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
Stay at this vacation home in The Valley. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Scrub Island and Stone Cellar Art Gallery ...
DragonFly Studio, a charming place dedicated to relaxation
Spacious quiet house seconds from the beach

Spacious quiet house seconds from the beach

Sandy Ground
Stay at this vacation home in The Valley. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Meads Bay and Crocus Bay are located ...
Spacious quiet house seconds from the beach
Paradise in Anguilla

Paradise in Anguilla

Sandy Hill
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 ...
Paradise in Anguilla
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Genesis Residences 
Meads Bay 1 - Downstairs Unit

Genesis Residences Meads Bay 1 - Downstairs Unit

The Cove
Stay at this vacation home in Cove Bay. Enjoy air conditioning. Popular attractions Meads Bay and Meads Bay Pond are located nearby.
Genesis Residences Meads Bay 1 - Downstairs Unit
White Sands Anguilla

White Sands Anguilla

3.5 out of 5
Cul De Sac Road, Blowing Point
Stay at this 3.5-star business-friendly vacation home in Blowing Point. Enjoy free WiFi, free parking, and a garden. Popular attractions Meads Bay and Grand ...
White Sands Anguilla
Secluded house on private beach

Secluded house on private beach

Sandy Ground
Book a stay at this beach vacation home in The Valley. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Meads Bay and Crocus Bay are located ...
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
Book a stay at this beach vacation home in Blowing Point. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Meads Bay and Grand Case 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

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

2 out of 5
West End
Stay at this vacation home in West End Village. Enjoy air conditioning. Popular attractions Meads Bay and Meads Bay Pond are located nearby.
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
Stay at this vacation home in Shoal Bay. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Shoal Bay Beach and Island Harbor Beach are ...
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
NZ$1,704
Highest Price
NZ$1,704
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
Stay at this apartment in Island Harbour. Enjoy free WiFi, breakfast (surcharge), and patios. Popular attractions Shoal Bay Beach and Island Harbor Beach are ...
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
Stay at this villa in Island Harbour. Enjoy private pools, balconies, and an in-room coffeemaker. Popular attractions Scilly Cay and Island Harbor Beach are ...
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
Stay at this vacation home in Island Harbour. Enjoy balconies, an in-room coffeemaker, and air conditioning. Popular attractions Shoal Bay Beach and Island Harbor ...
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 NZ$1,704 per night from 22 May to 23 May
NZ$1,704
includes taxes & fees
22 May - 23 May
Stay at this 5-star luxury resort in West End Village. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. ...
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.