might want to explore the neighborhoods near Charlotte Amalie, the capital city of the U.S. Virgin Islands. This area is rich in history and culture, featuring attractions like Fort Christian, the oldest standing structure in the Virgin Islands, and the bustling waterfront where you can find shops, restaurants, and beautiful views of the harbor.Another appealing option is the neighborhood around Red Hook, which is known for its lively nightlife and proximity to some stunning beaches. Here, you can enjoy attractions such as the nearby Sapphire Beach, superb for sunbathing and water sports, or take a ferry to the nearby British Virgin Islands for a day trip.
How much does it cost to rent a vacation home in Estate Annas Retreat?
Prices for vacation rentals in Estate Annas Retreat vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Estate Annas Retreat to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Estate Annas Retreat vacation house rentals?
You can find great discounts on house rentals in Estate Annas Retreat on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Estate Annas Retreat?
A long-stay vacation rental in Estate Annas Retreat is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Estate Annas Retreat vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Estate Annas Retreat with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
How early should I book a Estate Annas Retreat vacation rental?
Book your Estate Annas Retreat vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Estate Annas Retreat, U.S. Virgin Islands?
In Estate Annas Retreat, visitors can explore a variety of attractions that showcase the natural beauty and culture of the U.S. Virgin Islands. The nearby Magens Bay is renowned for its stunning beach, offering calm waters ideal for swimming and relaxing under the sun. Vacation rentals in this area often provide easy access to the beach, along with scenic views of the surrounding landscape.The Charlotte Amalie area, a short drive away, features historic sites like Fort Christian, the oldest standing structure in the Virgin Islands, and the bustling waterfront with shops and local eateries. For those interested in outdoor adventures, the nearby St. Thomas Skyride to Paradise Point offers breathtaking panoramic views of the island and the harbor.Additionally, the Coral World Ocean Park, located on the northeastern coast, provides unique marine experiences and is great for families looking to learn about the local sea life.
Can I change or cancel my Estate Annas Retreat home rental booking on Vrbo?
To find Estate Annas Retreat vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Estate Annas Retreat vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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