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Estate Anguilla Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Estate Anguilla holiday rentals

A coastal landscape with a beach, lush green hills, and a clear blue sky.

1. Windchime Estates

Windchime Estates
3.0 star property
Christiansted
9.0 out of 10, Wonderful, (34 reviews)
"amazing view, the interior looks better in person, and alot of local spots around."
United States
Alexis daniel
The price is NZ$326
includes taxes & fees
4 Oct - 5 Oct
Windchime Estates
A beach with clear blue water, a sandy shore, and a distant island.

2. The Cottage at Green Cay - Walk to the Beach - King Bed - AC

The Cottage at Green Cay - Walk to the Beach - King Bed - AC
Gallows Bay
10.0 out of 10, Exceptional, (1 review)
"Everything was clean and comfortable. The beach that was walking distance was quite nice to hang out at. Our hosts were attentive and responsive. The area was quiet, scenic and a easy drive to restaurants and other beaches."
United States
Patricia F.
The price is NZ$573
includes taxes & fees
9 Oct - 10 Oct
The Cottage at Green Cay - Walk to the Beach - King Bed - AC
A small room with a green wall, a window, a round table, and two chairs.

3. Quiet and cozy 2-bedroom house

Quiet and cozy 2-bedroom house
Downtown Frederiksted
The price is NZ$267
includes taxes & fees
2 Nov - 3 Nov
Quiet and cozy 2-bedroom house
A pool area with lounge chairs, a small table, and a pathway leading to a building with illuminated windows.

4. Your Caribbean home away from home

Your Caribbean home away from home
Christiansted
9.4 out of 10, Exceptional, (21 reviews)
"Perfect for my stay, good neighborhood, host was excellent at communicating, easy access"
United States
Breanna S.
The price is NZ$504
includes taxes & fees
6 Oct - 7 Oct
Your Caribbean home away from home
A small room with a sliding glass door leading to a garden, a wooden table, and a bench.

5. Buck Island Views on North Shore: Windsors Rest

Buck Island Views on North Shore: Windsors Rest
Northcentral
9.6 out of 10, Exceptional, (10 reviews)
"beautiful location and great people"
United States
Tom M.
The price is NZ$293
includes taxes & fees
4 Oct - 5 Oct
Buck Island Views on North Shore: Windsors Rest
A beach with waves at sunset, rocky formations, and a clear sky.

6. Buck Island Views on North Shore: The Mermaid

Buck Island Views on North Shore: The Mermaid
Northcentral
9.2 out of 10, Wonderful, (5 reviews)
"We enjoyed the beautiful views and breezes on the property. We wanted to get a feel for what it would be like to live on the island and it was perfect for our needs!"
United States
Amy L.
The price is NZ$319
includes taxes & fees
4 Oct - 5 Oct
Buck Island Views on North Shore: The Mermaid
A wooden deck with lounge chairs and a pool.

7. Cozy Retreat by Chenay Bay

Cozy Retreat by Chenay Bay
Chenay Bay
9.6 out of 10, Exceptional, (14 reviews)
"Everything was neat, all the necessary details to have a wonderful stay."
United States
Monica V.
The price is NZ$503
includes taxes & fees
4 Oct - 5 Oct
Cozy Retreat by Chenay Bay
A stone wall, a concrete pathway, and a white picket fence.

8. Large & Comfortable 1 Bed/Bath Guest Room on St. Croix

Large & Comfortable 1 Bed/Bath Guest Room on St. Croix
Christiansted
8.0 out of 10, Very good, (9 reviews)
"Nice quiet place to stay in a great walking neighborhood. Nice central location."
United States
Anthony B.
The price is NZ$354
includes taxes & fees
7 Oct - 8 Oct
Large & Comfortable 1 Bed/Bath Guest Room on St. Croix
A beach with clear skies and calm waters.

9. Sunset Villas "Good Morning" Tiny Home Container

Sunset Villas "Good Morning" Tiny Home Container
Frederiksted Southeast
9.6 out of 10, Exceptional, (19 reviews)
"Beautiful view, very close to beaches, overall it was a great stay."
United States
Nelicia N.
The price is NZ$340
includes taxes & fees
14 Oct - 15 Oct
Sunset Villas "Good Morning" Tiny Home Container
A swimming pool with blue lounge chairs, palm trees, and a clear sky.

10. Caribbean View Style 1 Bedroom Condo by RedAwning

Caribbean View Style 1 Bedroom Condo by RedAwning
3.0 star property
Christiansted
10.0 out of 10, Exceptional, (1 review)
"Russ is great!"
United States
Matthew
The price is NZ$868
includes taxes & fees
9 Oct - 10 Oct
Caribbean View Style 1 Bedroom Condo by RedAwning
A living room with a wooden entertainment center, a glass coffee table, and a sofa.

11. Best Buck Island Views on North Shore: The View

Best Buck Island Views on North Shore: The View
Northcentral
8.2 out of 10, Very good, (13 reviews)
"Beautiful location, property and the owner was a great wealth of information so very friendly! Would love to visit again!"
United States
Lori C.
The price is NZ$349
includes taxes & fees
4 Oct - 5 Oct
Best Buck Island Views on North Shore: The View
A spacious room with two beds, a sofa, and a wardrobe. The room has wooden flooring and a sloped ceiling with a skylight.

12. Historic Apt in Heart of Christiansted

Historic Apt in Heart of Christiansted
3.5 star property
Christiansted Historic District
9.4 out of 10, Exceptional, (20 reviews)
"Great experience all around! Easy check in and comfortable apartment!"
United States
Cecily
The price is NZ$451
includes taxes & fees
7 Oct - 8 Oct
Historic Apt in Heart of Christiansted
A wooden deck leading to a pool area with a signboard, surrounded by greenery and a clear sky.

