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Featured Holiday Homes in Anguilla

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!
Welches Home - 10 Min to Shoal Bay Beach

Welches Home - 10 Min to Shoal Bay Beach

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 National Trust of Anguilla.
Opens in a new windowWelches Home - 10 Min to Shoal Bay Beach
Charming 1 bedroom house in delightful The Valley, Anguilla.

Charming 1 bedroom house in delightful The Valley, Anguilla.

Anguilla Quarter
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 windowCharming 1 bedroom house in delightful The Valley, Anguilla.
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Stunning Ocean Front Shoal Bay Villa

Stunning Ocean Front Shoal Bay Villa

The Valley
Located in Shoal Bay, this vacation home is by the ocean, a 1-minute drive from Shoal Bay Beach and 6 minutes from Scilly Cay.
Opens in a new windowStunning Ocean Front Shoal Bay Villa
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
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
Beach access with a relaxed seaside atmosphere.

Beach access with a relaxed seaside atmosphere.

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 windowBeach access with a relaxed seaside atmosphere.
Your Dream Home Awaits: 3-Bedroom Retreat, Close to Everything

Your Dream Home Awaits: 3-Bedroom Retreat, Close to Everything

Cauls Bottom The Valley
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 windowYour Dream Home Awaits: 3-Bedroom Retreat, Close to Everything
Spectacular home - 5 mins walk to beach, modern, comfortable, clean and spacious

Spectacular home - 5 mins walk to beach, modern, comfortable, clean and spacious

The Valley Anguilla
With a stay at this vacation home 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 windowSpectacular home - 5 mins walk to beach, modern, comfortable, clean and spacious
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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
45 Holiday Homes
Lowest Price
AU$370
Highest Price
AU$2,933
Popular accommodation
Zen is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!, Welches Home - 10 Min to Shoal Bay Beach, Charming 1 bedroom house in delightful The Valley, Anguilla. , Stunning Ocean Front Shoal Bay Villa, DragonFly Studio, a charming place dedicated to relaxation, White Sands Anguilla, Beach access with a relaxed seaside atmosphere. , Your Dream Home Awaits: 3-Bedroom Retreat, Close to Everything , Spectacular home - 5 mins walk to beach, modern, comfortable, clean and spacious

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$2,768 per night from 12 Apr to 13 Apr
AU$2,768
12 Apr - 13 Apr
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
The price is AU$370 per night from 1 Apr to 2 Apr
AU$370
1 Apr - 2 Apr
includes taxes & fees
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
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$2,933 per night from 16 Apr to 17 Apr
AU$2,933
16 Apr - 17 Apr
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 Cove Bay.
Opens in a new windowCap Juluca, A Belmond Hotel, Anguilla
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Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay Rendezvous Bay
Fully refundableReserve now, pay when you stay
The price is AU$2,326 per night from 13 Apr to 14 Apr
AU$2,326
13 Apr - 14 Apr
includes taxes & fees
Located in Rendezvous Bay, Aurora Anguilla Resort & Golf Club is by the ocean, a 5-minute drive from Sandy Island and 8 minutes from Blowing Point Ferry ...
Opens in a new windowAurora Anguilla Resort & Golf Club
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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.