Book Holiday Homes in Anguilla

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Featured Holiday Homes in Anguilla

Paradise in Anguilla

Paradise in Anguilla

Sandy Hill
When you stay at this vacation home in The Valley, you'll be on the beach, within a 10-minute walk of Sandy Hill Bay and Sandy Hill Beach.
Opens in a new windowParadise in Anguilla
Beautiful island home modeled after traditional West Indian design

Beautiful island home modeled after traditional West Indian design

Seafeathers
When you stay at this vacation home in East End Village, you'll be on the waterfront, within a 5-minute drive of Sandy Hill Bay and Heritage Collection.
Opens in a new windowBeautiful island home modeled after traditional West Indian design
Secluded house on private beach

Secluded house on private beach

Sandy Ground
With a stay at this vacation home in The Valley (Sandy Ground), you'll be within a 10-minute drive of Blowing Point Ferry Terminal and Pelican Bay.
Opens in a new windowSecluded house on private beach
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White Sands Anguilla

White Sands Anguilla

3.5 out of 5
Cul De Sac Road Blowing Point
When you stay at White Sands Anguilla in Blowing Point, you'll be near the beach, within a 5-minute drive of Blowing Point Ferry Terminal and Pelican Bay.
Opens in a new windowWhite Sands Anguilla
The Little Villa (Newly Renovated)

The Little Villa (Newly Renovated)

anguilla
When you stay at this vacation home in The Valley, you'll be near the beach, within a 5-minute drive of LockRum Bay and Pelican Bay.
Opens in a new windowThe Little Villa (Newly Renovated)
Anguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach

Anguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach

2 out of 5
West End Anguilla
With a stay at this vacation home in West End Village, you'll be just steps from Meads Bay Pond and Meads Bay Beach.
Opens in a new windowAnguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach
Sienna is Private, Tranquil,  and Perfectly Located near Shoal Bay Beach!

Sienna is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!

Shoal Bay
With a stay at this vacation home in Island Harbour, you'll be within a 5-minute drive of Shoal Bay Beach and Scilly Cay.
Opens in a new windowSienna is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!
DragonFly Studio, a charming place dedicated to relaxation

DragonFly Studio, a charming place dedicated to relaxation

The Valley Anguilla
When you stay at this vacation home in The Valley, you'll be near the beach, within a 5-minute drive of Stone Cellar Art Gallery and Wallblake House.
Opens in a new windowDragonFly Studio, a charming place dedicated to relaxation
Zen is Private, Tranquil,  and Perfectly Located near Shoal Bay Beach!

Zen is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!

Shoal Bay
Located in Island Harbour, this vacation home is within a 5-minute drive of Shoal Bay Beach and Scilly Cay.
Opens in a new windowZen is Private, Tranquil, and Perfectly Located near Shoal Bay 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.

Anguilla Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Anguilla vacation homes are the perfect way for you to wing it.

Holiday houses in Anguilla let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Anguilla in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Anguilla adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Anguilla with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Anguilla vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Anguilla Holiday Homes essential information

Accommodation
43 Holiday Homes
Lowest Price
AU$2,684
Highest Price
AU$4,091
Popular accommodation
Paradise in Anguilla, Beautiful island home modeled after traditional West Indian design, Secluded house on private beach, White Sands Anguilla, The Little Villa (Newly Renovated), Anguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach , Sienna is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!, DragonFly Studio, a charming place dedicated to relaxation, Zen is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!

Top trending hotels in Anguilla

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
The price is AU$2,684 per night from 12 Jan to 13 Jan
AU$2,684
12 Jan - 13 Jan 2026
includes taxes & fees
When you stay at Four Seasons Resort and Residences Anguilla in West End Village, you'll be on the beach and 10.9 mi (17.6 km) from Shoal Bay Beach.
Opens in a new windowFour Seasons Resort and Residences Anguilla
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Rendezvous Bay Rendezvous Bay
With a stay at Anguilla Great House Beach Resort in Rendezvous Bay, you'll be on the beach, just a 2-minute walk from Rendezvous Bay Beach and 12 minutes by ...
Opens in a new windowAnguilla Great House Beach Resort
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Maundays Bay Maunday's Bay
The price is AU$4,091 per night from 10 Jan to 11 Jan
AU$4,091
10 Jan - 11 Jan 2026
includes taxes & fees
With a stay at Cap Juluca, A Belmond Hotel, Anguilla in Maunday's Bay, you'll be next to a golf course, just a 2-minute walk from Cove Bay and 7 minutes by foot ...
Opens in a new windowCap Juluca, A Belmond Hotel, Anguilla
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Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Malliouhana West End Village
The price is AU$2,868 per night from 3 Jan to 4 Jan
AU$2,868
3 Jan - 4 Jan 2026
includes taxes & fees
With a stay at Malliouhana Resort Anguilla in West End Village, you'll be by the ocean, just a 2-minute walk from Meads Bay Beach and 5 minutes by foot from ...
Opens in a new windowMalliouhana Resort Anguilla
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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.

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^Subject to availability and chosen travel dates.