Annaberg Plantation showing a ruin and heritage elements

Estate Annaberg holiday lettings

We found 2,650 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

August 2025

September 2025

Discover a selection of holiday rentals in Estate Annaberg that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, such as air conditioning and a TV. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Estate Annaberg

Showing deals for:7 Nov - 14 Nov

Exceptional

(88 reviews)

New home, Privately nestled w/ your own pool and spectacular views! Backup Power

St. John, St John

8% off

£480 per night

includes taxes & fees

Come Spoil Yourself at Spirit on the Water!

Exceptional

(39 reviews)

Private cliffside retreat full of magic. 10 bedrooms, 22 beds - infinity pool.

St. Thomas, Virgin Island

8% off

£2,913 per night

includes taxes & fees

private pool in secluded 1 bedroom nestled next to the national park

Exceptional

(94 reviews)

“Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”

St. John, US Virgin Islands

8% off

£240 per night

includes taxes & fees

Unobstructed view of Smith Bay National Park from your deck.

Exceptional

(78 reviews)

Gorgeous view of St. John and BVI. Luxury bed. New floor & kitchen.

St. Thomas, St Thomas

7% off

£185 per night

includes taxes & fees

Beautiful remodeled pool with glass tile and graduated steps for easy access.

Exceptional

(18 reviews)

Privacy. Romantic Private Pool Villa @ Sapphire. Generator

Red Hook, St Thomas

7% off

£213 per night

includes taxes & fees

Exceptional

(30 reviews)

The View at Sapphire Beach- Beachfront Property at SBCW Crystal Cove

St. Thomas, Virgin Islands

9% off

£235 per night

includes taxes & fees

Beautiful Sapphire Beach with its amazing view at St.John & tranquil atmosphere!

Exceptional

(29 reviews)

1 bedroom Crystal Cove condo on Sapphire Beach. Gated community, private beach.

Red Hook, St Thomas

7% off

£256 per night

includes taxes & fees

Exceptional

(8 reviews)

spacious and cozy 1 bedroom with garden views and AC-1 mile from Cruz Bay

St. John, St John

8% off

£177 per night

includes taxes & fees

Exceptional

(9 reviews)

2bed 2bath with a shared Pool and a View. 7 mins to Cruz Bay! 15 mins to Beaches

St. John

8% off

£362 per night

includes taxes & fees

Exceptional

(116 reviews)

Sunny Summer Special- 1BR Sleeps 4 /Sapphire H/S WIFI /No Excess Owner Fees

Red Hook, VI

7% off

£179 per night

includes taxes & fees

Exceptional

(59 reviews)

Red Hook - 2 bedroom private villa and pool on the east end of St. Thomas, USVI

St. Thomas, St Thomas

7% off

£531 per night

includes taxes & fees

Morning pic of Villa de La Vista, your studio enjoys the deck on the lower right

Exceptional

(90 reviews)

One Bedroom studio on Atlantic ocean with trade winds and views

St. Thomas, St Thomas

7% off

£118 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Estate Annaberg

The view from the deck across to the National Park, with Tortola in the distance

Walk To St. John's Beautiful North Shore Beaches!Newly Renovated/AirConditioned

Sleeps 6 · 3 bedrooms · 4 bathrooms

Short walk to world-famous Maho Bay amid the pristine National Park.

Walk to world famous Maho Bay! Privacy, views, pool, 4 equal king size bedrooms.

Sleeps 8 · 4 bedrooms · 4+ bathrooms

View from the road of Maho Bay Beach Villa

NEW! MAHO BAY BEACH VILLA ST. JOHN USVI LESS THAN A 30 SECOND WALK TO THE BEACH.

