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
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 Meads Bay and Blowing Point Ferry Terminal.
Opens in a new windowSecluded house on private beach
White Sands Anguilla

White Sands Anguilla

3.5 out of 5
Cul De Sac Road Blowing Point
With a stay at White Sands Anguilla in Blowing Point, you'll be near the beach, within a 10-minute drive of Meads Bay and Blowing Point Ferry Terminal.
Opens in a new windowWhite Sands Anguilla
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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 villa in West End Village, you'll be within a 5-minute walk of Meads Bay and Meads Bay Pond.
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
With a stay at this vacation home in The Valley, you'll be within a 15-minute drive of Meads Bay and Stone Cellar Art Gallery.
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!
Dream Weaver Villa in RendezVous Bay

Dream Weaver Villa in RendezVous Bay

RendezVous Bay AXA
With a stay at this vacation home in Rendezvous Bay, you'll be within a 5-minute drive of Meads Bay and Aurora International Golf Club.
Opens in a new windowDream Weaver Villa in RendezVous Bay
Fortune Rise. Car Rental available

Fortune Rise. Car Rental available

Mount Fortune Anguilla
Located in East End Village, this vacation home is within a 5-minute drive of Heritage Collection and Island Harbor Beach.
Opens in a new windowFortune Rise. Car Rental available
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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$3,028
Highest Price
AU$3,691
Popular accommodation
Paradise in Anguilla, Secluded house on private beach, White Sands Anguilla, 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!, Dream Weaver Villa in RendezVous Bay, Fortune Rise. Car Rental available

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$3,028 per night from 8 Feb to 9 Feb
AU$3,028
8 Feb - 9 Feb
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
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$3,691 per night from 23 Feb to 24 Feb
AU$3,691
23 Feb - 24 Feb
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, within a 5-minute drive of Meads Bay and Maundays ...
Opens in a new windowCap Juluca, A Belmond Hotel, 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, within a 10-minute drive of Meads Bay and Rendezvous Bay Beach.
Opens in a new windowAnguilla Great House Beach Resort
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La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Back Street South Hill
With a stay at La Vue Boutique Inn in South Hill (Sandy Ground), you'll be within a 10-minute drive of Meads Bay and Blowing Point Ferry Terminal.
Opens in a new windowLa Vue Boutique Inn
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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.