Book Holiday Homes in Island Harbour

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Featured Holiday Homes in Island Harbour

DragonFly Studio, a charming place dedicated to relaxation

DragonFly Studio, a charming place dedicated to relaxation

The Valley
When you stay at this vacation home in The Valley, you'll be near the beach, within a 5-minute drive of Old Prison and Anguillan Christian Fellowship ...
DragonFly Studio, a charming place dedicated to relaxation
Spacious quiet house seconds from the beach

Spacious quiet house seconds from the 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.
Spacious quiet house seconds from the beach
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.
Paradise in Anguilla
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Genesis Residences 
Meads Bay 1 - Downstairs Unit

Genesis Residences Meads Bay 1 - Downstairs Unit

The Cove
With a stay at this vacation home in Cove Bay, you'll be within a 10-minute walk of Meads Bay Pond and Cove Bay.
Genesis Residences Meads Bay 1 - Downstairs Unit
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.
White Sands 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 Blowing Point Ferry Terminal and Pelican Bay.
Secluded house on private beach
White Sands Anguilla - 5 minute walk to beach, spacious, modern, and clean

White Sands Anguilla - 5 minute walk to beach, spacious, modern, and clean

Cul De Sac
When you stay at this vacation home in Blowing Point, you'll be on the beach, within a 5-minute drive of Blowing Point Ferry Terminal and Pelican Bay.
White Sands Anguilla - 5 minute walk to beach, spacious, modern, and clean
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
With a stay at this vacation home in West End Village, you'll be within a 5-minute walk of Meads Bay Pond and Meads Bay.
Anguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach
Your Anguilla Home! Homeaway from home-AI

Your Anguilla Home! Homeaway from home-AI

Island Harbour
With a stay at this vacation home in Shoal Bay, you'll be within a 5-minute drive of Shoal Bay Beach and Scilly Cay.
Your Anguilla Home! Homeaway from home-AI
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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.

Island Harbour 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 Island Harbour vacation homes are the perfect way for you to wing it.

Holiday houses in Island Harbour 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 Island Harbour 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 Island Harbour adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Island Harbour 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 Island Harbour 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.

Island Harbour Holiday Homes essential information

Accommodation
51 Holiday Homes
Lowest Price
AU$1,573
Highest Price
AU$1,573
Popular accommodation
DragonFly Studio, a charming place dedicated to relaxation, Spacious quiet house seconds from the beach, Paradise in Anguilla, Genesis Residences Meads Bay 1 - Downstairs Unit , White Sands Anguilla, Secluded house on private beach, White Sands Anguilla - 5 minute walk to beach, spacious, modern, and clean , Anguilla's "place to be" spacious 5-bedroom villa on upscale Meads Bay beach , Your Anguilla Home! Homeaway from home-AI

Top trending hotels in Island Harbour

The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach

The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach

Canifest
Located in Island Harbour, this apartment is within a 5-minute drive of Shoal Bay Beach and Scilly Cay.
The Penthouses (Sunrise and Sunset) at Andy’s Castle - near Shoal Bay Beach
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Island Harbour
When you stay at this villa in Island Harbour, you'll be by the ocean, within a 5-minute drive of Island Harbor Beach and Scilly Cay.
Caribbean Rhapsody Villa, Oceanfront Island Harbour 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.
Zen is Private, Tranquil, and Perfectly Located near Shoal Bay Beach!
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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$1,573 per night from 22 May to 23 May
AU$1,573
includes taxes & fees
22 May - 23 May
When you stay at Four Seasons Resort and Residences Anguilla in West End Village, you'll be on the beach and 10.6 mi (17.1 km) from Shoal Bay Beach.
Four Seasons Resort and Residences Anguilla
Don't see what you're looking for?
See all available properties in Island Harbour
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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.