13. Lovely 1-bedroom condo with Fresh Water Pool

Lovely 1-bedroom condo with Fresh Water Pool
Christiansted
9.2 out of 10, Wonderful, (16 reviews)
"Clean and excellent stay. Service was above and beyond"
United States
Cole S.
The price is NZ$386
includes taxes & fees
17 Oct - 18 Oct
Lovely 1-bedroom condo with Fresh Water Pool
A well-maintained garden with a statue, a curved pathway, and a two-story building with a balcony.

14. Moko Jumbie House - "Guesthouse" - Cozy 1-Bedroom

Moko Jumbie House - "Guesthouse" - Cozy 1-Bedroom
Christiansted Historic District
10.0 out of 10, Exceptional, (18 reviews)
"The room and entire complex were so clean and beautiful. Host was super accommodating and very responsive. We walked to downtown Christiansted all of the time, usually in about 10 minutes. Lots to do there but VI Heil was a great way to explore further away. Highly recommend this property."
United States
Max
The price is NZ$352
includes taxes & fees
5 Oct - 6 Oct
Moko Jumbie House - "Guesthouse" - Cozy 1-Bedroom
An indoor dining area with a bar, wooden beams, and a chalkboard sign.

15. Town Treasure - King Bed - Walkable - AC

Town Treasure - King Bed - Walkable - AC
Christiansted Historic District
8.8 out of 10, Excellent, (5 reviews)
"I have tears in my eyes writing this because we’re on the sea plane leaving st croix. I had the greatest time ever and it was mainly thanks to our stay. The accommodations were more than I ever would have expected… And we have stayed thousands of places.this was one of my favorite experiences of my life and I owe a great huge thanks to the host for all that she did for us. Thank you so much."
United States
Kate M.
The price is NZ$385
includes taxes & fees
20 Oct - 21 Oct
Town Treasure - King Bed - Walkable - AC
A statuary garden with a house featuring a grand staircase, a well-maintained lawn, and a clear sky.

16. Moko Jumbie - "Premier Suite" - Entire Condo

Moko Jumbie - "Premier Suite" - Entire Condo
Christiansted Historic District
10.0 out of 10, Exceptional, (3 reviews)
"We loved the accessability to all favoite places to visit when we stay in st. Croix. For more than 20 years and counting now."
United States
ROBERT A.
The price is NZ$425
includes taxes & fees
5 Oct - 6 Oct
Moko Jumbie - "Premier Suite" - Entire Condo
A modern kitchen with wooden cabinets, a dining area with a table and chairs, a grey sofa with patterned cushions, and a window providing natural light.

17. Romey's Villa in Gated Community

Romey's Villa in Gated Community
Christiansted
9.4 out of 10, Exceptional, (3 reviews)
"Great home, clean, plenty of towels, host was great to communicate."
United States
Kert S.
The price is NZ$672
includes taxes & fees
7 Oct - 8 Oct
Romey's Villa in Gated Community
A balcony with a view of the ocean and a distant island.

18. "Spectacular Ocean Views" at Calypso Castillo!

"Spectacular Ocean Views" at Calypso Castillo!
Sion Farm
10.0 out of 10, Exceptional, (6 reviews)
"Their property was very nice and clean and loved the area where it was located at"
United States
Stephen M T.
The price is NZ$621
includes taxes & fees
2 Nov - 3 Nov
"Spectacular Ocean Views" at Calypso Castillo!
A well-maintained garden with a central statue, a curved brick pathway, and a large tree.

19. Moko Jumbie House - "Historic Suite" A Modern 1-Bedroom Oasis.

Moko Jumbie House - "Historic Suite" A Modern 1-Bedroom Oasis.
Christiansted Historic District
9.4 out of 10, Exceptional, (9 reviews)
"Very close to town and very clean."
United States
Nicholas C.
The price is NZ$380
includes taxes & fees
4 Oct - 5 Oct
Moko Jumbie House - "Historic Suite" A Modern 1-Bedroom Oasis.
A white building with a blue roof, surrounded by lush greenery and vibrant purple flowers.

20. Private & Cozy 1 Bed/1 Bath Apartment

Private & Cozy 1 Bed/1 Bath Apartment
Christiansted
9.8 out of 10, Exceptional, (7 reviews)
"When I arrived the owner came out and showed me exactly where to go. The apartment was small but just what I needed. It was clean, smelled nice, and I appreciate the nice touch of having gentle music and scenery on the TV monitor. Great stay. A couple of unexpected, but friendly dogs were nearby, eager for a pat on the head. All good!"
United States
Sean D.
The price is NZ$424
includes taxes & fees
4 Oct - 5 Oct
Private & Cozy 1 Bed/1 Bath Apartment
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 Anguilla Hotel Reviews

The Fred - Adults Only

The Fred - Adults Only

10/10 Excellent
"Amazing place with a beautiful view and exceptional service!"
Eric 1-night trip
Posted 12 hours ago
The Fred - Adults Only

Find out more about Estate Anguilla

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 Anguilla 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 Anguilla. 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 Anguilla. Seeing all the best attractions is bound to make you fall in love with Estate Anguilla. 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 Anguilla short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Estate Anguilla?

Yes, there are holiday rentals close to the most popular sights in Estate Anguilla, 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 Anguilla has to offer?

Beachfront. Just a Few Steps to the Sand. Walk to Restaurants. Near Downtown.: This holiday home rental outside of Estate Anguilla is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Estate Anguilla?

While you're exploring the area, St. George Village Botanical Garden and Sugar Beach are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Cruzan Rum Factory and Carambola Golf Club.

What are holiday rentals like in Estate Anguilla?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Estate Anguilla. Holiday rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for small groups.