Anguilla Holiday Rentals

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Top Holiday Rentals Destinations in Anguilla

Turtles Nest Beach Resort 
3 out of 5
Meads Bay, West End Village, Anguilla
The price is NZ$519 per night from 19 May to 20 May
NZ$519
per night
19 May - 20 May
Stay at this 3-star beach condo in West End Village. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (100 reviews)
"This stay was perfect, location and accommodation wise. The staff were so nice. I loved everything about their beach and nearby restaurants."

Reviewed on 10 May 2024

Turtles Nest Beach Resort 
Royal Palms Hotel
3.5 out of 5
West End, South Hill
The price is NZ$296 per night from 13 May to 14 May
NZ$296
per night
13 May - 14 May
Stay at this 3.5-star aparthotel in South Hill. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Rendezvous Bay Beach and Cuisinart Resort ...
9/10 Wonderful! (37 reviews)
"The cleaning lady Mrs.Dora, was very friendly and helpful. The place is super cleaned. Thanks to her and Mrs.Mary. Excellent for the price and place."

Reviewed on 30 Apr. 2024

Royal Palms Hotel
Fountain Anguilla
3.5 out of 5
The Fountain Road, Shoal Bay
Stay at this 3.5-star condo in Shoal Bay. Enjoy a garden, laundry facilities, and concierge services. Popular attractions Shoal Bay Beach and Island Harbor Beach ...
8.4/10 Very Good! (45 reviews)
"I loved staying here. Tucked away, V idyllic, comfortable units, landscaped pool area etc. Access to beautiful Shoal Bay a few mins by foot or car (car recommended!). Front desk (Merlyn and Prudence) extremely warm and gracious as were all people working at Fountain Anguilla. Hope I get the opportunity ..."

Reviewed on 26 Jan. 2024

Fountain Anguilla
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Tranquility Beach Anguilla
3.5 out of 5
Meads Bay Beach, West End Village
Stay at this 3.5-star beach aparthotel in West End Village. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Meads Bay Pond and Meads Bay ...
9.8/10 Exceptional! (21 reviews)
"Great property and staff."

Reviewed on 7 Apr. 2024

Tranquility Beach Anguilla
Milly's Inn
2 out of 5
Shoal Bay, Shoal Bay
Stay at this apartment in Shoal Bay. Enjoy free WiFi, free parking, and a garden. Popular attractions Shoal Bay Beach and Island Harbor Beach are located ...
8.8/10 Excellent! (25 reviews)
Shoal Bay is great
"We thoroughly enjoyed our stay at Milly's Inn. Two slight drawbacks are lack of air conditioning and low water pressure. But everything else was great for our purposes. The sea breezes were fine for us in temperature that ranged from 78 at night to 82 during the day, regardless of rain. The queen ..."

Reviewed on 5 May 2024

Milly's Inn
Paradise in tranquility Anguilla
Book a stay at this beach vacation home in The Valley. Enjoy a beach locale, a garden, and patios. Popular attractions Sandy Hill Bay and Sandy Hill Beach are ...
10/10 Exceptional! (1 review)
Ideal
"This is a wonderful family oriented property with lots of space, wonderful views and all the practical amenities a family needs. Anguilla can be expensive, this property is affordable making adventuring and experiencing the wonderful people, scenery and food of the island more approachable. I recommend ..."

Reviewed on 12 Jan. 2022

Paradise in tranquility Anguilla
Villa blue in Sandy Hill Bay
Stay at this condo in The Valley. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Sandy Hill Beach and Sandy Hill Bay are located ...
9.6/10 Exceptional! (26 reviews)
"Spacious villa. Good location. Near everything you want to see or do. Beautiful pool with great lounge chairs. Property is welll kept. Joyce, the manager, was always available if needed. Very impressed with kitchen supplies and linens. Would definitely recommend and come back!"

Reviewed on 9 Apr. 2024

Villa blue in Sandy Hill Bay
CHARMING  LOCATION: NEAR THE OCEAN,
LARGE BALCONY,
PRIVATE SUNDECK,
AC & WIFI
Book a stay at this family-friendly apartment in The Valley. Enjoy free WiFi, a water park, and furnished balconies. Popular attractions Sandy Hill Beach and ...
9.6/10 Exceptional! (31 reviews)
Sandy Hill Holiday
"My Wife and I have stayed here before. Very comfortable and easy to get to. Angie, the property manager was very nice and helpful. A very minor miscommunication on my part regarding air conditioning, but it was no inconvenience at all. A pleasant stay, and we would stay again!"

Reviewed on 17 Mar. 2024

CHARMING LOCATION: NEAR THE OCEAN, LARGE BALCONY, PRIVATE SUNDECK, AC & WIFI
The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach
Stay at this apartment in Island Harbour. Enjoy free WiFi, breakfast (surcharge), and patios. Popular attractions Shoal Bay Beach and Island Harbor Beach are ...
9.6/10 Exceptional! (6 reviews)
Spacious Digs!
"Nice accommodations in a quiet part of the beautiful island!"

Reviewed on 3 Feb. 2024

The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach
Secluded house on private beach
Book a stay at this beach vacation home in The Valley. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Crocus Bay and Pelican Bay are located ...
10/10 Exceptional! (4 reviews)
Great Stay
"Had a very good time at Sandy Ground. Debbie was a great hostess and was very prompt with answers to any questions and help. The home is very clean, bright and well equipped. Several bars and restaurants very close by so fun for hanging out there."

Reviewed on 16 Feb. 2024

Secluded house on private beach
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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.

Everything you need to know about Anguilla holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anguilla holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anguilla holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Anguilla holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anguilla. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anguilla holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anguilla holiday rentals we have selected for you start as low as NZ$296 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Anguilla rentals

At Expedia, we put the best Anguilla holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Anguilla rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anguilla holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anguilla. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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