Book Holiday Homes in Island Harbour

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Island Harbour

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
Save an average of 15% on thousands of hotels when you're signed in
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 and within a 5-minute drive of 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!
Don't see what you're looking for?
See all available properties in Island Harbour
View all properties
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
45 Holiday Homes
Lowest Price
AU$6,020
Highest Price
AU$6,020
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 Island Harbour

Lovely 6-bedroom Villa with Pool

Lovely 6-bedroom Villa with Pool

Island Harbour Anguilla
The price is AU$6,020 per night from 26 Dec to 27 Dec
AU$6,020
26 Dec - 27 Dec
includes taxes & fees
Located in Island Harbour, this villa is within a 5-minute drive of Scilly Cay and Shoal Bay Beach.
Opens in a new windowLovely 6-bedroom Villa with Pool
Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families

Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families

Island Harbour Anguilla
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.
Opens in a new windowClearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Island Harbour Anguilla
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.
Opens in a new windowCaribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!
Save an average of 15% on thousands of hotels when you're signed in
Clearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!

Clearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!

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.
Opens in a new windowClearview Villas (LOWER): Casual, Bright, Steps from Sea, Great for families!
Don't see what you're looking for?
See all available properties in Island Harbour
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.