Sleeps 6 · 2 bedrooms · 2 bathrooms

Top rated rentals - Estate Annaberg

Premier Host

AMAZING VIEWS FROM VILLA CELESTE

As the title suggests the view from the Villa is stunning. The property itself is very well appointed - the bedroom/living area is pleasant and airy, there is an excellent bathroom with large walk in shower and separate large laundry/storage area. The cosy kitchen is very well equipped and accommodated our dining in when it was too windy to sit out. The vast patio area has an excellent and well maintained bbq and plenty of quality furniture. Access to the Villa with its fabulous position requires a jeep or similar (Lois made this clear to us) as the approach road is very steep. Walking to and from Coral Bay is not an option. As keen walkers, the remoteness did not suit us as much as it will undoubtedly suit others. Having said that, we’re pleased we rented Villa Celeste, had a wonderful time and shall return to St John.

Tom W.

Stayed Feb 2025

Premier Host

So near the beach

We enjoyed our stay, it was just what we were looking for. Close to the beach and Good snorkeling.

susan and Elihu c.

Stayed Mar 2024

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Find out more about Estate Annaberg

Choose a holiday rental for your Estate Annaberg getaway

Learn about the unique charm of Estate Annaberg with a stay in a holiday home rental. This city has something for everyone. Sapphire Beach and Magens Bay Beach are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Estate Annaberg

Are you hoping to find attractions to see in the city? Venture out of your holiday home and experience everything that Estate Annaberg has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

Mahogany Run Golf Course (11.2 mi / 18 km)
The Self Centre (3.6 mi / 5.7 km)

Exploring the natural landscape of Estate Annaberg

Whether you're an adventurous traveller or just want to appreciate the scenery, Estate Annaberg is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

Sapphire Beach (7.8 mi / 12.6 km)
Magens Bay Beach (12.5 mi / 20.2 km)
Maho Beach (0.9 mi / 1.4 km)
Virgin Islands National Park (1.5 mi / 2.5 km)
Cinnamon Bay Beach (1.7 mi / 2.7 km)
Cinnamon Bay (1.7 mi / 2.8 km)

Transport options to and around Estate Annaberg

The nearest airport is in St. Thomas (SPB-St. Thomas Seaplane Base), located 13.7 mi (22 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Tortola (EIS-Terrance B. Lettsome Intl.), which is 14.1 mi (22.7 km) away.

Frequently asked questions

What is the best area to stay in Estate Annaberg when booking a holiday rental?

When considering a holiday rental in Estate Annaberg, one of the most appealing areas to stay is the vicinity of the Annaberg Sugar Plantation. This charming neighbourhood not only offers stunning views of the surrounding landscape but also immerses visitors in the rich history of the U.S. Virgin Islands. The plantation itself is a top attraction, showcasing the island's sugar production heritage and providing an insight into the local culture through its well-preserved ruins. Staying nearby allows easy access to the beautiful Annaberg Beach, where you can enjoy sunbathing or snorkelling in the crystal-clear waters.

How much does it cost to rent a holiday home in Estate Annaberg?

Prices for holiday rentals in Estate Annaberg 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 Annaberg 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 Annaberg holiday house rentals?

You can find great discounts on house rentals in Estate Annaberg 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 holiday rentals in Estate Annaberg?

A long-stay holiday rental in Estate Annaberg is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Are there any Estate Annaberg holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Estate Annaberg with parking available—perfect for families or travellers 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.

What are popular rental amenities in Estate Annaberg?

In Estate Annaberg, holiday rentals typically offer a variety of amenities that enhance the tropical experience. Most properties feature outdoor spaces such as patios or balconies, allowing guests to enjoy the stunning views of the Caribbean Sea. Many rentals come equipped with kitchens, enabling visitors to prepare their own meals and dine al fresco. Additionally, air conditioning is a common amenity, providing comfort in the warm climate. Some properties may also include access to shared pools or private beach access, making them ideal for relaxing after a day of exploring the nearby Virgin Islands National Park or enjoying the local beaches.

How early should I book a Estate Annaberg holiday rental?

Book your Estate Annaberg holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Can I change or cancel my Estate Annaberg home rental booking on Vrbo?

To find Estate Annaberg holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

Are all fees included in the Estate Annaberg holiday 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.