A coastal landscape with lush green hills, a bay with boats, and scattered buildings.

Estate Carolina Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Estate Carolina holiday rentals

A resort with a central pool, palm trees, and a view of the ocean.

1. 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, (509 reviews)
"Everything was amazing! It will always be my go to when I come to visit."
United States
Treacy
The price is NZ$703
includes taxes & fees
25 Oct - 26 Oct
The Westin St. John Resort Villas
A room with a TV, wicker furniture, and a view of the ocean.

2. 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
The price is NZ$1,624
includes taxes & fees
13 Oct - 14 Oct
Suite St. John at Gallows Point Resort
A coastal landscape with a beach, clear blue waters, and lush greenery.

3. 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 NZ$931
includes taxes & fees
16 Oct - 17 Oct
Villa Island Paradise
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

4. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (894 reviews)
"Property was very clean and a beautiful place to stay."
United States
Freo
The price is NZ$407
includes taxes & fees
10 Nov - 11 Nov
Bluebeard's Castle Resort
A beach with turquoise water, sandy shore, and distant mountains.

5. Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (141 reviews)
"Amazing place! Great host!!Close to Salt Pond."
United States
Shawn C.
The price is NZ$621
includes taxes & fees
21 Oct - 22 Oct
Lameshur Cottage's Guest House
A beach with turquoise water, sandy shore, and distant mountains.

6. Flamingo Grove Glamping Site with AC

Flamingo Grove Glamping Site with AC
St John
9.8 out of 10, Exceptional, (30 reviews)
"Really enjoyed our stay. We felt well taken care of and loved the location!"
United States
John
The price is NZ$321
includes taxes & fees
13 Oct - 14 Oct
Flamingo Grove Glamping Site with AC
A balcony with a table, chairs, and a view of a turquoise sea and green hills.

7. Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.2 out of 10, Very good, (21 reviews)
"Outstanding view from the villa"
United States
Thomas
The price is NZ$1,870
includes taxes & fees
13 Oct - 14 Oct
Peter Bay Gatehouse
A beach with clear turquoise water, palm trees, and a distant mountain.

8. 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.
Grande Bay SURFSIDE 1 BR Beachfront, WIFI, Great Views!
A beach with turquoise water, sandy shore, and distant mountains.

9. Turtle Nest Family Glamping Site with AC

Turtle Nest Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful property and a fun experience! Would stay again."
United States
Carlee D.
The price is NZ$507
includes taxes & fees
13 Oct - 14 Oct
Turtle Nest Family Glamping Site with AC
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

10. 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 NZ$410
includes taxes & fees
23 Oct - 24 Oct
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
A clear turquoise sea with people swimming.

11. 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 NZ$542
includes taxes & fees
22 Oct - 23 Oct
Breathtaking Views from Sapphire Village II
A resort with a pool, a bridge, and a view of the ocean.

12. Gallows Point 10A, Ocean Front Elegance - 5-Star Amenities

Gallows Point 10A, Ocean Front Elegance - 5-Star Amenities
Cruz Bay
9.8 out of 10, Exceptional, (34 reviews)
"a beautiful place to stay for vacation"
United States
Xiaojiang
The price is NZ$1,922
includes taxes & fees
13 Oct - 14 Oct
Gallows Point 10A, Ocean Front Elegance - 5-Star Amenities
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.
The price is NZ$417
includes taxes & fees
16 Oct - 17 Oct
The Captain and the Mermaid - Adventures in Paradise are waiting!
A beach with clear turquoise water, palm trees, and a distant island.

14. The Peter Bay 1BR Honeymoon Suite at St. John's Most Prestigious Address

The Peter Bay 1BR Honeymoon Suite at St. John's Most Prestigious Address
Maho Bay Quarter
9.8 out of 10, Exceptional, (30 reviews)
"get ready to enjoy amazing views, bring your silky robe with which to enjoy the amazing breeze, very private deck, quiet and peaceful, feel like you are in a historic building with amazing architecture, great nights sleep, gorgeous views, wonderful costumer service with property manager, don't think twice book this villa"
United States
Tara C.
The price is NZ$2,167
includes taxes & fees
18 Oct - 19 Oct
The Peter Bay 1BR Honeymoon Suite at St. John's Most Prestigious Address
A balcony with a view of a marina and a hillside.

15. The Palms III 3-304

The Palms III 3-304
St. John
10.0 out of 10, Exceptional, (24 reviews)
"Great location overlooking Cruz Bay . Close to everything in Cruz Bay and a short drive to all the north shore beaches . We have stayed in a couple of locations in St John's . If you want to be close to the restaurants you really can't beat this location . "
United States
Joe M.
The price is NZ$1,907
includes taxes & fees
31 Oct - 1 Nov
The Palms III 3-304
A covered outdoor area with a table and chairs, a view of the sea, and potted plants.

16. St. John Escape 4-304

St. John Escape 4-304
St. John
10.0 out of 10, Exceptional, (130 reviews)
"We had a wonderful time staying in this beautiful property while visiting St John! "
United States
Kari H.
The price is NZ$1,315
includes taxes & fees
17 Oct - 18 Oct
St. John Escape 4-304
A beach with clear turquoise water, a sandy shore, and a distant island with buildings.

17. 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.
The price is NZ$412
includes taxes & fees
19 Oct - 20 Oct
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A beach with clear turquoise water and waves.

18. 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 NZ$457
includes taxes & fees
13 Oct - 14 Oct
The Mermaid's Pearl at Sapphire Beach
A restaurant with outdoor seating, palm trees, and a mountain in the background.

19. Octopus Den Glamping Site with AC

Octopus Den Glamping Site with AC
St John
10.0 out of 10, Exceptional, (8 reviews)
"Great for a short stay!"
United States
Kimberly J.
The price is NZ$321
includes taxes & fees
13 Oct - 14 Oct
Octopus Den Glamping Site with AC
A pool area with lounge chairs and a small pavilion.

20. Gone Coastal Grande Bay~Rarely Available~Oceanview~Walk to Town & Beaches

Gone Coastal Grande Bay~Rarely Available~Oceanview~Walk to Town & Beaches
Cruz Bay
10.0 out of 10, Exceptional, (125 reviews)
"Wonderful property cant wait to come back!"
United States
Valerie P.
The price is NZ$2,642
includes taxes & fees
5 Nov - 6 Nov
Gone Coastal Grande Bay~Rarely Available~Oceanview~Walk to Town & Beaches
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 Estate Carolina Hotel Reviews

Buoy Haus Beach Resort St. Thomas, Autograph Collection

Buoy Haus Beach Resort St. Thomas, Autograph Collection

10/10 Excellent
"Beautiful location! Amazing island"
Alexandria 5-night trip
Posted 4 hours ago
Buoy Haus Beach Resort St. Thomas, Autograph Collection

Find out more about Estate Carolina

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Estate Carolina holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Estate Carolina. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Estate Carolina. Seeing all the best attractions is bound to make you fall in love with Estate Carolina. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Estate Carolina short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Estate Carolina?

Yes, there are holiday rentals close to the most popular sights in Estate Carolina, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Estate Carolina has to offer?

"Someday Soon" Has Arrived!: This highly rated holiday home rental in Estate Carolina is located in the mountains, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Estate Carolina?

Choose from 44 Expedia holiday rentals in Estate Carolina for a memorable holiday.

What can I see and do in Estate Carolina?

Virgin Islands National Park and Ajax Peak are a couple of lovely local spots to get outside and enjoy nature. Mamey Peak and Sapphire Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Estate Carolina?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Estate Carolina. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family trip.